Events in Easton, MD

● Listings verifiedThursday, September 17 · every listing checked against its source by our Easton editors

57This week
120Next 30 days
8Free this week
67Venues tracked

This weekend in Easton

The ones worth planning around. All 20 weekend events →

Free events in Easton

8 of this week's 57 events cost nothing. See all 8 free events →

  • Thu 3:30pm

    KENT ISLAND FARMERS' MARKET at Cult Classic

    Cult Classic Brewing, 1169 Shopping Center Rd, Stevensville · verified Sep 13
    Free

    A weekly, year-round farmers market sets up at Cult Classic Brewing each Thursday. Visitors will find a broad selection of foods, including an olive bar, grass-fed meat options, eggs, artisan sourdough bread, and cheeses. Vendors also provide refills for home and body care products, along with other offerings.

    Event website ↗
  • Thu 6pm

    [Easton] Board Game Club Night

    415 E Dover St, Easton · verified Sep 13
    Free

    Portals in Easton hosts a board game night that brings people together to play and socialize. It is free for customers, making it an easy way to step out and try something new. A community Discord is available to connect with others who share the same interests.

    Event website ↗
  • Sat 7am

    Running and Walking Club - Saturdays with Run Unleashed

    Talbot County Board of Education, 12 Magnolia St, Easton · verified Sep 13
    Free

    This free running and walking club partners with Talbot Humane’s Run Unleashed for a relaxed trail outing followed by coffee. It welcomes people who are beginning a fitness routine, working on endurance, or looking to connect with others. The atmosphere is inclusive, and participants choose the pace that feels right for them.

    Event website ↗
  • Sat 9am

    Benedictine's Chrome City Fundraiser Car & Motorcycle Show 2026

    14299 Benedictine Ln, Ridgely · verified Sep 13
    Free

    Benedictine’s Chrome City car and motorcycle show raises funds to support children and adults with intellectual and developmental disabilities and autism, helping them pursue their fullest potential. The event highlights custom and classic cars, hot rods, and motorcycles, and includes a mile-long cruise along the lane on the Benedictine campus. Spectators are welcome at no charge. Vehicle entry is $35 with online registration or $40 when registering on the day, and each registration includes a commemorative T-shirt. The first 50 cars to register will also receive a car plaque. Food and beverages will be available for purchase from Uncle Bernie’s Steak Shack, Walker Family Seafood, Isiah’s Ice Cream, Batty’s Brews, Smokin on the Shore, Jimmys Fat Rolls, Belly Bustin Grill, Shore Pop Kettle Corn, and Pages & Pours. For more information, contact Amy Pippin at 410-634-2292 or amy.pippin@benschool.org.

    Event website ↗

Live music in Easton

7 shows this weeksee the full live-music calendar →

  • Fri 7:30pm

    Unofficial Baygrass Pre-Party w/ The Wharf Rats, Live!

    Cult Classic Brewing, 1169 Shopping Center Rd, Stevensville · verified Sep 13
    See details

    The Wharf Rats bring an unofficial Baygrass pre-party to Cult Classic Brewing, channeling the vibe of Dead and DeadGrass in the classic Garcia and Grisman acoustic tradition. Expect an energetic set that invites dancing and a chance to let your Love Light shine as the Baygrass weekend approaches. Reserved seating is $20 per person, and general admission standing is $10 in advance or $15 at the door. Shortly before the performance begins, any unchecked tickets may be released to the standby list. The taproom features more than 15 house-brewed beers, a full bar, and a kitchen serving scratch-made pizza, house-pressed burgers, and jumbo wings made fresh, never frozen, so arriving early is a great way to enjoy food and drinks. Guests who need accessibility or special accommodations can inform staff at the door. Shows are all ages unless otherwise noted. Dogs are welcome on the patio but not inside the building. All sales are final, with refunds or exchanges only if a show is cancelled, and support acts along with set times may change.

    Event website ↗
  • Sat 5pm

    Music on the Marshyhope

    Marina Park Federalsburg, Md, Federalsburg · verified Sep 13
    Free

    Settle in by the water at Marina Park in Federalsburg for live music from Turning Point. Bring a chair and some friends, take in the fresh air, and enjoy the small-town charm as the music drifts along the Marshyhope.

    Event website ↗
  • Sat 5pm

    Live Music at Bridges: The Wombmates

    Bridges Restaurant, 321 Wells Cove Rd, Grasonville · verified Sep 13
    Free

    Bridges Restaurant in Kent Narrows hosts live music from The Wombmates, a live looping duo that creates a full-band sound with just two musicians. Guitars, vocals, and real-time loops come together as songs are built on the spot, keeping things upbeat and engaging for a dinner and drinks crowd. Enjoy a relaxed waterfront setting with a bar and restaurant atmosphere, and note that the show is free.

    Event website ↗
  • Sat 7pm

    Federalsburg VFW

    VFW POST 5246 Federalsburg MD, 2630 Veterans Drive, Federalsburg · verified Sep 13
    See details

    Southbound presents a set blending classic country with classic and southern rock. Enjoy a performance focused on these genres.

    Event website ↗

All upcoming events, day by day

Every event we track in Easton this week, in order. After one kind of thing? Live music and family events have their own calendars.

Thursday, September 17 9 events
  • 3:30pm

    KENT ISLAND FARMERS' MARKET at Cult Classic

    Cult Classic Brewing, 1169 Shopping Center Rd, Stevensville · verified Sep 13
    Free

    A weekly, year-round farmers market sets up at Cult Classic Brewing each Thursday. Visitors will find a broad selection of foods, including an olive bar, grass-fed meat options, eggs, artisan sourdough bread, and cheeses. Vendors also provide refills for home and body care products, along with other offerings.

    Event website ↗
  • 4pm

    Happy Hour at Theo's

    407 S Talbot St, St Michaels · verified Sep 13
    See details

    Theo’s Happy Hour offers select cocktails, beer, wine, and bites at set prices. Choose a Cosmo for $8, a Pear-tini for $10, or an Old Fashioned for $8. Domestic beer bottles are $4 and wines by the glass are $5. Food options include Filet Sliders for $12, Caroline’s Fried Pickles for $5, Lemon Pepper Edamame (GF) for $8, Potato Skins (GF) for $5, and Fried Bell Pepper Rings for $9. Happy Hour Half Plates present house classics in a smaller portion, with Steak Roquefort or Steak Diane at $20 each. Burgers are also $5 off.

    Event website ↗
  • 6pm

    [Kent Island] Tabletop Thursday!

    146 Kent Lndg, Stevensville · verified Sep 13
    See details

    Weekly tabletop groups come together for games and conversation in a welcoming, ever-growing community. It is a friendly space to connect with like-minded people and enjoy tabletop play.

    Event website ↗
  • 6pm

    [Easton] Board Game Club Night

    415 E Dover St, Easton · verified Sep 13
    Free

    Portals in Easton hosts a board game night that brings people together to play and socialize. It is free for customers, making it an easy way to step out and try something new. A community Discord is available to connect with others who share the same interests.

    Event website ↗
  • 6pm

    THURSDAY NIGHT TRIVIA at CULT

    Cult Classic Brewing, 1169 Shopping Center Rd, Stevensville · verified Sep 13
    See details

    Trivia night at Cult Classic Brewing brings three standard rounds followed by a finale where teams can bet their points. Questions can cover any subject. The top three finishers receive prizes that may include gift cards, tequila shots, bragging rights, high fives, and a mix of quirky finds from the back. Phone use is prohibited and the Quizzard has the last word, keeping the match lively and fair for teams and trivia enthusiasts.

    Event website ↗
  • 6pm

    Lorcana Thursday Night League

    8223 Elliott Rd, Easton · verified Sep 13
    See details

    A weekly casual Lorcana tournament anchors the Thursday Night League. This is a Constructed event run in Swiss format with a $5 entry. Every entry includes a pack, and each win earns an additional pack. Weekly league promos are available, limited to one per week. There is also a second Lorcana night on Friday, and players are welcome on both nights.

    Event website ↗
  • 6:30pm

    [Easton] Yu-Gi-Oh! TCG Triple Prize Tournament

    415 E Dover St, Easton · verified Sep 13
    See details

    Compete in a Yu-Gi-Oh! TCG triple prize tournament with a $12 entry fee. Each participant receives three OTS packs, and if OTS packs are in short supply some will be substituted with other promotional packs.

    Event website ↗
  • 6:30pm

    [Easton] Yu-Gi-Oh! Weekly Tournament

    415 E Dover St, Easton · verified Sep 13
    See details

    This weekly Yu-Gi-Oh! tournament features prize support at every event. A Discord community is available to connect with fellow fans.

    Event website ↗
  • 7pm

    [Easton] One Piece TCG Tournament

    415 E Dover St, Easton · verified Sep 13
    See details

    A One Piece trading card game tournament will be held in a Best of 1 Standard format. Players face off in head-to-head matches that follow the standard ruleset for competitive play.

    Event website ↗
Friday, September 18 8 events
  • 6:30am

    Dogs in the Drive-Thru

    1845 Main St, Chester · verified Sep 13
    See details

    Chick-fil-A Kent Island is celebrating four-legged friends with a drive-thru treat. Bring your dog along when placing an order in the drive-thru and receive a small gift with a purchase, available while supplies last.

    Event website ↗
  • 1pm

    Canasta

    210 Vincit St, Centreville · verified Sep 13
    See details

    Settle in for a friendly round of Canasta, a classic game related to Rummy. If you already play Hand and Foot, the rules will feel familiar. All cards are provided and there will be plenty of company, so just bring yourself. Participation is limited to members of the QAC Senior Center or the Active Aging Center, and anyone 55 or older can sign up for a free membership.

    Event website ↗
  • 6pm

    [Kent Island] Magic the Gathering: Casual Commander

    146 Kent Lndg, Stevensville · verified Sep 13
    See details

    Space is set aside for relaxed Commander play in Magic: The Gathering. Players can stop in, find a table, and enjoy friendly games with others throughout the event. It offers a casual setting for like-minded Magic fans to connect and play at an easygoing pace.

    Event website ↗
  • 6pm

    [Kent Island] MTG: Commander Checklist Challenge

    146 Kent Lndg, Stevensville · verified Sep 13
    See details

    Take on a Commander Checklist Challenge that rewards both knowledge and play. Tackle Commander themed objectives to earn prizes, with a Set Booster pack for every participant. Answer six or more questions to receive a magic promo. Entry is $6.

    Event website ↗
  • 7pm

    One Piece Weekly Friday Tournament

    8223 Elliott Rd, Easton · verified Sep 13
    See details

    Compete in a casual One Piece constructed tournament run in a Swiss format over three rounds. Matches are best of one, each round lasts 30 minutes with a 5 minute overtime extension. Entry is $5, with capacity capped at 64 players. Players earn a booster pack for every match win and can take advantage of player-only deals in store. Prize support changes from event to event and may include booster packs, exclusive tournament packs, and extra raffles. Participation requires the BANDAI TCG+ app, so create an account on a mobile device in advance and complete preregistration through the app. A community Discord is available for ongoing updates.

    Event website ↗
  • 7pm

    [Easton] MTG Casual Commander Night

    415 E Dover St, Easton · verified Sep 13
    See details

    Space is dedicated to casual Commander play in Magic: The Gathering. Players can meet others and play games together in an open setting. There is also a Discord community for those who want to connect between sessions.

    Event website ↗
  • 7pm

    Pony Express Speed Show Series - Show #5

    Queen Anne's County 4-H Fair, 106 Dulin Clark Rd, Centreville · verified Sep 13
    See details

    The fifth show in this speed series offers five classes, including Barrels, Texas Barrels, Poles, and Plug or a class to be announced. Entries are $20 each. Riders of all ages are welcome, with divisions for lead line, junior, intermediate, senior, and adult. Points earned at this show count toward year-end high point awards. The event follows 4-H Horse and Pony Rules and invites support for the Queen Anne’s County Pony Express 4-H club. The series continues through spring and fall with scheduled rain dates.

    Event website ↗
  • 7:30pm

    Unofficial Baygrass Pre-Party w/ The Wharf Rats, Live!

    Cult Classic Brewing, 1169 Shopping Center Rd, Stevensville · verified Sep 13
    See details

    The Wharf Rats bring an unofficial Baygrass pre-party to Cult Classic Brewing, channeling the vibe of Dead and DeadGrass in the classic Garcia and Grisman acoustic tradition. Expect an energetic set that invites dancing and a chance to let your Love Light shine as the Baygrass weekend approaches. Reserved seating is $20 per person, and general admission standing is $10 in advance or $15 at the door. Shortly before the performance begins, any unchecked tickets may be released to the standby list. The taproom features more than 15 house-brewed beers, a full bar, and a kitchen serving scratch-made pizza, house-pressed burgers, and jumbo wings made fresh, never frozen, so arriving early is a great way to enjoy food and drinks. Guests who need accessibility or special accommodations can inform staff at the door. Shows are all ages unless otherwise noted. Dogs are welcome on the patio but not inside the building. All sales are final, with refunds or exchanges only if a show is cancelled, and support acts along with set times may change.

    Event website ↗
Saturday, September 19 18 events
  • 7am

    Running and Walking Club - Saturdays with Run Unleashed

    Talbot County Board of Education, 12 Magnolia St, Easton · verified Sep 13
    Free

    This free running and walking club partners with Talbot Humane’s Run Unleashed for a relaxed trail outing followed by coffee. It welcomes people who are beginning a fitness routine, working on endurance, or looking to connect with others. The atmosphere is inclusive, and participants choose the pace that feels right for them.

    Event website ↗
  • 7am

    Saturday Sisterhood Walk

    627 Race St, Cambridge · verified Sep 13
    See details

    Each week, walkers team up with the Groove City Trekkers in the Home of Harriet Tubman for a simple, supportive way to invest in health. The focus is walking as a powerful tool... it can help lower high blood pressure, assist with preventing and managing diabetes, ease stress, and strengthen the heart. The experience also draws inspiration from Harriet Tubman, who traveled countless miles on foot to lead others to freedom and lived to the age of 93, a testament to resilience and purpose. New and seasoned walkers alike are welcome in a no pressure setting centered on movement, motivation, and community. Every Saturday offers another chance to take steps for personal wellness, families, and the future.

    Event website ↗
  • 8:30am

    2026 We R Family Annual Crab Feast

    Fisherman's Crab Deck, 3032 Kent Narrows Way S, Grasonville · verified Sep 13
    See details

    A full-day outing blends shopping, seafood, and waterfront time. It starts at Queenstown Premium Outlets to browse for bargains, continues at Fisherman's Crab Deck for a crab feast, and wraps up at National Harbor, MD, with choices that include a stroll by the water, gaming at MGM Casino Resort, or more shopping at Tanger Outlets.

    Event website ↗
  • 9am

    2026 CPM Race Week - Region 2 Championship

    Cedar Point Marina, 3420 Main Street, Grasonville · verified Sep 13
    See details

    https://www.theamya.org/RegattaDetail.asp?RGID=10692

    Event website ↗
  • 9am

    Pinked Perspective Kit Assembly Event

    Benedict A. Andrew American Legion Post #296, 6200 Main St, Queenstown · verified Sep 13
    See details

    The Pinked Perspective kit assembly party brings people together to prepare kits for those newly diagnosed with breast cancer. All supplies are provided, and refreshments including coffee, juice, and donuts will be available. Volunteer registration is requested.

    Event website ↗
  • 9am

    Benedictine's Chrome City Fundraiser Car & Motorcycle Show 2026

    14299 Benedictine Ln, Ridgely · verified Sep 13
    Free

    Benedictine’s Chrome City car and motorcycle show raises funds to support children and adults with intellectual and developmental disabilities and autism, helping them pursue their fullest potential. The event highlights custom and classic cars, hot rods, and motorcycles, and includes a mile-long cruise along the lane on the Benedictine campus. Spectators are welcome at no charge. Vehicle entry is $35 with online registration or $40 when registering on the day, and each registration includes a commemorative T-shirt. The first 50 cars to register will also receive a car plaque. Food and beverages will be available for purchase from Uncle Bernie’s Steak Shack, Walker Family Seafood, Isiah’s Ice Cream, Batty’s Brews, Smokin on the Shore, Jimmys Fat Rolls, Belly Bustin Grill, Shore Pop Kettle Corn, and Pages & Pours. For more information, contact Amy Pippin at 410-634-2292 or amy.pippin@benschool.org.

    Event website ↗
  • 9:30am

    Log Canoe Spectator Cruise

    213 N Talbot St, St Michaels · verified Sep 13
    See details

    A cruise aboard the PATRIOT offers views of traditional log canoe racing on the Miles River. From the deck, participants see these distinctive Chesapeake vessels under sail while experienced sailors describe the tactics, traditions, and action as it unfolds. It is suitable for longtime fans and for those new to this time honored tradition. The cruise follows PATRIOT’s standard cancellation and refund policies. If the races are canceled or the schedule changes, the boat still travels the Miles River and an experienced log canoe sailor provides insights throughout the trip.

    Event website ↗
  • 10am

    Walk to End Alzheimer's

    Idlewild Park, Easton · verified Sep 13
    See details

    This community walking event at Idlewild Park is dedicated to ending Alzheimer’s. Participants may walk with a team or support the cause by making a donation.

    Event website ↗
  • 10:15am

    IRONMAN MD Bike Aid Station

    Christ Rock Park, Cambridge MD, Cambridge · verified Sep 13
    Free

    At the final bike course aid station before T2, athletes are deep into the effort and encouragement can make a real difference. MMTC has supported this exact station since before it was part of IRONMAN, and it remains a lively place to experience the race up close. Volunteers help hand out water, play music, and cheer riders through a crucial stretch around Mile 100, giving back to the community while helping competitors reach the next transition.

    Event website ↗
  • 11am

    ESSM 1st Annual Car Show

    Cult Classic Brewing, 1169 Shopping Center Rd, Stevensville · verified Sep 13
    See details

    Cult Classic Brewing hosts a first-year car show raising funds for Amy’s Army. Cars, trucks, and bikes of any make or model are invited to participate, with a $15 registration fee for cars and motorcycles. Expect rows of standout vehicles, vendor booths, raffles, trophies, and family-friendly activities, all in support of a local charity. Redline Performance and Chesapeake Classic Restorations are sponsoring the trophies and taking part. Show off your ride, connect with fellow enthusiasts, and help direct every dollar raised to Amy’s Army.

    Event website ↗
  • 5pm

    Music on the Marshyhope

    Marina Park Federalsburg, Md, Federalsburg · verified Sep 13
    Free

    Settle in by the water at Marina Park in Federalsburg for live music from Turning Point. Bring a chair and some friends, take in the fresh air, and enjoy the small-town charm as the music drifts along the Marshyhope.

    Event website ↗
  • 5pm

    Live Music at Bridges: The Wombmates

    Bridges Restaurant, 321 Wells Cove Rd, Grasonville · verified Sep 13
    Free

    Bridges Restaurant in Kent Narrows hosts live music from The Wombmates, a live looping duo that creates a full-band sound with just two musicians. Guitars, vocals, and real-time loops come together as songs are built on the spot, keeping things upbeat and engaging for a dinner and drinks crowd. Enjoy a relaxed waterfront setting with a bar and restaurant atmosphere, and note that the show is free.

    Event website ↗
  • 5pm

    [Easton] Shadowverse Evolve Tournament

    415 E Dover St, Easton · verified Sep 13
    See details

    This event features competitive Shadowverse: Evolve play in the standard format with single-game matches and 35 minute rounds. Casual play takes place beforehand. Entry is $5, and prize support is included.

    Event website ↗
  • 6pm

    Dreams to Doorways benefit for Mid-Shore Love Down Payment Grant Program

    Miles River Yacht Club, 24750 Yacht Club Rd, Saint Michaels · verified Sep 13
    See details

    This polished night features cuisine, lighthearted fun, and time on the dance floor, all in support of local homeownership. It is a celebration with purpose, bringing people together to enjoy food and music while backing this community-focused cause.

    Event website ↗
  • 6:30pm

    [Kent Island] One Piece TCG Tournament

    146 Kent Lndg, Stevensville · verified Sep 13
    See details

    Players compete in best-of-one matches using the standard format of the One Piece trading card game. The entry fee is $5, with prizes distributed as packs or store credit.

    Event website ↗
  • 7pm

    Federalsburg VFW

    VFW POST 5246 Federalsburg MD, 2630 Veterans Drive, Federalsburg · verified Sep 13
    See details

    Southbound presents a set blending classic country with classic and southern rock. Enjoy a performance focused on these genres.

    Event website ↗
  • 7pm

    [Easton] Weiss Schwarz Playmat Tournament

    415 E Dover St, Easton · verified Sep 13
    See details

    Players can gather for a Weiss Schwarz tournament using the standard format, with single-game matches and rounds lasting 35 minutes. Casual matches are available beforehand for warmups and practice. One participant will be randomly selected to receive a Weiss Schwarz playmat. Entry is $5 and includes prize support.

    Event website ↗
  • 7pm

    [Easton] Weiss Schwarz Weekly Tournament

    415 E Dover St, Easton · verified Sep 13
    See details

    This weekly Weiss Schwarz tournament features the Neo-Standard format. It follows a Swiss structure with three rounds, each best of one and 35 minutes. Participants can arrive early to register and play casual games before the event begins. Entry is $5. A Discord community is available for announcements and conversation.

    Event website ↗
Sunday, September 20 2 events
  • 9am

    Easton, MD Cars & Coffee

    Easton VFW Post 5118, 367 Glebe Rd, Easton · verified Sep 13
    See details

    This relaxed gathering features coffee, conversation and a variety of automobiles in a welcoming setting. It is open to everyone and to vehicles of every kind. The event takes place at Easton VFW Post 5118, with updates shared as they become available.

    Event website ↗
  • 2pm

    Justin Taylor | Kent Island MD

    Libbey's Coastal Kitchen + Cocktails, 357 Pier One Road, Stevensville · verified Sep 13
    See details

    Justin Taylor performs a solo acoustic set at Libbey's Coastal Kitchen + Cocktails on Kent Island. This is a solo performance with an acoustic sound.

    Event website ↗
Monday, September 21 3 events
  • 6pm

    [Kent Island] Disney Lorcana TCG Tournament

    146 Kent Lndg, Stevensville · verified Sep 13
    See details

    Players face off in a weekly Disney Lorcana trading card game tournament with 50 minute rounds using a best of three structure. The entry fee is $7. Weekly prizes include packs and league points. Extra prizing is based on points at the end of every four weeks, with additional season-end awards after twelve weeks.

    Event website ↗
  • 6pm

    [Easton] RPG Night!

    Portals Games & Comics, 415 E Dover St, Easton · verified Sep 13
    See details

    Weekly RPG nights feature open-table play led by volunteer Game Masters. Each table accommodates up to six players, and offerings vary by GM. Arriving a little early makes it easier to introduce yourself, find out what is running, and see if a seat is available. Space can be limited, so checking availability in advance is recommended. Entry is $3.

    Event website ↗
  • 6pm

    [Kent Island] MTG: Casual Commander

    146 Kent Lndg, Stevensville · verified Sep 13
    See details

    Open play is dedicated to casual Commander, with space set aside for pickup games. Magic: The Gathering players can meet others and enjoy friendly matches. A Discord community is available for like-minded players.

    Event website ↗
Tuesday, September 22 13 events
  • 2pm

    Birding & Boating Along the Harriet Tubman Byway

    Linchester Mill, 3400 Linchester Rd, Preston · verified Sep 13
    See details

    A guided, self-driven outing with Harriet Tubman Tours and Delmarva Birding Weekends blends birding with history along the Harriet Tubman Underground Railroad Byway in Caroline County, Maryland. During the first two hours, participants learn about escapes led by Harriet Tubman, a freedom seeker and human rights activist often called the Moses of her people, and about the assistance she received in the county while traveling toward Delaware. The drive passes farms, forests, and significant Underground Railroad sites in Caroline County, concluding at River Run Cruises in Denton. From there, River City Cruise Co. leads a two-hour pontoon excursion on the upper Choptank River, where downriver landings once supported escapes by boat and shallow stretches upstream offered crossings for those moving north toward Sandtown, Delaware.

    Event website ↗
  • 5pm

    Bingo

    American Legion Caroline Post 29, 9238 Legion Rd, Denton · verified Sep 13
    See details

    At Caroline Post 29, bingo features a $25 entry covering all regular games. Doors open before play begins. Early Bird rounds come first, followed by the regular session. Food will be available to buy, and all are welcome.

    Event website ↗
  • 5pm

    EVERY TUESDAY on Kent Island

    Rita's Italian Ice & Frozen Custard (Kent Island, MD), 210 Kent Lndg, Stevensville · verified Sep 13
    See details

    Every Tuesday, weather permitting, Rita’s Italian Ice & Frozen Custard on Kent Island becomes a casual cruise-in spot where vintage and specialty rides roll in and park for everyone to check out. The mix of cars changes from week to week, creating a relaxed scene for enthusiasts and curious onlookers alike. Keep an eye out for Super Tuesday Benefit Cruise Nights as part of the series. Vehicles parked on the lot that qualify as old rides receive a buy one, get one offer from Rita’s, except during the benefit nights.

    Event website ↗
  • 6pm

    [Easton] Disney Lorcana Weekly Tournament

    415 E Dover St, Easton · verified Sep 13
    See details

    This weekly Disney Lorcana tournament spotlights the Core format with a Swiss structure across three rounds. Each round is best of three and capped at 50 minutes. Entry is $7. Signups take place beforehand, with time for casual matches before the main competition. Prizes are awarded each week based on attendance, with extra prize support offered every three months.

    Event website ↗
  • 6pm

    [Easton] Magic the Gathering: Casual Commander

    Portals Games & Comics, 210 Marlboro Ave, Easton · verified Sep 13
    See details

    This relaxed Magic: The Gathering meetup at Portals Games & Comics opens the play space for casual games in any style and welcomes all experience levels. Commander is the primary focus, with plenty of opportunities to break out favorite decks and form pods with other participants.

    Event website ↗
  • 6pm

    Kent Island Writer's Cult '26

    Cult Classic Brewing, 1169 Shopping Center Rd, Stevensville · verified Sep 13
    See details

    At Cult Classic Brewing, the Kent Island Writers Cult brings together novelists, compilers of collections, children’s book illustrators, and fan fiction creators for a supportive session focused on craft and community. Participants can share pages from works in progress, exchange feedback, connect with local authors, and build a network aimed at publishing goals. Each gathering features a different local author who hosts the session, curates readings, answers questions, and offers encouragement.

    Event website ↗
  • 6pm

    [Kent Island] Pokémon TCG Weekly Tournament

    146 Kent Lndg, Stevensville · verified Sep 13
    See details

    A weekly Pokémon Trading Card Game tournament invites players to compete in Standard-format play using a Swiss pairing system with three rounds. Each round is a single game with a 30 minute limit. The entry fee is $5. Participants can arrive early to register and enjoy casual warm up matches before the tournament begins.

    Event website ↗
  • 6pm

    [Kent Island] Riftbound Nexus Night!

    146 Kent Lndg, Stevensville · verified Sep 13
    See details

    This weekly event features Riftbound tournaments.

    Event website ↗
  • 6pm

    [Easton] Magic the Gathering: Commander Checklist Challenge

    415 E Dover St, Easton · verified Sep 13
    See details

    Each week, this Magic: The Gathering Commander event features a checklist-style challenge. Players receive a fresh set of in-game objectives to pursue during their matches, and trying different decks can help complete more of them. The total objectives finished determines how many promo cards are awarded at the end. Entry is the purchase of any Magic: The Gathering booster pack.

    Event website ↗
  • 6:30pm

    [Easton] Star Wars Unlimited Weekly Tournament

    415 E Dover St, Easton · verified Sep 13
    See details

    This weekly Star Wars Unlimited tournament uses a constructed format. Matches follow Swiss pairings with single-game rounds capped at 25 minutes. Entry is $5.

    Event website ↗
  • 7pm

    [Kent Island] Union Arena Weekly Tournament

    146 Kent Lndg, Stevensville · verified Sep 13
    See details

    Participants will compete in a Union Arena tournament using a Best of 1 format with 30 minute Swiss rounds. Prizes will be awarded as store credit.

    Event website ↗
  • 7pm

    One Piece Weekly Tuesday Tournament

    Two Pair Collectibles, 8223 Elliott Rd, Easton · verified Sep 13
    See details

    Take part in a casual One Piece constructed tournament run as three Swiss rounds. Matches are best of one, each round is 30 minutes with a 5 minute overtime extension. Entry is $5, and capacity is capped at 64 players. The BANDAI TCG+ app is required, so set up an account in advance and complete preregistration through the app. Players earn one booster pack for each match win and can access exclusive in-store deals for participants. Prize support varies by event and may include booster packs, exclusive tournament packs, and additional raffles.

    Event website ↗
  • 7:30pm

    Cult’s Open Mic 2026

    Cult Classic Brewing Company, Stevensville · verified Sep 13
    See details

    An open mic at Cult Classic gives hidden talents a chance to step into the spotlight. Performers typically take the stage for a brief set of up to three songs, with encores possible. The venue supplies a full stage with professional lights and sound, some backline for musicians, and an HDMI connection for the projector. Admission is free, and even the green room gets careful treatment. The lineup is unpredictable, so every show can bring something different.

    Event website ↗
Wednesday, September 23 4 events
  • 6pm

    [Kent Island] Yu-Gi-Oh! TCG Weekly Tournament

    146 Kent Lndg, Stevensville · verified Sep 13
    See details

    Take part in a weekly Yu-Gi-Oh! TCG tournament run in a Swiss format with three rounds. Each round is a best-of-three match with a 50-minute time limit. Entry is $5. Signups are available on site, with casual games before the tournament.

    Event website ↗
  • 6pm

    Music Bingo

    Rams Head Shore House, 800 Main St, Stevensville · verified Sep 13
    See details

    Enjoy a round of music bingo hosted by DJ Juice. Listen to each track, mark the matching song title on your card, and try to be the first to call bingo. Fun for participants of all ages.

    Event website ↗
  • 6pm

    [Easton] Riftbound Nexus Night!

    415 E Dover St, Easton · verified Sep 13
    See details

    A weekly Riftbound tournament offering friendly competition and a chance to connect with fellow players. This recurring event focuses on gameplay and community, providing a consistent opportunity to compete and have fun.

    Event website ↗
  • 6pm

    Running and Walking Club

    Idlewild Park, 510 S Aurora St, Easton · verified Sep 13
    Free

    Talbot Thrive teams up with the Town of Easton Parks and Recreation Department, the University of Maryland Shore Regional Health Center, and the YMCA of the Chesapeake to host a free community running and walking club at Idlewild Park in Easton. This welcoming gathering brings people together to support both physical and mental wellbeing. Participants can choose to walk or run the park trail at a comfortable pace, creating an inclusive atmosphere for newcomers and experienced athletes to connect while working toward personal fitness goals.

    Event website ↗

All upcoming events104 more events through Dec 11

Everything else on Easton's calendar over the next 30 days, in order.

Thursday, September 24 7 events
  • 6pm

    Board Game Club Night

    Portals Games & Comics, 415 E Dover St, Easton · verified Sep 13
    Free

    Portals in Easton hosts a free board game night that offers a relaxed setting to play and explore something new while meeting others with similar interests. A Discord community is available for connecting with fellow attendees.

    Event website ↗
  • 6pm

    [Kent Island] Tabletop Thursday!

    146 Kent Lndg, Stevensville · verified Sep 13
    See details

    Weekly tabletop groups come together to connect and have fun. It is a simple way to meet others who share your interests and be part of a community that keeps growing. A Discord community is available for staying in touch between gatherings.

    Event website ↗
  • 6pm

    Lorcana Thursday Night League

    Two Pair Collectibles, 8223 Elliott Rd, Easton · verified Sep 13
    See details

    Enjoy a casual Lorcana tournament set up for weekly league play. This constructed event uses a Swiss format, and entry is $5. Participants receive a pack with entry and another pack for each win. Weekly league promos are available, limited to once per week, and all players are welcome on both nights. A second Lorcana night is also offered on Friday.

    Event website ↗
  • 6:30pm

    Thursdays Line Dancing 2026

    Cult Classic Brewing, 1169 Shopping Center Rd, Stevensville · verified Sep 13
    See details

    Enjoy a lively night of line dancing with a $5 entry. Beginners start with a focused lesson to learn the basics or refresh their steps, then the floor opens up so everyone can practice while Sandy keeps the music going and the rhythm steady. Cult Classic serves more than 15 house-brewed beers alongside a full bar, and the kitchen features from-scratch pizza, hand-formed burgers, and jumbo wings made from fresh, never frozen chicken. All sales are final. Refunds or exchanges are offered only if a show is cancelled, and support acts and scheduling may change.

    Event website ↗
  • 6:30pm

    [Easton] Yu-Gi-Oh! Weekly Tournament

    415 E Dover St, Easton · verified Sep 13
    See details

    This recurring Yu-Gi-Oh! tournament brings duelists together for friendly competition each week. Prizes are awarded at every tournament. A Discord community is available for connecting with other players.

    Event website ↗
  • 7pm

    The Wailers

    The Avalon, 40 E Dover Street, Easton · verified Sep 13
    See details

    The Wailers bring their uplifting reggae sound to The Avalon with a tribute to the 50th anniversary of Rastaman Vibration. The 50 Years of Positive Vibrations tour showcases choice selections from the landmark 1976 album alongside enduring hits that connect listeners across generations. Rastaman Vibration helped carry reggae’s messages of resistance, spirituality, and hope to audiences worldwide, and songs such as Positive Vibration, Roots, Rock, Reggae, and War continue to resonate. This performance honors the legacy of Bob Marley & The Wailers and celebrates music with purpose, linking reggae’s golden era to its ongoing ability to inspire unity, resilience, and hope.

    Event website ↗
  • 7pm

    One Piece TCG Tournament

    Portals Games & Comics, 415 E Dover St, Easton · verified Sep 13
    See details

    This One Piece tournament features Best of 1 matchups in the Standard format. Participants compete in single-game rounds.

    Event website ↗
Friday, September 25 12 events
  • 11am

    19th Annual Concours d'Elegance

    Kent Island Yacht Club, 117 Yacht Club Dr, Chester · verified Sep 13
    See details

    Set on the waterfront lawn of Kent Island Yacht Club, the 19th annual Concours d’Elegance on Chesapeake Bay showcases classic automobiles alongside classic boats in a scenic bayside setting. The weekend highlights Chesapeake Bay yachting, with classic motor yachts and wooden speedboats on display. Entrant activities unfold across the weekend, and details about applications and sponsorship will be shared on the event website. The public portion takes place on the final day, offering spectators a chance to enjoy the displays on the lawn.

    Event website ↗
  • 11am

    2026 Chamber Challenge Golf Tournament

    River Marsh Golf Club, 100 Heron Blvd, Cambridge · verified Sep 13
    See details

    Hosted by the Dorchester Chamber of Commerce, the 36th edition of the Chamber Challenge Golf Tournament brings regional business owners and leaders together for a day of connection and 18 holes of golf at the Hyatt Regency Chesapeake Bay Resort and Spa. Multiple sponsorship packages are available for this signature tournament. Tournament sponsors include Best Wine & Spirits, Hill Kimmel Contracting, Whitten Retirement Solutions, and Shore United Bank. The Hole in One sponsor is Preston Automotive. Logo ball sponsors are Tides at Rivermarsh and Intyllus. The on-course bar is supported by Koski Enterprises, Inc. and Culta. Lunch support comes from Farm Creek Insurance and BayVanguard Bank. The reception is supported by Choptank Electric Coop. Oasis sponsors are Queenstown Bank and Lennar. Closest to the Pin is sponsored by R&M Performance. T-Hole sponsors include United Way of the Lower Eastern Shore, Layton's Chance, Amick Farms, DeLco Packaging, Ferry Point Marina, and Shore Iron Solutions. Appreciation goes to all sponsors for their generous support that helps make this event possible.

    Event website ↗
  • 3pm

    St Michaels Concours d'Elegance on the Chesapeake Bay 09/27/26

    Kent Island Yacht Club, 117 Yacht Club Drive, Chester · verified Sep 13
    See details

    The 19th annual concours on the Chesapeake Bay marks Bentley’s 100th anniversary, with classes for prewar automobiles and for postwar models through the 1976 model year. This multi-day gathering culminates with the concours on the waterfront at Kent Island Yacht Club. In a prior celebration, organizers marked the Rolls-Royce Phantom centenary and included some later examples to help educate the public. Bentley Washington D.C. is a sponsor. Organizers are interested in featuring notable Bentleys on the show field.

    Event website ↗
  • 5pm

    Food Truck Night

    Queenstown Town Center, 7013 Main St, Queenstown · verified Sep 13
    See details

    Food truck nights return with a relaxed gathering in the town parking lot in Queenstown, right next to the town office. The lineup of vendors and trucks changes from month to month, so look for the latest list as plans evolve. Enjoy your meal on site or take it to go, and know that every purchase supports local vendors and contributes to a good cause.

    Event website ↗
  • 5pm

    Friday Night Dinner & Live Music

    American Legion Caroline Post 29, 9238 Legion Rd, Denton · verified Sep 13
    See details

    American Legion Auxiliary Unit 29 hosts an evening of food, live music, and fellowship at American Legion Caroline Post 29. Guests can enjoy a Pork Sirloin Roast dinner with mac and cheese and peas for $12, followed by a performance from Sticky Situation. This gathering offers a hearty meal, lively entertainment, and time with neighbors.

    Event website ↗
  • 6pm

    "Opal's Pace"

    Campbell's Lane Farm, 22862 Dover Bridge Rd, Preston · verified Sep 13
    See details

    Opal’s Pace is an immersive western dinner show fundraiser that invites guests to slow down and let kindness take the lead. Set at Campbell’s Lane Farm, it blends humor, shared meals, storytelling, and community moments, with appearances by Opal the miniature donkey and her donkey friends to highlight the power of a gentler pace. The event includes a buffet prepared by Chesapeake Culinary Center, with dessert, tea, and water included, plus mocktails and dirty sodas available for purchase. Outdoor gathering spaces offer room to connect, there are opportunities to meet Opal and her companions, and the show features an intermission. Western attire is encouraged. Tickets are $85 per person with open seating. Ages 6 and up. Capacity is limited. Proceeds support Food For Learning and its backpack program addressing childhood food insecurity in Caroline County.

    Event website ↗
  • 6pm

    [Kent Island] Magic the Gathering: Casual Commander

    146 Kent Lndg, Stevensville · verified Sep 13
    See details

    An open play setting for Magic: The Gathering Commander, focused on casual games. The floor is reserved for friendly matchups, allowing players to find a table and enjoy relaxed Commander play with others.

    Event website ↗
  • 6pm

    MTG: Commander Checklist Challenge

    Portals Games & Comics, 146 Kent Lndg, Stevensville · verified Sep 13
    See details

    Take on the Commander Checklist Challenge and complete Commander themed objectives for a chance at rewards and prizes. Each participant receives a Set Booster pack, and answering six or more questions earns a promo. Entry is $6.

    Event website ↗
  • 7pm

    Brett Dennen

    The Avalon, 40 E Dover St, Easton · verified Sep 13
    See details

    Folk pop singer songwriter Brett Dennen brings his Art is Life tour to The Avalon with an intimate concert built around warm, soulful vocals, reflective lyrics, and stories rooted in lived experience. Presented in a no opening act format, the night features Dennen performing solo on acoustic guitar while integrating his own large scale paintings into the show. The audience plays a small but meaningful role by helping shape the set list and the arc of the storytelling, making each performance distinct.

    Event website ↗
  • 7pm

    [Easton] MTG Casual Commander Night

    415 E Dover St, Easton · verified Sep 13
    See details

    Open tables are set aside for casual Commander games, giving Magic: The Gathering players a chance to stop in and play. A community Discord is available for connecting with like minded players.

    Event website ↗
  • 7pm

    One Piece Weekly Friday Tournament

    Two Pair Collectibles, 8223 Elliott Rd, Easton · verified Sep 13
    See details

    Enjoy a casual One Piece card game tournament using a constructed format with Swiss pairings across three rounds. Matches are best of one, each round is 30 minutes, and a 5 minute overtime extension is available. Entry is $5 and the field is limited to 64 players. The BANDAI TCG+ app is required, so create an account in advance and use it to preregister. Participants receive one booster pack for each match win and can access exclusive in-store player deals. Prize support varies by event and may include booster packs, special tournament packs, and additional raffle prizes.

    Event website ↗
  • 8:30pm

    MCB

    Jetty Dock Bar, 201 Wells Cove Rd, Grasonville · verified Sep 13
    See details

    My Chemical Bromance returns to Jetty Dock Bar with a high energy show featuring a set of 2000s rock, pop punk, and emo.

    Event website ↗
Saturday, September 26 8 events
  • 7am

    Running and Walking Club - Saturdays

    Talbot County Board of Education, 12 Magnolia St, Easton · verified Sep 13
    Free

    A free running and walking club partners with Talbot Humane’s Run Unleashed for a trail outing that can be walked or run, followed by coffee. It is designed for people beginning a fitness journey, those working on endurance, and anyone seeking community. The atmosphere is welcoming, and participants choose the pace that feels right for them.

    Event website ↗
  • 10am

    Frederick Douglass Day 2026

    Talbot County Courthouse, 11 N Washington St, Easton · verified Sep 13
    Free

    A community celebration presented by the Frederick Douglass Honors Society honors Frederick Douglass, celebrated as Talbot County's most prominent son. Festivities begin with a parade that travels from Easton Elementary School to the County Courthouse. All events are free and open to the public.

    Event website ↗
  • 1pm

    NCHS Volleyball Alumni Tournament 2026

    North Caroline High School, 10990 River Rd, Ridgely · verified Sep 13
    See details

    The NCHS Volleyball Alumni Tournament returns to North Caroline High School with a Glow Volleyball format. Alumni players compete in a friendly tournament that adds a glowing twist to the game and keeps the focus on fun. Registration is open through the event organizers.

    Event website ↗
  • 5pm

    HVFCA/HVFC Family/Grocery Bingo

    Hurlock Volunteer Fire Company, 300 Charles St, Hurlock · verified Sep 13
    See details

    This family and grocery themed bingo event at Hurlock Volunteer Fire Company offers bingo books for $10, with extra books available for $5. A special raffle, a 50/50, and a Grand Prize fill-a-card game are also available for purchase. Weather related cancellations are possible.

    Event website ↗
  • 5pm

    Shadowverse Evolve Tournament

    Portals Games & Comics, 415 E Dover St, Easton · verified Sep 13
    See details

    This Shadowverse: Evolve tournament uses the standard format with best of one matches. Casual play takes place beforehand. Entry is $5 with prize support.

    Event website ↗
  • 6:30pm

    One Piece TCG Tournament

    Portals Games & Comics, 146 Kent Lndg, Stevensville · verified Sep 13
    See details

    This One Piece Trading Card Game tournament features single-game rounds in the Standard format. The entry fee is $5, and prizes are distributed as booster packs or store credit.

    Event website ↗
  • 7pm

    Weiss Schwarz Weekly Tournament

    Portals Games & Comics, 415 E Dover St, Easton · verified Sep 13
    See details

    Take part in a weekly Weiss Schwarz tournament featuring the Neo-Standard format. The event runs as a three-round Swiss, with best-of-one matches scheduled for 35 minutes each. Entry fee is $5. Arrive early to register and enjoy some casual games before the tournament begins.

    Event website ↗
  • 7pm

    Julian Velard

    The Avalon, 40 E Dover St, Easton · verified Sep 13
    See details

    Julian Velard pairs piano-forward songcraft with quick-witted humor, earning praise from The Guardian for the compelling pull of his melodies. A familiar face in the comedy world and a cult favorite in both the United States and Europe, he performs widely from his Los Angeles home base. His latest album, In the Middle of Something, unfolds as a reflective suite about the highs and lows of middle age and has also been adapted into a short musical film.

    Event website ↗
Sunday, September 27 3 events
  • 10am

    Beers & Gears Monthly Car Cruise

    Cult Classic Brewing, 1169 Shopping Center Rd, Stevensville · verified Sep 13
    See details

    A family-friendly monthly car cruise takes place at Cult Classic Brewing in the side parking lot. Enthusiasts can showcase or check out hot rods, muscle cars, classics, trucks, imports, bikes, and daily drivers. There are no trophies and no judging, creating a laid-back gathering focused on good cars and good company. Families and friends are welcome, and the event is open to everyone.

    Event website ↗
  • 11am

    RPG Day

    Portals Games & Comics, 146 Kent Lndg, Stevensville · verified Sep 13
    See details

    This weekly RPG gathering features volunteer Game Masters who host tables for up to six players. Arriving early is encouraged to introduce yourself, check for available seats, and find out what games are being run. Entry is $3. Sessions are open-table, but space can be limited, so checking availability ahead of time is recommended.

    Event website ↗
  • 1pm

    Resin and Crushed Glass Lantern Workshop

    Mallard Landing Community Clubhouse, 1134 Canvasback Ln, Denton · verified Sep 13
    See details

    Kristina Hoffmann from Salted Suds and Creations leads a hands-on UV resin and crushed glass lantern workshop for adults. Over two hours, participants learn how to craft a one-of-a-kind lantern using resin and crushed glass. All tools, materials, and step-by-step instruction are provided, and no prior resin experience is required. Everyone leaves with a finished piece. Capacity is limited to 24 participants. Attendees may bring a drink and a snack. Comfortable clothing is recommended, preferably something that can handle the possibility of a stain. Each lantern includes an LED RGB submersible light with a remote, and three AA batteries are provided.

    Event website ↗
Wednesday, September 30 2 events
  • 12am

    Chesapeake Bay & Maryland Eastern Shore Bike Tour

    Easton, MD, 127 S Locust Ln, Easton · verified Sep 13
    See details

    Spend four laid-back days savoring the food, history, and culture surrounding Maryland’s Chesapeake Bay while cycling the storied Eastern Shore. Gentle routes, waterfront vistas, fresh seafood, distinctive shops, and time in bayside towns dating to the 1600s set a relaxed rhythm with plenty to discover. Explore at your own pace with a SAG wagon close by, providing extra gear, cold drinks, and friendly encouragement whenever needed.

    Event website ↗
  • 1pm

    September Special Bingo

    210 Vincit St, Centreville · verified Sep 13
    See details

    Enjoy a special bingo session at the Active Aging Center. Reserve a spot with AAC staff, with $5 due at sign-up. That fee includes two bingo cards, and extra cards can be purchased in advance or on the day for $1 each. Only cash is accepted. Prize amounts grow as participation increases, and the activity may be canceled if there are not enough sign-ups. Volunteers are needed to call numbers, help with setup, and assist with check-in. Participation requires QAC Active Aging/Senior Center membership, and adults 55 and older can be members regardless of where they live. Lunch is available before the game with cream of tomato soup, gourmet chicken salad, copper pennies, hot cinnamon apples, and milk. For diners 60 and older, a $3 donation is suggested, and those ages 55 to 59 pay $6.79 for the meal.

    Event website ↗
Thursday, October 1 3 events
  • 8am

    2026 Eastern Shore Charity Golf Tournament

    Queenstown Harbor, 310 Links Lane, Queenstown · verified Sep 13
    See details

    This annual charity golf tournament supports the Rotary of Kent Island and United Way Queen Anne's County. Registration is followed by a shotgun start as sponsors and teams take to the course. Participation helps support nonprofit organizations in the local community.

    Event website ↗
  • 4pm

    RVFD's All You Can Eat Spaghetti Dinner

    Ridgely Volunteer Fire Department, 101 Sunset Blvd, Ridgely · verified Sep 13
    See details

    Enjoy a monthly all-you-can-eat spaghetti dinner for $11, complete with salad, garlic bread, dessert, and a drink. It offers a comfortable way to share a meal and catch up with friends and neighbors. Drive-thru pickup is also available, using the rear entrance and the open bay door.

    Event website ↗
  • 6:30pm

    1st Thursdays Karaoke

    Cult Classic Brewing Company, 1169 Shopping Center Rd, Stevensville · verified Sep 13
    Free

    First-Thursday karaoke brings a lively singalong vibe to Cult Classic Brewing Company as host Jimi keeps the mic circulating and the spotlight shared among performers. Admission is free, and early arrival is encouraged. The brewery offers a wide selection of house-brewed beers on tap along with fresh, from-scratch pizzas, hand-pattied burgers, jumbo wings and other pub fare for a full evening of music and fun.

    Event website ↗
Friday, October 2 4 events
  • 12pm

    Mid-Shore - Overnight Retreat

    Queen Anne's County 4-H Park, 100 Dulin Clark Rd, Centreville · verified Sep 13
    Free

    Enjoy a relaxed weekend retreat centered on simple camping and easygoing company. Arrive Friday and stay through Sunday. Tent camping in the park’s camping area is free. RV and camper spots are $50 per night and are available by reservation. There is no scheduled programming and no food or beer trucks... just time to unwind with like minded folks. Bring your RV or sleep under the stars, spread out with plenty of space, and make use of the bathhouse. Use the park as a base camp to explore the Shore or settle in and relax all weekend. An October chapter meeting will take place on Saturday afternoon, followed by a potluck dinner. Please bring a covered dish to share. No bonfires are permitted and animals must be kept on a leash. If you plan to stay both nights in an RV or camper, purchase a ticket for Friday and for Saturday. Contact Marianne for more information.

    Event website ↗
  • 5pm

    Easton's Fall Kickoff

    Downtown Easton, 11 S Harrison St, Easton · verified Sep 13
    Free

    Easton's Fall Kickoff brings shopping, dining, and a stroll along a path lined with giant pumpkins to downtown Easton. Local shops and galleries will be open to help you get ready for the season. Take your time browsing, enjoy a meal, and soak in the autumn atmosphere.

    Event website ↗
  • 6pm

    Pony Express Speed Show Series - 50 Year Celebration and Charity Event

    Queen Anne's County 4-H Fair, 106 Dulin Clark Rd, Centreville · verified Sep 13
    See details

    The Pony Express Speed Show Series marks 50 years with a charitable celebration featuring Speed Show #6 and five speed classes. Competitors can enter Barrels, Texas Barrels, Poles, and Plug, with one additional class to be announced. The fee is $20 per entry. Divisions are open to all ages, including lead line, junior, intermediate, senior, and adult, and points earned go toward year end high point awards. All competition follows 4-H Horse and Pony Rules, and the event supports the Queen Anne’s County Pony Express 4-H club.

    Event website ↗
Saturday, October 3 7 events
  • 9am

    *SAVE THE DATE * Town of Hurlock - 34th Annual Fall Festival 2026

    Welcome to Hurlock Maryland, 311 Charles St, Hurlock · verified Sep 13
    See details

    The Hurlock Fall Festival offers a full day of family-friendly activities, and Grandpa Rich's Jams, Jellies & Preserves will be back as part of the festivities. The day begins with a morning parade through town, then continues with scenic round-trip passenger train rides departing from the Hurlock Train Station. Around the station pavilion, visitors can browse local craft booths and flea market finds, enjoy plenty of food choices, and take in live music. Kids can look forward to pony rides, carriage rides, and hands-on activities, while entertainment and community displays add to the hometown spirit. Those interested in being a vendor can contact the Craft Vendor Coordinator at the Town of Hurlock. More details will be shared as the event approaches.

    Event website ↗
  • 11am

    ARToberfest

    Historic Stevensville, 105 Cockey Ln, Stevensville · verified Sep 13
    Free

    Historic Stevensville hosts a community celebration of creativity with ARToberfest, filling the Stevensville Arts & Entertainment District with live music, stage performances, and a marketplace of area artists and makers. Families can expect hands-on art projects for kids, games, and pumpkin decorating, along with plenty of tasty food. The event is free to attend and welcomes all ages. It highlights the season’s festive spirit and showcases local art and culture, presented in partnership with the Stevensville Arts & Entertainment District and supported by a QAC Outside Agency Grant.

    Event website ↗
  • 11am

    Alpaca Weekends at the Farm

    24480 Pinetown Rd, Preston · verified Sep 13
    See details

    On the first weekend of each month, Alpaca Weekends at the Farm welcomes visitors to roam open fields, meet alpacas up close, and take a guided tour of the farm. After exploring, stop into the shop for soft alpaca socks, lightweight sweaters, scarves, and other giftable items, then grab a bite from a local food truck. Each first weekend reflects the season, from spring babies to autumn farm scenes, so every visit offers something a little different. Suitable for families, friends, couples, or solo visitors. Tours are $10 per person.

    Event website ↗
  • 1pm

    Son's of the American Legion BBQ Chicken

    American Legion Caroline Post 29, 9238 Legion Rd, Denton · verified Sep 13
    See details

    At Caroline Post 29 in Denton, the Sons of the American Legion serve a barbecue chicken meal. The $12 plate includes barbecue chicken with beans, chips, and a roll. Meals are available until sold out.

    Event website ↗
  • 1pm

    The Met: Live in HD Così fan tutte

    The Avalon, 40 E Dover St, Easton · verified Sep 13
    See details

    The Met: Live in HD opens its season with Mozart’s Così fan tutte, a playful look at the whims of young love. Phelim McDermott’s production sets the story amid a 1950s Coney Island inspired boardwalk amusement park, where two couples face heart testing twists against a carnival backdrop. Soprano Federica Lombardi and mezzo-soprano Samantha Hankey sing Fiordiligi and Dorabella, with tenor Duke Kim and baritone Andrey Zhilikhovsky as Ferrando and Guglielmo. Bass-baritone Gerald Finley once again takes on Don Alfonso, and soprano Ana María Martínez appears as the maid Despina. The presentation runs about 3 hours and 57 minutes, includes one intermission, and is performed in Italian. A Live in HD season package offers eight operas for the price of seven, with senior and adult packages available online and student packages available by calling the box office. Individual tickets are priced at $23 for seniors, $25 for adults, and $15 for students, and children 8 and under are free, with fees additional. Jo Ann Kulesza, retired music director of Opera Programs at the Peabody Conservatory of Music, will be in the theater for a preview and discussion of the day’s opera, sharing extensive knowledge and firsthand experience.

    Event website ↗
  • 5pm

    CCC 2026 Monthly Cruise-In Nights

    Roberto's Pizza and Italian Restaurant, 8160 Elliott Rd, Easton · verified Sep 13
    See details

    Car enthusiasts gather for an easygoing cruise-in focused on cars and conversation. Hosted by Roberto's Pizza, this stop in the Cruisin' Cruise-Ins series moves to a new venue with a different menu each month. Every participant receives a 2025 Cruisin' Coin at each event, and collecting more coins increases the chances to win prizes throughout the season.

    Event website ↗
  • 7pm

    Release Concert @ Avalon

    The Avalon, 40 E Dover St, Easton · verified Sep 13
    See details

    Singer songwriter Kat Parsons takes the stage for a one night celebration of her new EP, The Sweetness Is Now. After a thirteen year gap since her last record, she returns with four new songs shaped by parenthood, love, loss, hope, and the sweetness that can be found even in difficult seasons. The set blends music from The Sweetness Is Now with audience favorites spanning more than two decades. The evening includes personal stories behind the songs, a few surprises, and appearances by special musical guests. Whether you have followed her work for years or are just discovering it, this concert marks a heartfelt new chapter.

    Event website ↗
Sunday, October 4 2 events
  • 10am

    Newby's Bowling Tournaments presents: The Eastern Shore Baker Trios Handicap Tournament

    Easton Bowling Center, 101 Marlboro Ave Ste 39, Easton · verified Sep 13
    See details

    Newby’s Bowling Tournaments brings a Baker Trios handicap event to the Eastern Shore at Easton Bowl. Teams compete for an estimated prize fund that, using 10 entries as a guide, pays $630 for first, $315 for second, and $225 for third, with final payouts adjusted by the number of entries. Entry is $210 per team, which covers $85 for lineage, $120 for the prize fund, and $5 in expenses. An $85 deposit reserves a spot and the remaining balance is due on the day of competition. Payment can be made by cash, check, PayPal, or Cash App, and checks should be made payable to Connor Newby. Online sign-up is available, and Newby’s Bowling Tournaments can provide details for completing payment electronically.

    Event website ↗
  • 11am

    Alpaca Weekends at the Farm

    Outstanding Dreams Alpaca Farm, 24480 Pinetown Rd, Preston · verified Sep 13
    See details

    Spend a few hours exploring the farm, strolling through open fields and meeting friendly alpacas. Guided tours of the farm offer plenty of up-close moments with the herd, followed by time to browse a store stocked with cozy alpaca socks, lightweight sweaters, scarves, gifts, and more. A local food truck is on site for convenient bites. Depending on the season, experiences vary, from spring babies to autumn farm vibes, so each visit feels a little different. This experience welcomes families, friends, couples, or solo visitors. Tours are $10 per person.

    Event website ↗
Tuesday, October 6 1 event
  • 11am

    October Book Club

    QAC Active Aging Center at the YMCA, 210 Vincit St, Centreville · verified Sep 13
    See details

    The book club will discuss Hamnet by Maggie O’Farrell, a historical novel set in plague-era England. The story follows a young Latin tutor living under a harsh father and his bond with Agnes, an unconventional healer known for her skill with plants who is often seen with a falcon. After they settle in Stratford-upon-Avon and her husband’s theater career grows in London, their family faces heartbreak when their young son dies of a sudden fever. Snacks and refreshments will be provided. No registration is required. Participants must be 55 or older and members of the QAC Senior Center or Active Aging Center. Membership is free.

    Event website ↗
Thursday, October 8 2 events
  • 10am

    Advance Healthcare Planning Assistance

    Talbot Hospice, 586 Cynwood Dr, Easton · verified Sep 13
    Free

    Talbot Hospice provides personalized guidance for advance healthcare planning, including help completing the Maryland Advance Directive or the Five Wishes form. Preparing in advance clarifies your preferences, reflects your values, and can ease decision-making for the people who care about you. Sessions are one-on-one and last 30 minutes. Participation is free and open to the public with an appointment. To schedule, call 410-822-6681 ext. 113.

    Event website ↗
  • 7pm

    The Del McCoury Band

    The Avalon, 40 E Dover Street, Easton · verified Sep 13
    See details

    Hall of Fame vocalist and guitarist Del McCoury brings bluegrass to life with a career that stretches from the genre’s early days to the present. From rough-and-ready honky-tonks and small-town school stages to the spotlight of the Grand Ole Opry, he has served as a bridge between the music’s roots and the digital era. Performing with The Del McCoury Band, a Grammy-winning ensemble, he pairs tradition with versatility. The group blends the signature high lonesome tone with modern agility, featuring his sons Ronnie on mandolin and Rob on banjo. Their accolades include multiple IBMA Entertainer of the Year awards and membership in the Grand Ole Opry since 2003, supported by more than three decades of steady, top-tier musicianship.

    Event website ↗
Saturday, October 10 5 events
  • 12pm

    6th Annual Fall Mystic Market

    Cult Classic Brewing, 1169 Shopping Center Rd, Stevensville · verified Sep 13
    See details

    The sixth annual Fall Mystic Market returns to Cult Classic Brewing with a focus on mystic and holistic interests. The event features many vendors, live music, and cocktails.

    Event website ↗
  • 12pm

    3rd Annual Boatyard Bash

    Richardson Maritime Museum, 103 Hayward St, Cambridge · verified Sep 13
    See details

    The 3rd Annual Boatyard Bash brings maritime heritage and live entertainment to the Richardson Maritime Museum. Enjoy performances by G Method and Chesapeake Sons, cheer on the Battle of the Boatyards Block Championship, explore displays of antique boats and classic cars, take boatworks tours, and find family activities alongside craft vendors with plenty of food and drinks. Admission is $20 for adults, $10 for ages 13 to 20, and free for children 12 and under.

    Event website ↗
  • 3pm

    Read with Harriet

    Harriet Tubman Museum and Educational Center, 424 Race St, Cambridge · verified Sep 13
    See details

    The first Read with Harriet Book Club centers on a discussion of Combee by Edda Fields-Black. The reading list also features Sailing to Freedom by Timothy D. Walker and Frederick Douglass by David Blight. RSVP information will be posted on the website.

    Event website ↗
  • 7pm

    Music Heals: A Benefit Concert

    Cult Classic Brewing Company, 1169 Shopping Center Rd, Stevensville · verified Sep 13
    See details

    Music Heals is a benefit concert dedicated to supporting EBeauty Community as it serves women at the beginning of their cancer journey. The evening features performances by legendary guitar maker and musician Paul Reed Smith with his EIGHTLOCK band, along with special guests The Stringtown Band. Guests can look forward to an intimate concert setting, auctions and raffles, and great food and drinks, all focused on advancing free appearance related support that helps people facing cancer regain confidence, dignity, and hope. This event arrives at a pivotal time, as EBeauty has been entrusted with more than 100,000 wigs, mastectomy bras, breast forms, and other appearance related resources, opening the door to expand assistance to thousands more individuals in treatment across the country. Whether you are a music fan, survivor, healthcare professional, or advocate, the power of live music comes together here to make a meaningful difference.

    Event website ↗
  • 7pm

    The Jersey Tenors

    The Avalon, 40 E Dover Street, Easton · verified Sep 13
    See details

    The Jersey Tenors bring a high energy fusion of opera and rock to The Avalon, showcasing top tier vocals praised by The Observer. The set moves from timeless arias to hits by Queen, Elton John, and Bon Jovi, all delivered with rich harmonies and big-stage flair. True to their New Jersey roots, they spotlight homegrown legends including Frankie Valli and The Four Seasons, Frank Sinatra, Bruce Springsteen, Kool and the Gang, and Whitney Houston. Expect powerhouse vocals and plenty of chances to sing along. Tickets are $45, fees not included.

    Event website ↗
Sunday, October 11 1 event
  • 11am

    Fall Fest 10/11 11-3pm

    A Little Farm and Nursery, 100 Davidson Dr, Stevensville · verified Sep 13
    See details

    A festive autumn gathering featuring pumpkins, a maze to explore, a variety of games, and more seasonal activities.

    Event website ↗
Tuesday, October 13 2 events
  • 1pm

    Caregiver's Support Group

    Queen Anne's County Family YMCA and Active Aging Center, 210 Vincit St, Centreville · verified Sep 13
    See details

    Caregivers gather in a supportive setting to discuss physical and cognitive challenges, learn about early warning signs, and encourage one another. Sessions frequently feature guest speakers and a fresh topic each month, offering practical insights and shared understanding throughout the caregiving journey.

    Event website ↗
  • 6pm

    Books & Beers 2026

    Cult Classic Brewing, 1169 Shopping Center Rd, Stevensville · verified Sep 13
    Free

    This meetup takes place at Cult Classic Brewing, where attendees begin with conversation and questions about the selection, then finish by imagining a cast for a film or miniseries over beverages. This session focuses on Carrie by Steven King. There is no cost to attend, and anyone who has completed the book is welcome. Participants do not need to be 21. Suggestions for next year’s reading list are encouraged. Copies can be found through Brackish Books at the Kent Island Farmers Market or borrowed from local libraries.

    Event website ↗
Wednesday, October 14 2 events
  • 12pm

    Caregiver Support Group at SNBH

    Shore Neurocognitive Health, 29466 Pintail Dr, Easton · verified Sep 13
    See details

    Caregiving can be deeply fulfilling yet at times overwhelming. The Caregiver Support Group at SNBH provides a warm, supportive setting where participants can share experiences, connect with others facing similar challenges, and find encouragement. Meeting monthly, it offers a chance to recharge and draw strength from a community that understands.

    Event website ↗
  • 5pm

    Wednesday Wing Night at the American legion

    9238 Legion Rd, Denton · verified Sep 13
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    Caroline Post 29 hosts Wing Night with a range of flavors to choose from. Pricing options include 6 wings for $5 or a dozen for $10.

    Event website ↗
Thursday, October 15 1 event
  • 7pm

    Scary Stories at Cult Classic

    Cult Classic Brewing, 1169 Shopping Center Rd, Stevensville · verified Sep 13
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    Local authors take the stage at Cult Classic Brewing to share short, spine-tingling stories in a live reading showcase. Each writer presents a three to five minute tale crafted to deliver quick chills and lingering goosebumps. Reserved seating is available for $5. The taproom offers a wide range of house-brewed beers along with fresh pizzas made from scratch, hand-formed burgers, jumbo wings, and other pub favorites, so arriving early makes it easy to settle in with food and a drink. Guests who need accessibility or other accommodations can speak with staff at the door. Any unclaimed tickets near showtime may be released to a standby line. Events here are generally all ages unless noted otherwise, and dogs are welcome on the patio but not inside. All sales are final, with refunds or exchanges only if the show is canceled, and supporting acts or set times may change.

    Event website ↗
Friday, October 16 1 event
  • 5:30pm

    Variety Prize Bingo

    Ruthsburg Community Center, Queen Anne · verified Sep 13
    See details

    Take part in a bingo event with 15 games, along with specials and raffles. Advance tickets cost $25, while admission at the door is $30. Seats can be reserved in advance.

    Event website ↗
Saturday, October 17 3 events
  • 8am

    HALLMARK ORNAMENT DEBUT

    Edwards Pharmacy, 102 S Commerce St, Centreville · verified Sep 13
    See details

    The Ornament Debut at a Hallmark Gold Crown store showcases exclusive Hallmark ornaments. Explore a selection of over 300 new ornaments.

    Event website ↗
  • 1pm

    The Met: Live in HD Macbeth by Giuseppe Verdi

    The Avalon, 40 E Dover St, Easton · verified Sep 13
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    At The Avalon, The Met: Live in HD presents a new production of Giuseppe Verdi’s Macbeth, inspired by Shakespeare’s tragedy of fierce ambition and its consequences. Baritone Quinn Kelsey appears as the troubled Scottish ruler, with soprano Lise Davidsen as Lady Macbeth. The cast also includes tenor Freddie De Tommaso as Macduff and bass-baritone Ryan Speedo Green as Banquo. Met Music Director Yannick Nézet-Séguin conducts, and the staging is by Louisa Proske. The performance is sung in Italian and runs about 3 hours and 29 minutes, with one intermission. Tickets are available with senior, adult, and student pricing, and children 8 and under attend free, with fees additional. A Met: Live in HD package offers eight operas for the price of seven. Senior and adult packages are available online, and student packages can be arranged by calling the box office. A preview and discussion of the opera with Jo Ann Kulesza, retired Music Director of Opera Programs at the Peabody Conservatory of Music, will take place in the theatre.

    Event website ↗
  • 1:30pm

    Veterans' Benefit: Connecting with your Loved Ones with Medium Debbie

    Kent Island American Legion Post 278, 800 Romancoke Rd, Stevensville · verified Sep 13
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    At Kent Island American Legion Post 278, Medium Debbie leads a live mediumship program in support of veterans. Hosted by the Kent Island American Legion Auxiliary, the experience features messages for randomly selected attendees from loved ones in spirit. Not everyone will receive a reading, but guests can learn more about how spirit communication works. Proceeds benefit programs serving veterans, including MCVET, which offers comprehensive services to homeless and other veterans in need to help them successfully reenter their communities. All profits are donated to the American Legion Auxiliary to advance these efforts. Admission is $45 per person and includes generous snacks, with a cash bar available. Attendees must be 18 years of age.

    Event website ↗
Sunday, October 18 1 event
  • 9:30am

    St Michaels Jack Russell Races

    St Michaels Inn, 1228 S Talbot St, Saint Michaels · verified Sep 13
    See details

    Celebrate a playful day for dogs and their people with spirited dog races. Owners can register their pups to take part, and participation is open to dogs of every kind. You can also show support by purchasing a bone sign that helps this event and its partners. For more details and updates, watch for posts on Facebook.

    Event website ↗
Tuesday, October 20 2 events
  • 11am

    Puzzle and Book Swap

    QAC Active Aging Center at the YMCA, 210 Vincit St, Centreville · verified Sep 13
    Free

    Enjoy a no-cost swap of puzzles and books with fellow members. Bring complete puzzles and books to exchange, then choose options that are new to you. Any remaining items at the end will be available on a first come, first served basis. Please do not bring puzzles with missing pieces. You may take items without bringing any, however storage space is limited, so donations cannot be accepted. If you plan to bring items, please plan to take items as well. Participation is limited to QAC Active Aging/Senior Center members.

    Event website ↗
  • 11:30am

    Lunch & Learn

    The Narrows Restaurant, 3023 Kent Narrow Way S, Grasonville · verified Sep 13
    Free

    Enjoy a free lunch or dinner while exploring thoughtful ways to honor a loved one at The Narrows Restaurant. This educational session explains how planning ahead can bring peace of mind and may lessen the financial and emotional burden on family members. Ryan Helfenbein, a partner with Fellows, Helfenbein & Newnam Funeral Home and Lasting Tributes and a regular columnist for Outlook by the Bay, leads the presentation. Conversation points include eco conscious burial choices, veterans benefits, creating a personal celebration of life, and options for preplanning and paying in advance, with time for candid questions. Space is limited, and the setting is comfortable and welcoming.

    Event website ↗
Thursday, October 22 1 event
  • 4pm

    Fourth Annual CMS Fall Thing Festival

    Centreville Middle School, 231 Ruthsburg Rd, Centreville · verified Sep 13
    See details

    The Fourth Annual CMS Fall Thing Festival features a variety of attractions. Attendees will find food trucks, displays of emergency equipment, booths hosted by community groups, craft and artisan vendors, games and activities, live music, special appearances, and a car show, with more to discover.

    Event website ↗
Saturday, October 24 2 events
  • 10am

    Fall Fest 10/24 10-3pm

    100 Davidson Dr, Stevensville · verified Sep 13
    See details

    This fall festival highlights pumpkin fun, a maze to wander, games to play, and other seasonal activities, offering a simple way to enjoy autumn.

    Event website ↗
  • 12pm

    Queer Dungeons & Dragons

    7401 Ocean Gtwy, Easton · verified Sep 13
    See details

    Step into a Dungeons & Dragons adventure where you can be whoever you want to be. Create a hero and team up with fellow players to traverse a magical realm, face obstacles, and battle monsters and villains. A local Dungeon Master leads the game. No experience or materials are required. Bring a Level 7 character or choose from pre-made options, and play using 5th edition D&D.

    Event website ↗
Sunday, October 25 2 events
  • 10am

    ESSM- Beers & Gears Monthly Car Cruise!!

    Cult Classic Brewing, 1169 Shopping Center Rd, Stevensville · verified Sep 13
    See details

    An all-ages monthly car cruise at Cult Classic Brewing welcomes every kind of vehicle, from hot rods and muscle cars to classics, trucks, imports, bikes, and daily drivers. There are no awards or judging, just a relaxed get-together focused on the cars and the people who love them. Everyone is welcome, with vehicles gathering in the brewery’s side parking lot.

    Event website ↗
  • 11am

    Fall Fest 10/25 11-3pm

    100 Davidson Dr, Stevensville · verified Sep 13
    See details

    Celebrate fall with pumpkins, a maze, games, and more.

    Event website ↗
Thursday, October 29 1 event
  • 7pm

    Stillhouse Junkies

    The Avalon, 40 E Dover Street, Easton · verified Sep 13
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    At The Avalon, Colorado-based trio Stillhouse Junkies showcases a high-energy acoustic sound that moves between roots, bluegrass, Texas swing, blues, and rock. Founder Fred Kosak plays guitar and mandolin alongside Alissa Wolf on fiddle and Jeanette Adams on upright bass, and their free-flowing interplay and improvisation make each performance distinct. Expect intricately crafted original songs and an adventurous approach without retracing the same route twice. Becky Buller of The Becky Buller Band has praised their big, joyful sound, deft picking, and strong songwriting, and the group continues to build a reputation across the acoustic music scene in the United States and abroad.

    Event website ↗
Tuesday, November 3 1 event
  • 11am

    November Book Club

    210 Vincit St, Centreville · verified Sep 13
    See details

    Readers will meet to discuss The Cats Came Back by Sofia Kelly. Set in Mayville Heights, Minnesota during a lively music festival, the book follows Kathleen and her cats, Owen and Hercules, after they discover a body by the river. The victim is the close friend of a cabaret singer scheduled to perform and looks strikingly similar to her, which raises the possibility of mistaken identity. With rumors swirling, the trio relies on both everyday and unusual skills to uncover the truth. Snacks and refreshments are provided. No registration is required. Participants must be 55 or older and members of the QAC Senior Center or Active Aging Center. Membership is free.

    Event website ↗
Thursday, November 5 1 event
  • 7pm

    Jake Shimabukuro

    The Avalon, 40 E Dover Street, Easton · verified Sep 13
    See details

    Internationally acclaimed ukulele virtuoso Jake Shimabukuro brings his trailblazing musicianship to The Avalon, showcasing the dazzling technique and heartfelt touch that have helped reinvent what the instrument can do today. Frequently compared to Jimi Hendrix for his fearless creativity, he blends jazz, rock, classical, blues, folk, and the sounds of his Hawaiian roots into a dynamic performance. Over a prolific career of celebrated recordings, he has collaborated with renowned artists including Bette Midler, Yo-Yo Ma, Jimmy Buffett, Ziggy Marley, and Mick Fleetwood, and has appeared on legendary stages such as the Sydney Opera House, the Hollywood Bowl, and the Kennedy Center. Tickets cost $50, plus fees.

    Event website ↗
Saturday, November 7 4 events
  • 8am

    Mispillion Kennel Club - Rally & Obedience Trials

    Talbot Kennel Club, 405 W Bell Rd Unit 6, Ridgely · verified Sep 13
    See details

    Presented by Mispillion Kennel Club at Talbot Kennel Club, this event showcases canine rally and obedience trials, highlighting the partnership between dogs and handlers through structured courses and exercises in a formal trial setting.

    Event website ↗
  • 9am

    Easton Gun Show

    Easton Volunteer Fire Dept. MD, 315 Leonard Rieck Dr, Easton · verified Sep 13
    See details

    This event is a gun show at the Easton Volunteer Fire Dept. Admission is $8, and vendor tables are available for $60.

    Event website ↗
  • 9:30am

    9th Annual Mid-Shore S.T.E.M Festival Imagination & Innovation

    8230 Detour Rd, Denton · verified Sep 13
    Free

    The ninth annual Mid-Shore S.T.E.M. Festival celebrates imagination and innovation with a free event at Caroline County 4-H Park, open to youth of all ages. Participants can explore hands-on activities, interactive exhibits, and demonstrations that connect curiosity with real-world science. Career connections are part of the experience, and a special emphasis on artificial intelligence and other emerging technologies highlights how STEM influences everyday life. Areas of interest such as robotics, coding, engineering, agriculture, healthcare, and environmental science are featured, offering many ways to dive in and discover how things work.

    Event website ↗
  • 11am

    Alpaca Weekends at the Farm

    24480 Pinetown Rd, Preston · verified Sep 13
    See details

    Guests can explore an alpaca farm on guided tours that provide close-up time with the herd, expansive fields to roam, and fresh countryside air. The shop features alpaca socks, lightweight sweaters, scarves, gifts, and other finds, and a local food truck provides convenient meal options on site. Seasonal highlights, from spring newborns to an autumn farm atmosphere, make each visit feel a little different. Suitable for families, friends, or a casual date. Tours are $10 per person.

    Event website ↗
Sunday, November 8 2 events
  • 9am

    American Legion Jeff Davis Post 18 6th Annual Lewis Class Shoot!

    509 Pintail Point Farm Ln, Queenstown · verified Sep 13
    See details

    American Legion Jeff Davis Post 18 presents the 6th Annual Lewis Class Shoot at The Point at Pintail. Participants can take part in a 50-target shoot across three divisions, with trophies, lunch provided, and optional cash side games. More than $2,000 in cash and prizes will be awarded. Entry fees are $100 per individual or $375 for a four-person team. Additional details and a registration form are available on the organization’s website.

    Event website ↗
  • 11am

    Alpaca Weekends at the Farm

    24480 Pinetown Rd, Preston · verified Sep 13
    See details

    Enjoy a relaxed day at the farm with friendly alpacas, fresh country air, and a guided look behind the scenes. Wander open fields, meet the herd up close, and learn about daily life on the property during a tour. Browse the farm store for cozy alpaca socks, lightweight sweaters, scarves, and distinctive gifts you will not find just anywhere. A local food truck will be on site for convenient bites between activities. Each visit brings its own seasonal touches, from new spring arrivals to autumn farm vibes, so the experience feels a little different every time. Tours last one hour and cost $10 per person, and the outing suits families, friends, couples, and solo visitors alike.

    Event website ↗
Tuesday, November 10 1 event
  • 11:30am

    Lunch & Learn

    Olive Garden (Easton - Maryland), 9017 Ocean Gtwy, Easton · verified Sep 13
    Free

    Enjoy a complimentary lunch or dinner while learning caring and practical ways to honor a loved one. This educational program explains how planning in advance can ease stress, offer peace of mind, and potentially save families thousands. Space is limited. The session is led by Ryan Helfenbein, a partner with Fellows, Helfenbein & Newnam Funeral Home and Lasting Tributes and a columnist for Outlook by the Bay. Topics include green burial options, veteran’s benefits, creating a meaningful celebration of life, and preplanning and prepayment choices, and the presentation provides clear answers to difficult questions in a comfortable, welcoming setting.

    Event website ↗
Friday, November 13 3 events
  • 10am

    55th Annual Waterfowl Festival

    28 S Harrison St, Easton · verified Sep 13
    See details

    The 55th Annual Waterfowl Festival is a three-day celebration of Eastern Shore arts and culture. It funds conservation and education, continuing a commitment that began in 1971.

    Event website ↗
  • 10am

    Dutchman's Chainsaw Challenge 2026

    Tractor Supply - 29328 Cecil Dr Easton MD 21601, 29328 Cecil Dr, Easton · verified Sep 13
    See details

    Dutchman's Chainsaw Challenge brings together Professional and Master level chainsaw carvers from the Eastern United States to compete for top prizes and the Dutchman's Chainsaw Challenge title. Taking place at Tractor Supply, the site hums with saws and the scent of fresh-cut wood as artists transform logs into striking sculptures in real time. Highlighted as part of the Waterfowl Festival, it showcases impressive craftsmanship and live carving in a vibrant, art-forward setting. Proceeds support the artists and Chesapeake Creative Wellness of Easton, which uses music and the creative arts to help adults living with PTSD and anxiety, while building awareness and reducing stigma for veterans, survivors of violence, first responders, medical staff, and others.

    Event website ↗
  • 11am

    Chesapeake Mermaid at the Waterfowl Festival

    Talbot County Free Library, 100 W Dover St, Easton · verified Sep 13
    See details

    At the Waterfowl Festival, the Chesapeake Mermaid presents a lively program of stories, music, and movement that celebrates the Chesapeake Bay. Audience members of all ages can meet her wildlife friends, learn simple sign language inspired by bay creatures, and take part in an interactive storytime that sparks curiosity and imagination. After the program, families can enjoy Mermaid Moments for personal interactions and photos. Performances are hosted at Talbot County Free Library, with themed sessions that include The Last Bivalvian, Giants of the Bay, and Century Island. Attendees can also pick up storybooks and activity books to continue the adventure at home. For over 50 years, this annual festival has generated $5.7 million for wildlife and habitat conservation, education, and research, welcoming more than 20,000 visitors to celebrate local wildlife, nature, art, heritage, food, and fun.

    Event website ↗
Tuesday, November 17 1 event
  • 11:30am

    Lunch & Learn

    Fisherman's Inn, 3116 Main St, Grasonville · verified Sep 13
    Free

    Enjoy a complimentary meal while exploring thoughtful ways to honor a loved one at Fisherman's Inn. Led by Ryan Helfenbein, a partner with Fellows, Helfenbein & Newnam Funeral Home and Lasting Tributes and a columnist for Outlook by the Bay, this session explains the benefits of planning in advance, how doing so can bring peace of mind, and ways it may help reduce expenses for families. Topics include eco friendly burial options, veterans benefits, creating a personalized celebration of life, and choices for preplanning and prepayment, with clear answers to even the toughest questions in a comfortable, welcoming setting. Seating is limited.

    Event website ↗
Wednesday, November 18 1 event
  • 1pm

    Novmber Special Bingo

    210 Vincit St, Centreville · verified Sep 13
    See details

    Enjoy a special bingo session for members of the QAC Active Aging/Senior Center. Sign-up is required with AAC staff, and a $5 fee is due at registration. The fee includes two bingo cards, and extra cards can be purchased in advance or on the day for $1 each. Cash is the only accepted form of payment. The prize pool increases with attendance, so bringing friends can boost the winnings. Anyone 55 or older can become a member, regardless of residence. This activity may be canceled if there are not enough participants. Lunch is available before the games. For those 60 and older, a $3 contribution is suggested for the meal, while participants ages 55 to 59 pay $6.79. Volunteers are needed to call numbers, assist with setup, and help with check-in. Participation is limited to current QAC Active Aging/Senior Center members.

    Event website ↗
Friday, November 20 1 event
  • 10am

    Cabin Fever Play Centre

    Cabin Fever Play Centre, 442 Race Street, Cambridge · verified Sep 13
    See details

    Cabin Fever Play Centre hosts a morning of active fun for homeschool families. The indoor facility offers plenty to explore, including multi-level play structures for climbing and sliding, a ball blaster arena for friendly challenges, a sensory room, and an arcade. Families may bring packed lunches and stay to eat together after the play session, or purchase food from the on-site concession. Everyone entering the play areas must wear socks, and each participant needs a signed waiver. The cost is $10 per child, with payment taken on site. Advance sign-up is requested to help with a head count. For questions, contact Amy Young with Region 6 Dorchester and Talbot Counties at amy.young@paxacademy.org or 443-205-2987.

    Event website ↗
Sunday, November 22 1 event
  • 12pm

    Turkey Trot and Inflatable Race

    100 Davidson Dr, Stevensville · verified Sep 13
    See details

    A children’s obstacle course takes center stage, and an inflatable race is being included for the first time this year.

    Event website ↗
Friday, November 27 1 event
  • 9pm

    The Agitators at Carpenter St. Saloon

    Carpenter Street Saloon, 111 S Talbot St, St Michaels · verified Sep 13
    See details

    Pete Baker & The Agitators return to St. Michaels for a rowdy night of straight-ahead rock and roll at Carpenter Street Saloon. It is their only St. Michaels appearance this year.

    Event website ↗
Saturday, November 28 2 events
  • 10am

    Shop Small Saturday

    11 S Harrison St, Easton · verified Sep 13
    See details

    Kick off the holiday season with Shop Small Saturday by backing neighborhood merchants. Celebrate your community and the spirit of the season by choosing to shop local.

    Event website ↗
  • 7pm

    Disciple of the Garden LIVE at Cult

    Cult Classic Brewing, 1169 Shopping Center Rd, Stevensville · verified Sep 13
    See details

    Disciple of the Garden brings a devoted Chris Cornell tribute to Cult Classic Brewing, celebrating his enduring influence through the power and emotion of the songs he made famous. The band performs favorites from Soundgarden, Audioslave, Temple of the Dog, and his solo catalog, balancing recognizable hits with select deep cuts. Led by guitarist and vocalist Joe Leo and based in Westchester County, New York, D.O.G. focuses on the soaring vocals, heartfelt lyrics, and intensity that defined Cornell’s work, aiming to capture the energy and spirit of his performances. General admission is $20 in advance or $25 at the door. Reserved high seating is $35 per person in advance. Cult Classic Brewing features more than 15 house-brewed beers, a full kitchen serving from-scratch pizza, hand-pattied burgers, and fresh, never frozen jumbo wings, plus a full bar. Shows at this venue are all ages unless otherwise noted. Guests who need accessibility or special accommodations can speak with staff at the door. Dogs are welcome on the patio but not inside the building.

    Event website ↗
Sunday, November 29 1 event
  • 10am

    ESSM- Beers & Gears Monthly Car Cruise!!

    Cult Classic Brewing, 1169 Shopping Center Rd, Stevensville · verified Sep 13
    See details

    Enjoy a family-friendly monthly car cruise that welcomes every kind of ride, including hot rods, muscle cars, classics, trucks, imports, bikes, and daily drivers. There are no awards or judging, creating a relaxed setting centered on the vehicles and the community. The gathering takes place at Cult Classic brewery on Kent Island in the side parking lot, and it is open to everyone.

    Event website ↗
Tuesday, December 1 1 event
  • 11am

    December Book Club

    210 Vincit St, Centreville · verified Sep 13
    See details

    Readers gather for a discussion of Verity by Colleen Hoover. The story follows Lowen Ashleigh, a novelist in financial trouble who accepts a job from Jeremy Crawford to finish his injured wife Verity’s hit series. While sorting through Verity’s papers, Lowen finds a hidden, unfinished autobiography filled with unsettling confessions, including an account of a tragic night that changed the family. Keeping the manuscript secret from Jeremy grows complicated as Lowen’s feelings for him deepen, and she weighs the consequences of revealing a truth that could upend his devotion to his wife. Refreshments and snacks are provided. No registration is required. Participants must be 55 or older and members of the QAC Senior Center or Active Aging Center. Membership is free.

    Event website ↗
Friday, December 4 1 event
  • 7pm

    Medium Debbie Wojciechowski

    The Avalon, 40 E Dover St, Easton · verified Sep 13
    See details

    Medium Debbie Wojciechowski returns to the Stoltz to share messages from loved ones who have passed, offering thoughtful readings in an intimate setting. She grew up in Baltimore and considers herself an ordinary person with an uncommon gift to connect with the other side. Her background in federal law enforcement, paired with her mediumship, has led her to consult on cold cases and missing person investigations. Drawing on professional experience in mental health and grief counseling, she approaches sensitive readings with care and compassion. She views this work with humility and a strong sense of responsibility. For seating logistics, Tables A and B will be on the stage, which is reached by two steps, to help her move through the room more easily.

    Event website ↗
Saturday, December 5 3 events
  • 12pm

    The Met: Live in HD Samson et Dalila by Camille Saint-Saëns

    The Avalon, 40 E Dover Street, Easton · verified Sep 13
    See details

    At The Avalon, The Met: Live in HD presents Camille Saint-Saëns’s Samson et Dalila in a revival of the company’s grand staging. The story of the powerful biblical figure and the alluring Philistine is realized with full orchestra and chorus and music that leaves a strong impression. Giacomo Sagripanti conducts, with mezzo-soprano Aigul Akhmetshina and tenor Clay Hilley leading the cast. The screening runs 3 hours and 54 minutes, includes two intermissions, and is sung in French. Tickets are Senior $23, Adult $25, Student $15, and children 8 and under are admitted free, with fees additional. A Met: Live in HD package is available offering 8 operas for the price of 7, with senior and adult packages available online and student packages available through the box office. A pre-show preview and discussion is planned with Jo Ann Kulesza, retired Music Director of Opera Programs at the Peabody Conservatory of Music, who shares insights drawn from years of study and first-hand experience with the art form and the expressive power of the human voice.

    Event website ↗
  • 6:30pm

    Easton's Holiday Parade

    11 S Harrison St, Easton · verified Sep 13
    Free

    Easton’s holiday parade brings seasonal spirit to the community, featuring a wide mix of decorated vehicles, creative novelties, and colorful floats that highlight Easton's best during the holiday season. Before the procession begins, Santa arrives in Thompson Park, followed by a festive tree lighting. Street closures along the route will be in place ahead of the start.

    Event website ↗
  • 7pm

    12.5.26 Connecting with Your Loved Ones at The Avalon Theater

    The Avalon, 40 E Dover St, Easton · verified Sep 13
    See details

    Medium Debbie Wojciechowski returns to the Avalon Theatre’s Stoltz Listening Room in Easton, Maryland for an intimate evening of evidential mediumship. Born and raised in Baltimore, she describes herself as an ordinary person with the uncommon ability to connect with loved ones who have passed. During the event, she will share messages with randomly selected attendees, offering details meant to affirm enduring bonds beyond death. Not everyone will receive a personal reading, though all attendees can expect a window into the practice of mediumship. With a background in federal law enforcement and professional experience in mental health and grief counseling, Debbie approaches her work with a steady, compassionate, and respectful presence and treats the responsibility with care. Tickets are $50, with additional fees. Please note that Table A and Table B will be placed on the stage, and guests seated there will need to walk up two steps to allow Debbie to move through the room more easily.

    Event website ↗
Sunday, December 6 2 events
  • 8am

    Stocking Suffer 8-hr Endurance Run

    Terrapin Nature Area, 191 Log Canoe Cir, Stevensville · verified Sep 13
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    Spend a day circling a 2.8 mile loop at Terrapin Nature Area during an 8 hour endurance run where participants choose their own pace and distance. The route moves counterclockwise, includes a brief stretch of soft sand on each lap, and starts and finishes in front of the Ranger’s office. After every lap, runners check in with the lap counter so results and rewards can be tracked. Each participant receives a stocking, and a new surprise is added to it with every completed circuit. At the end of the event, runners take home everything they have collected along with a special check out gift. The top male and female with the most laps earn awards. Support along the way includes a well supplied aid station at the start and finish offering water, sports drink, and a variety of snacks. There is ample space to set up a personal rest or aid area, and facilities include full service restrooms near the start and finish plus several porta potties on the course. The event welcomes friendly competition as well as personal challenges and a spirit of camaraderie. Registration is limited to 100 participants. This run also supports local causes. Participants are asked to bring an unwrapped toy for Toys for Tots, and cash donations will benefit Haven Ministries Emergency Food Bank. Haven Ministries operates two food pantries configured like grocery stores so clients can select what they need, with food provided through community donations and purchases through the Maryland Food Bank. Sponsorships from local businesses and organizations are invited to help make a positive impact for children and families through these charities. Presented by Kent Island Running Group, a 501(c)(3) nonprofit that promotes active living while partnering with local organizations for community benefit.

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  • 11am

    Tide & Tinsel - A Tilghman Island Christmas Market

    Tilghman Island Volunteer Fire Company, 5979 Tilghman Island Rd, Tilghman Island · verified Sep 13
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    Tide & Tinsel brings a cheerful Christmas market to Tilghman Island, showcasing the work of local artists, makers, and small businesses. Browse handcrafted gifts, coastal themed creations, and distinctive finds that celebrate the island’s creativity. Hosted at the Tilghman Island Fire Hall, the market complements the community’s seasonal celebrations and adds extra sparkle to the holidays. It offers a warm way to support local vendors, discover meaningful presents, and enjoy the spirit of Christmas in true island fashion.

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Thursday, December 10 1 event
  • 8pm

    Mid-Shore Side of Beef Fundraiser 2026

    Easton VFW, 223 Glebe Rd, Easton · verified Sep 13
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    Support the Mid-Shore chapter with a fundraiser that offers a chance to win a side of beef along with a 9 CF chest freezer. If the beef and freezer are not your preference, a $1,000 cash prize is available instead. A limited number of tickets are available online, and in person sales are handled by chapter members. Single tickets are $10 each, and every ticket equals one entry. Discounted trifecta bundles are priced at 3 for $25, and you can purchase them in multiples of three, for example four trifecta bundles provide 12 entries for $100. The drawing will be held during a chapter meeting, and you do not need to be present to win. The side of beef will be available for pickup at QCF Angus Ranch in Queen Anne, MD after the drawing once a side is ready from the butcher, and pickup times will be coordinated directly with the ranch.

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Friday, December 11 1 event
  • 5pm

    Christmas in St. Michaels, Maryland | Enjoy our historic waterfront town!

    St. Michaels Historic District, 114 S Talbot St, St Michaels · verified Sep 13
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    Historic waterfront St. Michaels, Maryland, comes alive with a weekend of Christmas festivities in the St. Michaels Historic District. Enjoy holiday shopping across town, lively parades by day and after dark, a tour of homes, festive meals, activities for children, and many other seasonal highlights. This volunteer-led celebration has, with the support of sponsors and patrons over the years, raised more than $1.7 million to benefit local children and adults through family-focused services, education and child development, and community enhancement programs. Please be cautious of scams. The organizers do not solicit vendor opportunities, and most activities do not require tickets. If tickets are needed, purchase only through the official website, where updates and ornament sales are also available.

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