Events in Chester, NY

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

18This week
60Next 30 days
1Free this week
50Venues tracked

This weekend in Chester

The ones worth planning around. All 10 weekend events →

Trustee Time

Sat, Sep 19 · 8:30am · Java Blue Coffee & Market, Montgomery

Live music in Chester

5 shows this weeksee the full live-music calendar →

  • Sat 1pm

    Jersey Swamp Cats at Wright Family Farm

    Wright Family Farm, 335 Kings Hwy, Warwick · verified Sep 13
    See details

    Ride a hayride to the concert stage at Wright Family Farm for the Jersey Swamp Cats’ debut at the venue. The band will deliver jump blues, New Orleans rhythm and blues, and vintage rock and roll, highlighted by their signature back-and-forth between guitar and piano.

    Event website ↗
  • Sat 6:30pm

    The Beatles Candlelight Experience In Newburgh, NY - Saturday September 19th

    Christ Lutheran Church Newburgh, NY, 186 Fullerton Ave, Newburgh · verified Sep 13
    See details

    Presented by Lumos, this classical tribute to The Beatles takes place at Christ Lutheran Church in Newburgh. A string trio performs songs including Come Together, Here Comes the Sun, Eleanor Rigby, Yesterday, Twist and Shout, Good Day Sunshine, Lady Madonna, Blackbird, Get Back, Let It Be, Penny Lane, All You Need Is Love, Something, Yellow Submarine, Help, and Hey Jude. Two sittings are offered. Seating is first come, first served within your chosen tiered zone, available in Platinum, Gold, Silver, or Bronze. The venue is wheelchair accessible, though front row placement cannot be guaranteed. This event is for ages eight and older. Lumos partners with churches and venues across the United States and makes a donation to a different charity each month.

    Event website ↗
  • Sat 8pm

    Moonflower Classic Rock @ The Union House Inn

    22 Hepper St, Walden · verified Sep 13
    See details

    Moonflower takes the stage at The Union House Inn for a debut performance filled with classic rock favorites and timeless anthems. Enjoy live music alongside great food and ice cold drinks, with plenty of chances for dancing and sing along moments. There is no cover charge.

    Event website ↗
  • Wed 2pm

    Lunch & A Show

    Sugar Loaf Performing Arts Center Pavilion, 233 Creamery Pond Rd, Chester · verified Sep 13
    See details

    Experience a relaxed meal paired with a live performance at Sugar Loaf Performing Arts Center Pavilion. The Acchords, featuring Tommy, Warren, Joe, and Dennis, bring tight harmonies and high energy as they move from timeless favorites to contemporary tunes across a variety of genres. The price is $65 per person and includes lunch and the show. Food is by Graze & Ice Capps, with menu details to be announced.

    Event website ↗

All upcoming events, day by day

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

Thursday, September 17 1 event
  • 4pm

    Ribbon Cutting: Mackey Catania & Whalen LLP

    103 Executive Dr, New Windsor · verified Sep 13
    See details

    A ribbon cutting ceremony will honor Mackey Catania & Whalen LLP. The occasion centers on the official cut of the ribbon to recognize the firm.

    Event website ↗
Friday, September 18 2 events
  • 5pm

    Town of Mount Hope Fall Festival

    Mount Hope Town Park, 42 Mt Hope Ave, Otisville · verified Sep 13
    See details

    The Town of Mount Hope Fall Festival brings a weekend filled with food, music, a parade, rides, fireworks, and more. A fireworks show is planned for Saturday. Vendor applications are open for those interested in participating.

    Event website ↗
  • 7pm

    CLUE

    233 Creamery Pond Rd, Chester · verified Sep 13
    See details

    A stormy night, a curious dinner invitation, and a mansion full of suspects set the stage for a comic mystery at Sugar Loaf Performing Arts Center Pavilion. At Boddy Manor, the host has turned up dead, aliases hide secrets, and a meticulous butler unveils an assortment of potential weapons. Iconic suspects Scarlet, Plum, White, Green, Peacock, and Mustard race to expose the culprit before the situation worsens. Inspired by the cult-favorite film and the classic board game, this brisk whodunit blends rapid-fire humor with surprises all the way to the final reveal. Presented by The Sugar Loaf Arts Collective and Greenwood Lake Theater, the experience unfolds in the Pavilion Theatre and brings the audience close to the action. Ticket options include VIP at $55 with a complimentary drink and premier seating, and General Admission at $45.

    Event website ↗
Saturday, September 19 10 events
  • 8:30am

    Trustee Time

    Java Blue Coffee & Market, 8 Union St, Montgomery · verified Sep 13
    See details

    Gather at Java Blue Coffee & Market for an informal conversation with a trustee. This casual coffee meetup invites anyone to bring questions, share feedback, and talk through any concerns in a welcoming setting. All are invited to take part in the discussion over a cup of coffee.

    Event website ↗
  • 10am

    Sew EZ Creations at the Pine Bush Harvest Festival

    Pine Bush Harvest Festival, 66 Main St, Pine Bush · verified Sep 13
    See details

    Sew EZ Creations will be on site as a vendor at the Pine Bush Lions Harvest Festival. Please note that Sew EZ Creations is not organizing this event and cannot assist with vendor spots. If you are interested in becoming a vendor, reach out to the Pine Bush Lions directly. Be cautious of Facebook scammers claiming to be organizers, and avoid responding to suspicious comments or direct messages.

    Event website ↗
  • 10am

    HVDHA Annual Fall Harvest and Festival

    Hoeffner Farms, 405 Goodwill Rd, Montgomery · verified Sep 13
    See details

    Enjoy an old-fashioned day centered on harvest traditions, with activities that include harvesting, corn, and work involving draft animals. Vendor space is available; for details, contact Wendy Calyer.

    Event website ↗
  • 11am

    Otisville Fire Company 100th Anniversary

    60 State St, Otisville · verified Sep 13
    Free

    The 100th anniversary celebration features a parade through the Village of Otisville that continues to the Town of Mount Hope Fall Festival. Fire departments, community groups, and EMS are invited to march. At the festival, look for a booth offering food, a challenge coin, and a supporter T-shirt. For marching inquiries, email Otisvillefirecompanysecretary@gmail.com.

    Event website ↗
  • 12pm

    Star Wars Unlimited - Ashes of the Empire Store Showdown

    3 Wallkill Ave, Montgomery · verified Sep 13
    See details

    Star Wars Unlimited Ashes of the Empire Store Showdown features a Premier Constructed format with a $20 entry fee. Matches are best of three with a 55 minute time limit. The event uses Swiss rounds with a top cut determined by the number of players: up to eight players play three Swiss rounds with no top cut, nine to sixteen players play four Swiss rounds and cut to Top 4, and seventeen to thirty two players play five Swiss rounds and cut to Top 8. Prize support comes from the Store Showdown Kit, with a Hera Syndulla promo for every entry and Grogu Foil Top promos for top placements from Top 8 through the winner. Additional booster packs and Carbonite prizes are based on the total number of players.

    Event website ↗
  • 1pm

    Jersey Swamp Cats at Wright Family Farm

    Wright Family Farm, 335 Kings Hwy, Warwick · verified Sep 13
    See details

    Ride a hayride to the concert stage at Wright Family Farm for the Jersey Swamp Cats’ debut at the venue. The band will deliver jump blues, New Orleans rhythm and blues, and vintage rock and roll, highlighted by their signature back-and-forth between guitar and piano.

    Event website ↗
  • 1pm

    Outdoor Activities and Welcome BBQ

    Camp Bullowa, Stony Point · verified Sep 13
    See details

    This gathering at Camp Bullowa features outdoor activities and a welcome barbecue. Cub Scouts is open to all boys and girls in kindergarten through 5th grade.

    Event website ↗
  • 6:30pm

    The Beatles Candlelight Experience In Newburgh, NY - Saturday September 19th

    Christ Lutheran Church Newburgh, NY, 186 Fullerton Ave, Newburgh · verified Sep 13
    See details

    Presented by Lumos, this classical tribute to The Beatles takes place at Christ Lutheran Church in Newburgh. A string trio performs songs including Come Together, Here Comes the Sun, Eleanor Rigby, Yesterday, Twist and Shout, Good Day Sunshine, Lady Madonna, Blackbird, Get Back, Let It Be, Penny Lane, All You Need Is Love, Something, Yellow Submarine, Help, and Hey Jude. Two sittings are offered. Seating is first come, first served within your chosen tiered zone, available in Platinum, Gold, Silver, or Bronze. The venue is wheelchair accessible, though front row placement cannot be guaranteed. This event is for ages eight and older. Lumos partners with churches and venues across the United States and makes a donation to a different charity each month.

    Event website ↗
  • 8pm

    Moonflower Classic Rock @ The Union House Inn

    22 Hepper St, Walden · verified Sep 13
    See details

    Moonflower takes the stage at The Union House Inn for a debut performance filled with classic rock favorites and timeless anthems. Enjoy live music alongside great food and ice cold drinks, with plenty of chances for dancing and sing along moments. There is no cover charge.

    Event website ↗
  • 8pm

    Next Stop Comedy at Drowned Lands Brewery

    251 State School Rd, Warwick · verified Sep 13
    See details

    Next Stop Comedy brings stand-up to Drowned Lands Brewery with a fresh roster each time. Every show spotlights comedians who have appeared on TV and on podcasts, creating a rotating showcase of different acts at each performance.

    Event website ↗
Sunday, September 20 0 events
Monday, September 21 0 events
Tuesday, September 22 1 event
  • 4pm

    Ribbon Cutting: Montgomery Veterinary Hospital

    718 River Rd, Montgomery · verified Sep 13
    See details

    A ceremonial ribbon cutting will take place for Montgomery Veterinary Hospital. The event formally marks the occasion for the practice.

    Event website ↗
Wednesday, September 23 4 events
  • 2pm

    Lunch & A Show

    Sugar Loaf Performing Arts Center Pavilion, 233 Creamery Pond Rd, Chester · verified Sep 13
    See details

    Experience a relaxed meal paired with a live performance at Sugar Loaf Performing Arts Center Pavilion. The Acchords, featuring Tommy, Warren, Joe, and Dennis, bring tight harmonies and high energy as they move from timeless favorites to contemporary tunes across a variety of genres. The price is $65 per person and includes lunch and the show. Food is by Graze & Ice Capps, with menu details to be announced.

    Event website ↗
  • 6pm

    Becoming a Master Gardener Volunteer Discussion Panel

    Cornell Cooperative Extension Orange County, 18 Seward Ave, Middletown · verified Sep 13
    See details

    Learn what it takes to become a Master Gardener Volunteer with Cornell Cooperative Extension Orange County at a discussion panel featuring experienced volunteers and the program coordinator. The session covers how to apply, how the training works, and what the volunteer role is like. Attendance at one of the two panels is required for those who plan to apply for the next Master Gardener Volunteer training. Applications will be shared with registrants and must be submitted by the stated deadline. This event is free.

    Event website ↗
  • 6:30pm

    Blues Jam Session

    Meadow Blues Coffee, 8 Greycourt Ave, Chester · verified Sep 13
    See details

    A blues jam session hosted by Dylan Doyle, a musician with roots in the South and an upbringing in the North. He began shaping his musical voice early in life and now blends R&B, Americana, and funk within the blues. His influences span Jimi Hendrix, Wes Montgomery, John Mayer, D’Angelo, Bob Dylan, John Prine, The Band, Chris Stapleton, Bill Withers, and Roberta Flack. The music centers on a sound that is distinctly American, guided by that broad lineage.

    Event website ↗
  • 6:30pm

    Pride Book Club: According to Plan by Christen Randall

    The White Knight's Game Room, Inc. "In Haven", 110 Main Street, Lock Haven · verified Sep 13
    See details

    This month's selection is According to Plan by Christen Randall.

    Event website ↗

All upcoming events78 more events through Dec 11

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

Friday, September 25 6 events
  • 9am

    Emmy's Treasure Chest

    Goshen Farmers Market, 255 Main St, Goshen · verified Sep 13
    Free

    Emmy’s Treasure Chest brings stylish, budget-friendly $8 treasures to the Goshen Farmers Market. Attendees can browse accessories and other standout finds, with options to suit a range of tastes. Support a small business while discovering affordable pieces.

    Event website ↗
  • 2pm

    Caitlin Moran: How To Be Hopeful - 25 Sept 2026

    Arts Centre, 43 West St, Warwick · verified Sep 16
    See details

    Caitlin Moran brings How To Be Hopeful to the stage in a live appearance at the Arts Centre in Warwick.

    Event website ↗
  • 4pm

    Barry's Grove Pre-Harvest Gathering

    James Olley Park, Walden · verified Sep 16
    Free

    This free community event at James Olley Park features activities for children, food, and live entertainment. Guests can fish at the pond and enjoy the disc golf course at their own pace. Further details will be announced.

    Event website ↗
  • 8pm

    Men of Soul

    Paramount Theatre of Middletown, 17 South St, Middletown · verified Sep 13
    See details

    The Men of Soul deliver a high energy tribute to classic and contemporary Soul and R&B. This East Coast trio of powerhouse vocalists performs with a tight six piece band featuring accomplished Tri State Area musicians, creating rich harmonies and dynamic grooves from start to finish. The set spans eras and styles, from the silky sound of Philly Soul to the feel good funk of the 70s and 80s, the chart shaping hits of the 90s and 2000s, and even yacht rock favorites, with nods to artists like Earth, Wind & Fire. Known across the region as a premier tribute experience, the show blends precision, passion, and showmanship for a night of timeless songs and nonstop energy.

    Event website ↗
  • 9pm

    Iron Cobra Returns

    The Union House Inn, 22–24 Hepper Street, Walden · verified Sep 13
    See details

    www.IronCobraRocks.com

    Event website ↗
  • 9pm

    Iron Cobra

    The Union House Inn, 22 Hepper St, Walden · verified Sep 13
    See details

    Iron Cobra returns to Union House Inn with a high energy arena rock show featuring music from AC/DC, Led Zeppelin, Van Halen, Mötley Crüe, Def Leppard, and more. Marking two decades on the scene and still bringing the heat, the band delivers an all-out night of classic rock.

    Event website ↗
Saturday, September 26 4 events
  • 9am

    University of Scouting

    Camp Bullowa Summer Day Camp, 15 Franck Rd, Stony Point · verified Sep 13
    See details

    University of Scouting returns in a refreshed format for today’s scouting leaders and youth. Instead of classroom-based activities, the program centers on practical, hands-on learning. Modules are tailored for Cub Scout leaders, troop leaders, older youth, and commissioners. The event takes place at Camp Bullowa Summer Day Camp. Class schedules are expected to be available.

    Event website ↗
  • 11am

    Sew EZ Creations

    Walden Municipal Square, Walden · verified Sep 13
    See details

    Sew EZ Creations will be at the Walden Harvest Fest at Municipal Square as a participating vendor. Inquiries about vendor opportunities should be directed to the Walden Community Council, the festival’s organizer, as Sew EZ Creations is not able to assist with vendor spaces. Please watch for fraudulent Facebook accounts that claim to organize the event, and avoid responding to suspicious comments or direct messages.

    Event website ↗
  • 6pm

    The Field of Residence

    Maple Meadow, 131 Old Ridge Rd, Warwick · verified Sep 13
    See details

    A full moon equinox community sound immersion unfolds in an open meadow in Warwick, where ten sound healers form a circle around participants. There is no stage. Live tones from crystal bowls, gongs, chimes, and other sacred acoustic instruments rise from every direction as daylight fades and the moon appears. The focus is on many voices and many instruments working together to create one shared field of sound for deep rest. Capacity is intentionally limited, and admission is $55.

    Event website ↗
  • 8pm

    Hotel California: The Original Eagles Tribute

    Sugar Loaf Performing Arts Center, 233 Creamery Pond Rd, Chester · verified Sep 13
    See details

    At Sugar Loaf Performing Arts Center, Hotel California delivers a faithful celebration of the Eagles, honoring the band’s music with decades of touring experience around the globe. Widely regarded as a premier stand in for the original group, they have filled outdoor spaces and arenas, shared bills with the Doobie Brothers, Lynyrd Skynyrd, Styx, Gretchen Wilson, and REO Speedwagon, and performed in India, Bermuda, Dubai, Japan, Tahiti, and across North America. The show highlights close lead vocal likeness, precise instrumentation, soaring harmonies, and high-caliber stagecraft, all shaped by more than a century of combined professional experience. Ticket options include VIP Rows A-D at $79 with VIP entrance, early admission, one free drink, and an SLPAC T-shirt. Main floor seating is available in Rows E-M for $55 and Rows N-Z for $45. Balcony seating is offered in Rows A and D for $55, and in Rows B, C, E, F, and G for $35.

    Event website ↗
Sunday, September 27 2 events
  • 11:30am

    Sunday Brunch

    All One One All Farm, 221 Craigville Rd, Goshen · verified Sep 13
    See details

    Experience a family-friendly seasonal brunch at the farm, built around fresh, locally sourced ingredients that are grown and prepared with care. Each gathering presents a set menu that showcases the best of the season, served in a warm and welcoming farm setting. The meal is prix fixe, and reservations are required. Menu details will be shared soon.

    Event website ↗
  • 6pm

    Jeff Dye

    Sugar Loaf Performing Arts Center Pavilion, 233 Creamery Pond Rd, Chester · verified Sep 13
    See details

    Jeff Dye delivers bold, high-volume stand-up at Sugar Loaf Performing Arts Center Pavillion, breaking past polite conversation to spark big laughs. He is a regular on Gutfeld and The Joe Rogan Experience, and audiences may know him from MTV’s Money From Strangers, NBC’s Better Late Than Never, and appearances on The Tonight Show. Expect sharp, loud, and irreverent comedy centered on blunt honesty, performed with fearless energy.

    Event website ↗
Tuesday, September 29 1 event
  • 3pm

    Becoming Bodhisattvas – Learning To Let Go With The Heart Sutra | A silent meditation retreat

    14 Mary's Way, Garrison · verified Sep 13
    See details

    A silent, in-person meditation retreat led by Ethan Nichtern, Maho Kawachi, Lou Sharma, and Eric Gerard centers on the Bodhisattva path through study and practice of the Heart Sutra, with a special emphasis on learning to let go without spiritual bypassing or avoidance. Teachings explore how to release beliefs that no longer serve and how to meet upheaval with compassion and clarity, guided by Avalokitshvara’s instruction on freedom, possibility, and pre-conceptual insight. Three and a half days are held in functional silence outside of lectures and Q and A to support deep practice, and the final full day is devoted to interpersonal processing and community integration. No previous familiarity with these teachings is expected. The schedule also includes an optional ceremony to take or reaffirm the Refuge or Bodhisattva Vow within the Tantric, Vajrayana framework. Taking the Bodhisattva Vow requires that the Refuge vows have already been taken in any lineage, and participants may attend the ceremony whether or not they choose to formally take a vow. The retreat is open to Buddhist practitioners, Buddh-ish participants, and those who prefer not to use labels.

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

    2026 Arts and Culture Festival

    Fei Tian College Northern Campus, 65 Seward Ave, Middletown · verified Sep 13
    See details

    The second Arts and Culture Festival brings together creativity, culture, community, and innovation. Expect visual art and creative displays, live performances and cultural programs, hands-on workshops paired with family activities, local cuisine and distinctive vendors, as well as opportunities to connect with artists and community organizations. Whether you are drawn to art, culture, or food, or simply want a meaningful outing with family and friends, this festival offers something for a wide range of interests and continues to grow as a community tradition.

    Event website ↗
Friday, October 2 2 events
  • 8pm

    Marshall Charloff & Purple Xperience

    Sugar Loaf Performing Arts Center, 233 Creamery Pond Rd, Chester · verified Sep 13
    See details

    At Sugar Loaf Performing Arts Center, Marshall Charloff & The Purple xPeRIeNCE present a faithful, high-energy celebration of Prince’s music, created in Minneapolis by Marshall Charloff and Matt “Doctor” Fink of Prince & The Revolution in 2011. The production was conceived to deliver the songs entirely live without backing tracks, while honoring the iconic visuals through thoughtful costuming and likeness. Now in its 15th year of touring across the country and abroad, the show has entertained more than a million fans. Highlights include official licensing by the Prince Estate in 2019 and a featured appearance in the USA Pavilion at the World Expo in Dubai in 2021. Audiences can expect a performance that is fully live from start to finish with a focus on musicianship. Marshall Charloff, seen with leading symphonies and as a headliner at Red Rocks Amphitheater, also mounted a solo residency in Las Vegas, and he fronts a band of Minneapolis all-star players for this experience. Ticket options include VIP seats in rows A through D at $89 with VIP entrance, early entry, one free drink, and an SLPAC T-shirt. Seats in rows E through M are $78. Seats in rows N through Z are $69. Balcony rows A and D are $69, and balcony rows B, C, E, F, and G are $55.

    Event website ↗
  • 8pm

    Live and Let Die

    Paramount Theatre of Middletown, 17 South St, Middletown · verified Sep 13
    See details

    An expansive symphonic concert celebrates Paul McCartney’s music, led by Tony Kishman, a veteran of Broadway’s Beatlemania whose portrayal has earned praise from Beatles producer George Martin and from McCartney himself. A 12 piece orchestra brings added depth and power as favorites like Live and Let Die, Hey Jude, Penny Lane, and Maybe I’m Amazed take center stage, performed with precision and heart. With world class musicians, immersive visuals, and refined production, the show turns timeless hits into a live experience with a cinematic feel.

    Event website ↗
Saturday, October 3 5 events
  • 8am

    HVDS Show at WillsWay Equestrian Center

    WillsWay Equestrian Center, 270 Conklingtown Rd, Goshen · verified Sep 13
    See details

    This HVDS show takes place at WillsWay Equestrian Center. Entries are accepted during a set opening period and close by the listed deadline, so participants should plan ahead to submit within the designated window.

    Event website ↗
  • 10am

    2026 Gardening Classes

    Cornell Cooperative Extension Orange County Office, 18 Seward Ave, Middletown · verified Sep 13
    See details

    Master Gardener Volunteers present a series of stand-alone gardening classes, and you can register for as many sessions as you like. The program spans topics such as making maple syrup at home, cultivating shiitake mushrooms on logs, and starting seeds outside through winter sowing. Other classes explore soil fundamentals and sustainable practices, planning and caring for a productive vegetable garden, and adding fruit to the backyard, from apples and pears to pawpaws, serviceberries, raspberries, and strawberries. Composting is covered with guidance on what and where to compost, practical bin ideas, and vermicomposting. Additional sessions focus on using cover crops to protect and enrich garden soil, integrating native plants into existing beds with time to review photos, site plans, and plant lists and create a multi‑year plan, and identifying beneficial and harmful insects with an opportunity to apply new skills outdoors. Design-minded gardeners can learn core principles of landscape design and get step-by-step direction for reducing or replacing lawn, including goal setting, budgeting, site assessment, preparation, plant selection, and establishing a wildflower meadow. Seasonal care is addressed with a class on preparing the garden for winter, including what to cut back, what to leave for wildlife and protection, and ways to guard plants from wind and deer. A session on native grasses highlights durable, low‑maintenance choices and how to match species to moist or dry conditions. In the event of severe weather, select classes move online. The fee is $10 per class, with a solidarity option available at no cost for those who cannot pay at this time.

    Event website ↗
  • 11am

    Fenders N’ Flannels

    Hoeffner Farms, 405 Goodwill Rd, Montgomery · verified Sep 13
    See details

    Fenders N’ Flannels is an annual truck show that supports breast cancer awareness. The previous event raised more than $10,000, and organizers are working to make the upcoming edition even bigger. It offers a chance for truck enthusiasts to showcase their vehicles while contributing to a meaningful cause.

    Event website ↗
  • 12pm

    Hudsonfest 2026

    The Ellis Newburgh, 60 Dubois Street, Newburgh · verified Sep 13
    Free

    HUDSONFEST 2026 returns to The Ellis with free admission for all ages. A new artist lineup and vendors will be announced.

    Event website ↗
  • 1pm

    McMule

    Wright Family Farm, 335 Kings Hwy, Warwick · verified Sep 13
    See details

    Moonshine brings its picking to Wright Family Farm. The farm offers activities for all ages, with plenty to explore throughout the grounds. The atmosphere centers on a crisp fall day in the country.

    Event website ↗
Sunday, October 4 3 events
  • 9am

    36th Annual Warwick Applefest

    Village of Warwick, Warwick · verified Sep 13
    See details

    Orange County, NY's biggest festival returns for its 36th year, featuring unique craft vendors and food vendors, a carnival for kids, animals, and more. This family event offers a range of activities intended to appeal to all ages.

    Event website ↗
  • 6pm

    Kristin Key Live

    Sugar Loaf Performing Arts Center, 231 Creamery Pond Road, Chester · verified Sep 13
    See details

    Kristin Key performs live at Sugar Loaf Performing Arts Center in Chester, New York. See her on stage for an in-person show at the venue.

    Event website ↗
  • 6pm

    Kristen Key

    Sugar Loaf Performing Arts Center, 233 Creamery Pond Rd, Chester · verified Sep 13
    See details

    Kristin Key presents a lively blend of stand-up and musical comedy from a national headliner whose shows often sell out across the country. Her online videos have amassed more than 95 million views and a following of over 900,000 across social platforms. Dedicated to community uplift, she fosters welcoming spaces for audiences of all backgrounds and contributes to local nonprofits with each tour date. Recent recognition includes the North County LGBTQ Resource Center’s Award of Merit in 2024 and a place on the 2025 Curve Power List. Her work spans six full-length comedy albums and a DryBar special, with screen and airwave appearances on NBC’s Bring the Funny and Last Comic Standing, VH1, and SiriusXM. She also hosts Kristin Knows Blank, a comedy podcast featuring interviews and games with pop culture figures and rising comics, available on major streaming platforms. She is currently headlining an international tour.

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

    Monthly Community Yoga Class

    6 Broadway Ave, Chelsea · verified Sep 13
    See details

    This monthly, pay-what-you-can community yoga class welcomes people of all backgrounds and experience levels to practice Iyengar yoga together. The teaching focuses on alignment while building strength, increasing flexibility, and cultivating mindful awareness, with step-by-step guidance provided throughout. Suggested donation guidelines are available to help with choosing an amount, and participants may contribute what feels appropriate so the class remains accessible to the whole community.

    Event website ↗
Saturday, October 10 9 events
  • 10am

    Landscape Architecture in the Hudson Valley

    Goshen Public Library & Historical Society, 366 Main St, Goshen · verified Sep 13
    See details

    Woodbury Town Historian Alex Prizgintas explores the impact of renowned architects on the Hudson Valley, highlighting how their work shaped the region’s landscape architecture. This talk offers historical context on influential figures and the designs that left a lasting mark across the valley.

    Event website ↗
  • 11am

    Rick Hearst, Kristen Vaganos and Josh Kelly LIVE in Newburgh, NY

    Silk Factory, 299 Washington St, Newburgh · verified Sep 13
    See details

    Silk Factory in Newburgh welcomes a General Hospital fan gathering featuring Rick Hearst, Kristen Vaganos, and Josh Kelly. With Port Charles buzzing as the daughter falls for the cowboy, the trio offers candid conversation about on-screen chemistry, dramatic twists, and moments from behind the camera. Expect stories from the set, audience Q&A, and a lively stage presence that highlights The Dad, The Daughter & The Cowboy dynamic. Hearst, Vaganos, and Kelly appear as their well known characters Ric Lansing, Molly Lansing Davis, and Cody Bell, sharing how they bring these roles to life. VIP tickets at 150 dollars plus taxes and fees include premium seating along with a post show meet and greet with photo opportunities, autographs, and selfies. General Admission at 75 dollars plus taxes and fees is show only, and General Admission Standing at 55 dollars plus taxes and fees is show only.

    Event website ↗
  • 11am

    Colonial Era Food Preservation 11-4

    Fort Montgomery State Historic Site, 690 Route 9W, Fort Montgomery · verified Sep 13
    See details

    A live demonstration at Fort Montgomery State Historic Site highlights how people in the colonial era preserved food. The presentation focuses on period methods used to extend the life of provisions and offers a clear look at everyday practices from that time.

    Event website ↗
  • 1pm

    HV Empanada Festival 6

    People's Waterfront Park, 1 Washington St, Newburgh · verified Sep 13
    See details

    New York’s original empanada festival makes its return to the Newburgh Waterfront, celebrating more than 50 different ways to enjoy empanadas. The experience features food trucks, caterers, a variety of vendors, and live music. Vendors and sponsors are welcome, and tickets are available. It is all about eating, drinking, and empanadas.

    Event website ↗
  • 1pm

    Tulane Green Wave at Army Black Knights Football

    Michie Stadium, 700 Mills Rd, West Point · verified Sep 13
    See details

    Tulane Green Wave meets the Army Black Knights at Michie Stadium in West Point. The matchup features differing styles and tempo. Set in one of college football’s most distinctive venues, the pageantry, Hudson Valley scenery, and near-the-field sightlines make the action feel close from the opening kickoff.

    Event website ↗
  • 5pm

    Game Show Experience by Bob Scott

    Cronomer Valley Fire Department, 296 N Plank Rd, Newburgh · verified Sep 13
    See details

    Enjoy a buffet dinner in support of a fundraiser, followed by a lively competition show. Seating is limited, and group tickets are available. Tickets are processed through Givebutter to help keep costs down, and gratuities are optional.

    Event website ↗
  • 6pm

    First Responder Trauma Support Group

    Mental Health Association in Orange County, Inc., 73 James P Kelly Way, Middletown · verified Sep 13
    Free

    This group provides a confidential, welcoming space for first responders affected by traumatic stress to connect with others who understand and explore healthy ways to heal and move forward. It is open to fire, EMS, law enforcement, dispatchers, corrections, emergency communications, and ER or healthcare first responders. Participation is for peers only, no documentation is required, and there is no cost.

    Event website ↗
  • 7pm

    Cameron Brown and Dannie's Calypso

    The Chapel Restoration, 45 Market St, Cold Spring · verified Sep 13
    See details

    Cameron Brown and Dannie’s Calypso draws on the bassist’s early immersion in Miles Davis, formative work with Don Cherry, a decade alongside Don Pullen, George Adams, and Dannie Richmond, and extensive touring with Sheila Jordan, Dewey Redman, and Joe Lovano. The program blends original pieces with Don Cherry’s cocktail suite idea, threading multiple tunes into a single, continuous flow through a harmolodic approach. Within these suites, a wide range of material can appear, from early bebop selections to themes by Ornette Coleman and Don Cherry, melodies associated with Albert Ayler, and songs by Jobim. The ensemble features Cameron Brown on bass with Dave Ballou on trumpet, flugelhorn, and cornet, Jason Rigby on tenor and soprano saxophones, Lisa Parrott on baritone, alto, and soprano saxophones, and Tony Jefferson on drums and cymbals.

    Event website ↗
  • 8pm

    Foreign Journey

    Silk Factory, 299 Washington St, Newburgh · verified Sep 13
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    Silk Factory and PMG Presents host Foreign Journey, a tribute showcase honoring the music of Foreigner and Journey. The performance spans every era, highlighting chart-toppers and beloved deep cuts with high energy and faithful detail to the sound of these two iconic bands. The group has been building momentum across Long Island and the Tri-State region and is known for an electrifying set from start to finish. This is an all-ages event, and minors must attend with an adult. Full dinner service is available in the first floor restaurant, and reservations are required for the dining room. A $20 food and beverage minimum applies per ticket. All ticket sales are final with no returns or exchanges. Seating is first come, first served, and management may adjust seating layouts or assignments as needed based on attendance.

    Event website ↗
Sunday, October 11 4 events
  • 10am

    NerdOnGuitar

    Warwick Valley Farmers' Market, 38 Main St, Warwick · verified Sep 13
    Free

    Warwick Valley Farmers' Market features NerdOnGuitar alongside market vendors, pairing music with a relaxed market experience.

    Event website ↗
  • 2pm

    Fall Arts Fair

    Church of the Holy Innocents, 401 Main St, Highland Falls · verified Sep 13
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    This event features a market of artisan-made goods, a silent-bid auction, raffle drawings, and additional activities. Browse handmade items, place bids in the auction, and take part in raffles for an engaging arts-focused experience.

    Event website ↗
  • 3pm

    Jimmy Lee

    Edenville General Store, 240 Pine Island Tpke, Warwick · verified Sep 13
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    Jimmy Lee returns to Edenville General Store with a performance that blends country, bluegrass, and his own original songs. He shares his gratitude for the opportunity to come back, and the setting offers food to enjoy alongside the music.

    Event website ↗
  • 6pm

    Jason Salmon

    Sugar Loaf Performing Arts Center Pavilion, 233 Creamery Pond Rd, Chester · verified Sep 13
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    Enjoy a standup comedy show with Texas-born, New York City based comedian Jason Salmon at the Sugar Loaf Performing Arts Center Pavilion. His act mixes playful self-deprecation with sharp, unexpected insights. He has performed around the world, including shows for troops in Europe, South America, and Afghanistan. His special, BISCUITS and GRAVITY, is available on YouTube, and his credits include Red Dead Redemption 2, Orange Is the New Black, HBO, Comedy Central, At Home with Amy Sedaris, Hulu’s Wu-Tang Clan series, and 30 Rock. Tickets are offered at two levels, with VIP priced at $39 and general admission at $29.

    Event website ↗
Tuesday, October 13 1 event
  • 7pm

    Ghost Hunters' Steve Gonsalves Live: A Life with Ghosts -

    City Winery Hudson Valley, 23 Factory St, Montgomery · verified Sep 13
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    Steve Gonsalves, familiar from Ghost Hunters, Ghost Nation, The House Inbetween, and the bestselling book A Life with Ghosts, leads an immersive night of hauntings, history, and real accounts drawn from his extensive archive. This edition brings fresh stories, added historical insights, and footage not previously shared. Through personal testimony, rare video, haunted items, and candid behind-the-scenes insights, he opens up some of his most notable cases, the evidence collected, and the experiences gathered over years of investigation. He also digs into the authentic history tied to these moments, which can be just as disquieting as the reported activity. The program mixes humor with interaction with the crowd and a live Q&A, giving fans time to ask about techniques, findings, and the narratives behind the investigations. A limited number of VIP packages are offered. It is an intimate and thought-provoking evening with one of the most recognized voices in the paranormal.

    Event website ↗
Wednesday, October 14 1 event
  • 7pm

    Dr. Temple Grandin

    Paramount Theatre of Middletown, 17 South St, Middletown · verified Sep 13
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    At the Paramount Theatre of Middletown, this event features Dr. Temple Grandin, Ph.D., widely known as one of the most accomplished autistic adults and a noted expert in humane livestock handling. Her life story inspired the HBO film Temple Grandin, with Claire Danes portraying her on screen. Grandin was inducted into the American Academy of Arts and Sciences in 2016 and has shared her work through outlets such as NPR, ABC's Primetime Live, The Today Show, and the BBC special The Woman Who Thinks Like a Cow. She is among the few specialists worldwide who design livestock handling equipment and is known for speaking about autism and cattle handling. Her bestselling book Visual Thinking explores the strengths of people who think in pictures, patterns, and abstractions, and she has also delivered the TED talk The World Needs ALL Kinds of Minds.

    Event website ↗
Friday, October 16 2 events
  • 7pm

    The Addams Family Musical

    Sugar Loaf Performing Arts Center, 233 Creamery Pond Rd, Chester · verified Sep 13
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    The Sugar Loaf Arts Collective teams up with Core Theatre Group and Warwick Center for the Performing Arts to bring a musical comedy inspired by Charles Addams’ iconic family to the stage. The story explores love, family connections, and the ups and downs of growing up in true Addams style, brought to life by Broadway guest artists, music and lyrics by Andrew Lippa, and a book by Marshall Brickman and Rick Elice. Tickets are $79 for rows A through D, $55 for rows E through M, $45 for rows N through Z, $55 for balcony rows A through E, and $35 for balcony rows E through G.

    Event website ↗
  • 9pm

    Iron Cobra Returns

    Horse & Sulky Bloomingburg, 809 Bloomingburg Rd, Bloomingburg · verified Sep 13
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    Get set for an electrifying rock experience where the volume rises and the energy never lets up.

    Event website ↗
Saturday, October 17 4 events
  • 2pm

    Black Cat Bone Acoustic

    Applewood Winery, 82 Four Corners Rd, Warwick · verified Sep 13
    See details

    J.P. and Pete are making an appearance at Applewood.

    Event website ↗
  • 7:30pm

    Funny Women of a Certain Age

    Paramount Theatre of Middletown, 17 South St, Middletown · verified Sep 13
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    This stand-up showcase features Carole Montgomery alongside Monique Marvez and Tammy Pescatelli. Launched by Montgomery after decades on stage as a way to perform with her peers, it has grown into a recognized comedy series dedicated to giving seasoned women a strong spotlight. With a changing lineup of veteran comedians, the show has filled venues and led to three Showtime specials that set ratings records. The performers are trailblazers whose work helped open doors for many of today’s women in comedy.

    Event website ↗
  • 8pm

    Next Stop Comedy

    The Drowned Lands Brewery, 251 State School Rd, Warwick · verified Sep 13
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    Next Stop Comedy brings a rotating roster of stand-up talent to Drowned Lands Brewery, delivering a fresh lineup at every show. Expect comedians with television appearances and podcast credits, all gathered for an evening of sharp sets and big laughs.

    Event website ↗
  • 8:30pm

    Dean Shot and his Solid Senders

    Barrel 28 Restaurant, 29 N Main St, Florida · verified Sep 13
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    Dean Shot and his Solid Senders make their first appearance at Barrel 28 Restaurant in Florida, NY. The lineup features Earl Sauls on upright bass and Colby Inzer on drums. The setting is just over the New Jersey and New York border.

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

    Walk to End Alzheimer's - Rockland County

    Rockland Boulders Stadium, Pomona · verified Sep 13
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    At Rockland Boulders Stadium, the Alzheimer’s Association Walk to End Alzheimer’s brings Rockland County together to advance the fight against Alzheimer’s and all other dementia. With promising treatments emerging, the emphasis is on hope and keeping momentum strong within the community. Widely regarded as the largest fundraising event in the world dedicated to ending the disease, this walk offers a meaningful way to take action close to home.

    Event website ↗
Friday, October 23 1 event
  • 7pm

    Uncle Shoehorn's Big Easy at the Silk Factory - Newburgh NY - Fri. Oct 23, 7PM

    Silk Factory, 299 Washington St, Newburgh · verified Sep 13
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    Uncle Shoehorn's Big Easy & New Yorleans Horns brings a New Orleans style celebration to Silk Factory in Newburgh, NY. The nine piece group pays tribute to the sounds of the Crescent City with favorites by Doctor John, The Meters, the Neville Brothers, Preservation Hall Jazz Band, Galactic, Little Feat, Trombone Shorty, and more. Look forward to spirited grooves, bold brass, and a festive vibe... beads and dancing shoes encouraged.

    Event website ↗
Saturday, October 24 2 events
  • 9am

    Walk to End Alzheimer's - Orange/Sullivan County

    Benedict Farm Park, 1673–1703 NY-17K Montgomery‎ New York‎ 12549 United States, Montgomery · verified Sep 13
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    Hope is growing as new treatments emerge for Alzheimer’s and other dementias. This community walk, part of the Alzheimer’s Association Walk to End Alzheimer’s, helps keep that momentum going by raising funds to fight the disease. Recognized as the largest global fundraiser focused on ending Alzheimer’s, it unites participants in support of the cause.

    Event website ↗
  • 10am

    2026 Create an Autumn Wreath

    18 Seward Ave, Middletown · verified Sep 13
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    Explore the colors and textures of fall at a hands-on workshop where participants create a custom wreath using natural dried flowers, leaves, and other seasonal accents. The fee is $35 per person and covers all materials to make one wreath. Enrollment is limited to 20 participants. There are no refunds, and if you cannot attend you may send someone in your place.

    Event website ↗
Sunday, October 25 4 events
  • 8am

    Kiwanis Scholarship Run/Walk

    Chadwick Lake, 1702 Route 300, Newburgh · verified Sep 13
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    The Kiwanis Club of Newburgh Scholarship Run/Walk brings a family-friendly 4-mile trail experience to Chadwick Lake Park in Newburgh, New York. Participants follow a scenic loop around the lake while helping fund scholarships and educational and enrichment opportunities for children and students through the Kiwanis Club of Newburgh Foundation. The event features music from K104 with special guest Skywalker, breakfast and refreshments such as eggs and sausage, coffee, sports drinks, muffins, croissants, fruit and snacks, along with gift-basket raffles from local businesses and health and wellness vendors. Registered participants receive a Color Cube T-shirt. Age-group winners earn custom awards from FCC Gallery & Awards, and the overall male and female finishers each receive a $100 cash prize. Dogs are welcome, and registration covers Chadwick Lake Park entry. Open to competitive runners, casual walkers, families, local residents and visitors to the Hudson Valley, this 4-mile run and walk offers a chance to stay active outdoors while supporting young people in the community.

    Event website ↗
  • 8:30am

    We Can Be Heroes 5K Run/Walk & Kids Fun

    Orange County Airport - MGJ, 500 Dunn Rd, Montgomery · verified Sep 13
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    Honor everyday heroes at the 9th annual We Can Be Heroes 5K Run Walk and Kids Fun Run. Participants can run or walk on the runway at Orange County Airport, pairing a memorable course with a mission to raise awareness and funds for Fearless! Hudson Valley. Runners and walkers of all ages are welcome. Registration offers options for individuals, pairs, and groups of three or more, and the Kids 1/4 Mile Fun Run is free. All proceeds support Fearless! and its education, prevention, and advocacy work, as well as comprehensive services that include shelter for victims and survivors of interpersonal violence, human trafficking, sexual violence, and other forms of crime victimization.

    Event website ↗
  • 9:30am

    Halloween Hunter Pace

    Quiet Creek Stable LLC, 552 RT-94, Vernon · verified Sep 13
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    Quiet Creek Stable LLC hosts a Halloween Hunter Pace that welcomes riders from all disciplines. Costumes are optional and encouraged, and jumping is not required since every jump offers a go-around. The event features Open, Novice, and Hilltopping divisions, with ribbons awarded through sixth place. It is part of the Virginia Martin Memorial Pace Series, with overall awards determined by points that include results from this pace and the Thanksgiving Hunter Pace for those who ride at least three of the Fall Windy Hollow Hunt and Quiet Creek paces. Pre-registration is required by emailing a completed entry form in advance, and day-of entries are not accepted. Riders under 18 must provide a parent or trainer signature on the entry. Helmets and a current coggins are needed. Entry fees are $60 for adults and $35 for juniors. Tailgating is welcome until the fields close.

    Event website ↗
  • 11:30am

    Sunday Brunch at AOOA Farm

    221 Craigville Rd, Goshen · verified Sep 13
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    A family friendly brunch celebrating the season features fresh local ingredients that are grown and prepared with care. Each gathering offers a set menu that showcases peak seasonal flavors, served in a warm, welcoming farm setting. This is a prix fixe experience and reservations are required. Detailed menu information will be shared soon.

    Event website ↗
Wednesday, October 28 1 event
  • 6:30pm

    Blues Jam Session Hosted by Tony Vee

    8 Greycourt Ave, Chester · verified Sep 13
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    Tony Vee leads a live blues jam with the stage ready and the groove set. Known as the Gitfiddle Man, he ignites the energy and keeps the music flowing all night. Musicians and listeners can enjoy the scene, whether stepping up to play or settling in to take it all in. A $15 food and drink minimum applies.

    Event website ↗
Friday, October 30 1 event
  • 6pm

    YMCA's 6th Annual Gala

    City Winery Hudson Valley, 23 Factory St, Montgomery · verified Sep 13
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    A festive evening of celebration and connection supports the YMCA’s mission to strengthen the community through youth development, healthy living, and social responsibility. The evening includes flavorful food and beverages, live performances, and a silent auction featuring special items and one of a kind experiences. There are also opportunities to meet fellow community members, local leaders, and other YMCA supporters. Proceeds from each ticket help fund YMCA programs and services that provide long term benefits for children, families, and individuals across the community. Tickets are $200 for an individual and $350 for a couple.

    Event website ↗
Saturday, October 31 1 event
  • 8am

    Save the Date! Skyline's Fast CAT 10/31 & 11/1

    120 Tetz Ln, Middletown · verified Sep 13
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    Skyline brings back an AKC Fast CAT weekend following a strong turnout and positive feedback from its inaugural event. The focus is a fun mix of racing, titles, and community over two days. Expect familiar participants returning, along with dogs trying Fast CAT for the first time. Additional details, including the premium and entry information, will be shared as the event approaches.

    Event website ↗
Friday, November 6 1 event
  • 7pm

    Dylan Doyle Band

    8 Greycourt Ave, Chester · verified Sep 13
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    The Dylan Doyle Band presents a soulful blend that weaves R&B, Americana, and funk into one cohesive style. With roots in the South and an upbringing in the North, Dylan Doyle draws on wide ranging inspirations that include Jimi Hendrix, Wes Montgomery, John Mayer, D’Angelo, Bob Dylan, John Prine, The Band, Chris Stapleton, Bill Withers, and Roberta Flack. Known from a young age for imaginative interpretations, he shapes these influences into a sound that feels distinctly American.

    Event website ↗
Saturday, November 7 3 events
  • 10am

    2026 Natural Plant Dyes - Hands-on Workshops

    18 Seward Ave, Middletown · verified Sep 13
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    Explore the color potential of plants in a hands-on workshop led by local artisan Kirsten Gabrielsen. She grows and forages materials such as cosmos, goldenrod, phragmites, coreopsis, amaranth, chamomile, and indigo, then turns blooms and leaves into vivid dyes for natural fiber yarns. Learn how to create a spectrum of hues from plants that can be grown in Orange County while walking through each step of the dyeing process. The session begins with an overview of making plant-based dyes, then moves into a practical project. Participants will prepare dye from plants, dye yarn, and take home two sample skeins of naturally colored yarn. Hand-dyed yarn will be available for purchase after the workshop. Registration is limited to the first 12 people. The fee is $30 per person and includes all materials to dye two sample skeins. There are no refunds. If you cannot attend, you may send someone in your place.

    Event website ↗
  • 1pm

    Air Force Falcons at Army Black Knights Football

    Michie Stadium, 700 Mills Rd, West Point · verified Sep 13
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    Air Force visits Army at Michie Stadium in West Point, New York. This meeting between military academies highlights hard-nosed, well-drilled play and methodical, time-managing strategies, where every drive can feel decisive. With the venue beside the Hudson River, the setting underscores a deep sense of heritage and spectacle that offers a distinctive college football experience.

    Event website ↗
  • 7:30pm

    The Spinners

    Paramount Theatre of Middletown, 17 South St, Middletown · verified Sep 13
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    The Spinners take the spotlight for a performance grounded in more than six decades of R&B heritage. Recognized for smooth harmonies, memorable hooks, and a refined stage presence, the group built a catalog that anchors classic soul. Their national breakthrough came during their Motown era with the single Its a Shame, produced and co written by Stevie Wonder, which rose to number 14 on the Billboard Hot 100 and made a strong impact in R&B. Their greatest commercial streak followed in the 1970s when Henry Fambrough, Billy Henderson, Pervis Jackson, Bobbie Smith, and Philippé Wynne collaborated with producer Thom Bell, shaping the Philadelphia soul sound and turning out a remarkable run of hits.

    Event website ↗
Tuesday, November 10 1 event
  • 7pm

    Megan Woods - Montgomery, NY

    2135 State Route 208, Montgomery · verified Sep 13
    See details

    Megan Woods brings The Truth Tour to Goodwill Church in Montgomery, NY, joined by Jeremy Rosado, recognized from American Idol and The Voice. Expect an evening centered on worship, heartfelt connection, and a clear focus on God’s truth as Megan shares the music and stories that have connected with audiences nationwide. After a standout year and a successful spring leg, the tour returns for an expanded 30-city journey across the United States, continuing the momentum of her first headlining run. Tickets are on sale. VIP, early entry, and general admission options are planned, and the schedule may be adjusted. To protect buyers, TPR does not permit third party ticket resales on its event pages. Use the official ticketing outlet, since purchases from other sellers are not guaranteed and may limit access to updates or assistance.

    Event website ↗
Friday, November 13 1 event
  • 8pm

    Iron Cobra Debuts at Hurricane Grill and Wings!

    Hurricane Grill & Wings (829 Broadway, Newburgh, NY), 829 Broadway, Newburgh · verified Sep 13
    Free

    Iron Cobra brings its first-ever show to Hurricane Grill & Wings in Newburgh, and admission is free. Promoted as a debut to remember, this kickoff performance marks a new start for the act at the venue.

    Event website ↗
Sunday, November 15 1 event
  • 3pm

    Jimmy Lee at The Edenville General Store

    Edenville General Store, 240 Pine Island Tpke, Warwick · verified Sep 13
    See details

    Jimmy Lee returns to Edenville General Store for a live performance featuring country music, bluegrass, and his own original songs. Food from the general store is available to enjoy with the music.

    Event website ↗
Wednesday, November 18 1 event
  • 2pm

    Lunch & A Show - Country Jamboree

    233 Creamery Pond Rd, Chester · verified Sep 13
    See details

    Lunch & A Show is a new format at the Sugar Loaf Performing Arts Center that pairs a meal with live entertainment. This edition features The Country Jamboree, a salute to the golden era of country music. A seasoned cast, with backgrounds that include sharing stages with many of the genre’s most popular artists, performs songs associated with Johnny Cash, Patsy Cline, Willie Nelson, Merle Haggard, Loretta Lynn, Hank Williams and others. The program evokes the spirit of the Grand Ole Opry, moving from high-energy hoedown numbers to heartfelt love songs in a single, cohesive show. Lunch is served before the performance.

    Event website ↗
Saturday, November 21 3 events
  • 3:30am

    East Carolina Pirates at Army West Point Black Knights Football

    U S Military Academy - Michie Stadium, 700 Mills Road, West Point · verified Sep 13
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    The East Carolina Pirates head to Michie Stadium for a showdown with the Army West Point Black Knights. The game features differing on-field styles and unfolds in a notably distinctive college football venue. Tickets are available for those who want to experience it in person.

    Event website ↗
  • 10am

    2026 Create a Fall Pumpkin Centerpiece

    18 Seward Ave, Middletown · verified Sep 13
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    Create a festive fall centerpiece inside a ceramic pumpkin, perfect for bringing Thanksgiving spirit to your home. Instructors will guide you through choosing flower varieties, properly conditioning fresh blooms, and arranging them into a finished design. Each participant completes a fresh floral centerpiece, and all materials are included with registration. The fee is $30 per person. Space is limited to the first 20 people. Registrations are nonrefundable, and if you cannot attend you may send someone in your place.

    Event website ↗
  • 8pm

    Chester, NY: Matt Fraser – America’s Top Medium LIVE

    Sugar Loaf Performing Arts Center, 231 Creamery Pond Road, Chester · verified Sep 13
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    Seen on television delivering readings to audiences worldwide, Matt Fraser brings a 90 minute, interactive evening to Sugar Loaf Performing Arts Center. A New York Times bestselling author promoted as the nation’s top psychic medium, he shares messages from loved ones in spirit in real time, moving through the audience to offer readings that include names, memories, dates, and other personal details. As messages unfold in the moment, emotional and specific connections can lead to comfort, healing, laughter, and tears, and skeptics in the crowd often change their minds. Even when a reading is meant for someone else, many attendees feel the insights speak to them and leave feeling they heard exactly what they needed. Every seat offers the chance to be close to the experience, and no two nights are the same since the flow is guided by spirit and shaped by the people in the room. Presented as more than a show, it is framed as a shared experience that affirms love continues beyond this life. Tickets are limited and the event is expected to sell out.

    Event website ↗
Sunday, November 22 2 events
  • 9:30am

    Quiet Creek Thanksgiving Hunter Pace

    Quiet Creek Stable LLC, 552 RT-94, Vernon · verified Sep 13
    See details

    Quiet Creek Stable hosts a Thanksgiving Hunter Pace that welcomes riders of every discipline. This event is part of the Virginia Martin Memorial Pace Series, and results here help decide the overall winners based on the highest points earned by riders who have participated in at least three of the fall Windy Hollow Hunt and Quiet Creek hunter paces. Advance registration is required by emailing a completed entry form, with the process and form to be posted, and same-day entries are not accepted. Riders can choose among Open, Novice, and Hilltopping divisions, with ribbons awarded through sixth place in each. Jumps are optional and each has a go-around. Helmets and a current coggins are required, and riders under 18 must submit a parent or trainer signature on the entry. Entry fees are $60 for adults and $35 for juniors. Tailgating is welcome.

    Event website ↗
  • 10am

    Warwick Pottery Annual Show and Sale

    11 Hamilton Ave, Warwick · verified Sep 13
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    The annual show and sale from Warwick Pottery features handmade pottery presented in a lively, festive atmosphere. It offers a warm kickoff to the holiday season, with a curated selection of pieces available for purchase.

    Event website ↗
Wednesday, November 25 1 event
  • 9pm

    Iron Cobra Thanksgiving Eve Party at the ALL NEW Union House Inn!

    The Union House Inn, 22–24 Hepper Street, Walden · verified Sep 13
    See details

    www.IronCobraRocks.com

    Event website ↗
Sunday, November 29 1 event
  • 2pm

    Acoustic Nailedshutt at Clearview Vineyards

    Clearview Vineyard and Winery, 35 Clear View Ln, Warwick · verified Sep 13
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    Nailedshutt brings an acoustic set to Clearview Vineyard and Winery, blending alternative country, newgrass, country rock, blues, and reggae with acoustic interpretations of Grateful Dead songs. The focus is on a rootsy, unplugged sound that moves from twang and bluegrass touches to bluesy and reggae grooves.

    Event website ↗
Thursday, December 3 1 event
  • 9am

    Resorts World Catskills Holiday Casino Trip

    555 Union Ave, New Windsor · verified Sep 13
    See details

    Spend a day at Resorts World Catskills Casino in Monticello, New York, where slots and table games await. The trip costs $50 for residents and $65 for nonresidents and includes $25 in free slot play, a $15 food credit, and bus transportation. Departure is from the Marasco Senior Center, with a same-day return.

    Event website ↗
Friday, December 4 4 events
  • 10am

    2026 Create a Kissing Ball

    18 Seward Ave, Middletown · verified Sep 13
    See details

    Create a festive kissing ball with fresh evergreens at a hands-on holiday workshop. It begins with an introduction to a variety of greens and a step-by-step demonstration, then participants form small groups and work alongside Master Gardener Volunteers to craft a finished piece. Attendees are encouraged to bring gloves and clippers. Registration is limited, with two sessions offered that cap attendance at 20 in one and 9 in the other. The fee is $50 per person and includes all materials needed to make one kissing ball. There are no refunds, but if you cannot attend you may send someone in your place.

    Event website ↗
  • 2pm

    2026 Create a Holiday Wreath

    18 Seward Ave, Middletown · verified Sep 13
    See details

    Celebrate the season by crafting a fresh, fragrant wreath at a hands-on workshop that showcases an array of beautiful evergreens. The session begins with a guided overview of the different greens and a step-by-step demonstration, then participants team up in small groups with support from Master Gardener Volunteers to build a custom wreath. It is designed as a family-friendly activity. Please bring work gloves and a pair of clippers. Space is limited to 20 people per session. The fee is $50 per person and covers all supplies needed to make one wreath. Registrations are nonrefundable. If plans change, you may have someone attend in your place.

    Event website ↗
  • 2pm

    2026 Create a Tabletop Tree

    18 Seward Ave, Middletown · verified Sep 13
    See details

    Create a festive tabletop tree using fresh greens at a hands-on workshop. The session begins with a guided look at the different types of greenery followed by a demonstration. Participants then collaborate in small groups with support from Master Gardener Volunteers to craft a unique tree, making it a project families can enjoy together. Attendees are encouraged to bring gloves and clippers. Enrollment is limited to 20 people per session. The fee is $50 per person and includes all materials for one tabletop tree. Refunds are not available, and if a registrant cannot attend, another person may participate in their place.

    Event website ↗
  • 7pm

    Ryan Marks Band

    8 Greycourt Ave, Chester · verified Sep 13
    See details

    Ryan Marks Band delivers a trippy blend of funk, rock, blues, and improvisation, turning each performance into a fresh, cosmic journey where no two sets unfold the same way. Embracing surprise at every turn, they reinvent favorites from the 60s through the 90s with nods to artists such as Pink Floyd, Hendrix, Alice In Chains, Phish, Soundgarden, the Allman Brothers, Weezer, Pearl Jam, and Black Sabbath. The lineup features Ryan Marks on guitar, Max Aronov on bass, Ray DeLear on keys, and Brett Thomson on drums, locking into grooves that keep the energy flowing.

    Event website ↗
Friday, December 11 1 event
  • 7pm

    Junior Mack

    8 Greycourt Ave, Chester · verified Sep 13
    See details

    Meadow Blues welcomes Junior Mack to the stage for a live performance that blends blues, rock, and gospel. A self-taught guitarist and vocalist who has been performing since 1968, Junior has developed a distinctive style rooted in these traditions. He is the front man for Jaimoe’s Jasssz Band, a founding member of the Grammy-nominated Heritage Blues Orchestra, and has shared the stage with The Allman Brothers Band, Warren Haynes, Derek Trucks, Honeyboy Edwards, The Marshall Tucker Band, and Cyndi Lauper. His music has reached audiences across the United States, Europe, and India, and this appearance brings that experience to Chester, NY.

    Event website ↗

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