Events in Greenville, IL

This seasonal marketplace celebrates community, gathering local growers, makers, food producers, and community organizations in the center of Highland. It offers a welcoming setting for connection and a chance to explore what participants are sharing.

A community-focused evening dedicated to appreciating the people who keep everyone safe and supported every day. On the first Thursday of each month, First Responders' Night welcomes Law Enforcement, Fire, Paramedics, Dispatchers, Corrections officers, and Veterans. Eligible guests receive a free game for themselves and their families, along with 15% off snacks, soda, and additional games.

Enjoy a live performance by Jaimi Keys on the patio.

Plants With Peradotti brings a diverse selection of healthy plants to the Bond County Farmers Market in Greenville, IL, with a special nod to the 250th anniversary of the United States. Browse favorites such as alocasias, monsteras, philodendrons, and hoyas, along with other varieties. Quantities of specific plants are limited, so particular finds may sell out. In honor of the Fourth of July, the booth features notable price reductions across the inventory. Look for the setup in front of Abstract & Title Insurance, just northeast of the courthouse, and discover something green to brighten your space.

Shop the Saturday sale at Holly’s House of Hope, where clients have carefully sorted, labeled, and hung a refreshed mix of gently used and new items. Explore clothing in a wide range of sizes along with various miscellaneous finds. This is a thrift store that welcomes all shoppers. Payments are accepted by cash or card, with a small fee for card transactions. Donations will also be accepted during the sale.

Spencer McDole brings a broad mix of favorites to Copper Dock, spanning decades with songs by artists such as Tom Petty, The Beatles, John Prine, Johnny Cash, Sublime, Red Hot Chili Peppers, Jim Croce, Stone Temple Pilots, The Cure, Jason Isbell, Elvis, and more.

Spencer McDole performs a live set on the patio.

BFDA returns with its third annual trivia night, this time Halloween themed with festive decorations, spooky fun, and a costume contest honoring the best dressed team. The previous two years sold out, so early table reservations are encouraged. To reserve a table, call or text (618) 210-1157.

A special guest opener is in the works to pair original music with familiar cover tunes. If plans align, Rock Artillery Fallback, the band that includes Mr. Smith from Pocahontas Elementary, will start the night with a set of all original songs. After their set, EXIT 36 will take the stage with a lineup of covers. The focus is on spotlighting local musicians who create and perform their own material, offering a mix of originals and covers in one show.

A favorite place to play sets the scene for a lively party. Expect upbeat energy and a fun, celebratory vibe.

A welcoming, judgment-free group where people facing mental health challenges can connect, share experiences, and find encouragement. Conversations focus on emotional support, practical coping tools, stress reduction, and overall well-being through open dialogue and peer-to-peer connection. Attendees can talk about current hurdles, celebrate progress, and set personal goals while practicing healthy strategies and strengthening their support network. This gathering is suited for individuals experiencing anxiety, depression, stress, life changes, or other mental health concerns who value regular support and meaningful connection.

This 5K and 10K race organized by the Bo Arvin Memorial Foundation honors Bo Arvin and the qualities that endeared him to many, including kindness, loyalty, humor, respect, faith, and courage. It raises awareness of pediatric cancer and the gap in funding for research toward improved treatments and a cure. Fundraising from the event benefits The Children's Cancer Therapy Development Institute and the Bo Arvin Memorial Foundation.

Everyone is welcome at this vaccine and microchip clinic. Payment is accepted by cash or check only. For any questions, please email info@mehs.org.

Downtown Vandalia turns into a lively community marketplace on 5th Street beside City Hall, where local growers, bakers, and makers share the best of the season. Find farm-fresh produce, homemade baked goods, meats and other farm products, along with a variety of specialty foods. On the same day, the Vandalia Picker’s Market sets up along Gallatin Street with vintage pieces, antiques, collectibles, and unique finds, creating a two-market experience in one downtown stroll. Nearby shops and restaurants add even more to explore. Throughout the season, look for themed markets, family-friendly activities, and special celebrations that highlight local agriculture, support small businesses, and recognize America’s 250th anniversary.

Enjoy a day filled with music, food, and games while exploring vendors. The highlight is Goat Yoga, adding a playful centerpiece to the celebration.

An author will visit the National Road Interpretive Center for a talk and book signing. Books will be available on site, and admission is free. Tours of the Interpretive Center will be offered, with the option to extend if needed. For more information, call 618-283-9380.

Foster Kairos leads a story hour at The Freckled Page featuring stories that highlight good mental and emotional health for children. The reading time centers on themes that support kids' well being.

Route 66: The Haunted Hundred turns the Mother Road into a seasonal adventure as part of The Last 100 Miles Festival, a multi community celebration honoring 100 years of travel along the final stretch of the highway in Illinois. Throughout the weekend, travelers make their way from stop to stop to collect exclusive trading cards from participating communities and businesses, building a full set while discovering classic Route 66 sights. At the Pink Elephant campus, the atmosphere blends family fun, fall activities, and spooky highway lore. Saturday includes complimentary bounce houses, a gentle haunted experience created for younger guests that supports the Livingston Park Association Holiday Basket program, a flashlight egg hunt for ages 0 to 20, and the Area 66 Haunted School for those ready for a full scare. Sunday brings more free bounce houses, a haunted vendors market with Halloween creations, fall goods, crafts, and Route 66 themed items from local makers, plus free horse drawn carriage rides. While exploring the campus, visitors can browse the Pink Elephant Antique Mall, grab a bite at Twistee Treat Diner, satisfy a sweet tooth at Mother Road Fudge and Candy Shop, and snap photos with roadside icons. An exclusive trading card tied to this stop is available as part of the festival road trip.

TGNY Acoustic returns to Copper Dock with a live acoustic set performed under the gazebo.

Bike Night takes place at High Octane Bar & Lounge on the third Thursday of each month from April through October. Expect food trucks, a DJ, a 50/50 drawing, attendance prizes, and drink specials, along with blacktop parking for bikes. Friends are welcome and the vibe is leave-the-attitude-at-home.

An early autumn gathering at The Greenhouse pairs wine with a relaxed mix of acoustic classics. Expect musical jams, the listening kind rather than something from a jar.

Curt Copeland returns to The Blue Note lounge at Canton Inn in Schram City for an evening of live music. Enjoy dinner alongside a selection of adult beverages while the set unfolds in this cozy lounge setting.

UNBROKEN performs rock music at Bretz Wildlife Winery in Carlyle. Food and drinks will be available.

Tres Acousticans + Paul are back at the square in Highland for the annual Moose Chili Cook-off and car show. They will be on site as part of the event.

At Hard Dog Cafe, Tom O DJ will spin requests for songs found on the internet. Karaoke should be available. If you can find a track on your smartphone, he can play it.

Wicked Mojo brings a high energy show to Bretz Wildlife Winery in Carlyle with favorites that span the 80s to today’s hits. The goal is to get everyone dancing, with cold drinks and an upbeat soundtrack keeping the vibe going all night.

Settle in at the dock for live tunes and beverages in a relaxed setting.

A complimentary, in-person seminar presented by Sheila Riggs, REALTOR, offers practical guidance for homeowners considering a sale within the next year or already preparing. The session walks through the full journey from listing to closing, explains how to select the right agent, outlines effective marketing approaches, and clarifies seller rights such as contracts and disclosures. It also sets expectations for showings, offers, inspections, and the steps that follow. Attendees can expect to leave with a clear plan and greater confidence for the selling process. Seating is limited.

Venture into Vandalia at sundown for a 5K without timing that blends small-town charm with a touch of spooky fun. Framed as a signature Fayette County event, the route starts in the heart of town, heads toward the quiet edge of the cemetery, then returns in the fading light. Costumes and glow gear help set the scene, and the lively Spirits Run energy carries through from beginning to end.

Costumes set the tone at The Corner Keg Pub in Highland for a Classic Crush night. Attendees are encouraged to wear their best outfits and enjoy a festive party at a favorite local bar.

Celebrate Halloween with a festive evening featuring a meal, music, and time to mingle. The costume contest offers a $100 prize for first place. Reservations are highly recommended.

Psychedelic Symphony brings a Halloween performance to Hard Dog Cafe, setting a playful, spooky vibe with groovy ghoul energy.

Dark Horse brings its third annual Halloween party to Corner Keg in Highland. The night features music, prizes, and plenty of creative costumes.

The Hawg Diner in Vandalia, Illinois sets the stage for a rocking good time.

Harvest Drive appears at The KeySpot for an afternoon that brings together fun, music, food, and drinks. Everything comes together in one easygoing gathering.

The Highland Civic Woman’s Club hosts its monthly meeting at Hope Lutheran Church Highland, with conversation centered on plans for a fun and meaningful fall. Expect collaborative discussion on upcoming initiatives, creative ways to welcome new members, and ideas to expand the club’s impact in the community. Participants can enter the monthly purse raffle for a chance to win a designer bag, and anyone who brings a guest will be entered into a special drawing. The Highland Civic Woman’s Club is a local service organization dedicated to strengthening the community through volunteerism, education, and civic engagement. Women of all ages are welcome, and first-time visitors attend free.

Holly’s House of Hope is holding a Saturday Sale at its thrift store, offering new and gently used inventory that has been carefully prepared by clients who sorted, labeled, and hung items for easy browsing. Expect clothing in many sizes along with a variety of miscellaneous items, and all shoppers are welcome. Payment is accepted by cash or card, with a small fee for card transactions. Donations will be accepted during the sale.

Soup on the Square returns for its second year as a welcoming community gathering centered on a complimentary warm meal and time together. Families and neighbors can enjoy bounce houses, live music, food trucks, a variety of vendors, a vendor area for kids, and activities for all ages. A coat and blanket swap invites attendees to donate items or pick up something they need from the donation tent. Bringing something is optional, and anyone may take an item that feels right. Proceeds help fund next year's Soup on the Square, and donations are appreciated but not required. Hosted by Highland Community Closet, an organization that provides essentials to those in need.

Returning due to popular demand, ShortMist brings a lively night packed with music and fun.

The 2026 season begins with the lights being switched on, signaling the start of the celebrations. Details about additional scheduled events will be shared in the months ahead.

Unbroken performs live at The KeySpot for a night of rock music.

Sunday Funday at Bretz features music, tasty food, and a fun atmosphere.

The Fall Artisan Market returns to Highland High School with its largest lineup yet. It showcases work from more than 100 local crafters, artists, and makers and supports the entire district music program.

A return to a favorite hangout sets the scene for an evening with no cover charge, tasty food, friendly company, gaming, and plenty of music. A selection of spirits and liquors is available, bringing everything for a fun night in one place.

This annual lighted parade from the Chamber of Commerce honors 250 years of America with a Star Spangled Christmas theme at Highland Square. Illuminated entries will showcase patriotic decorations, and the procession concludes on the square with a lighting ceremony. Highland Machine is recognized as the Christmas sponsor. Additional information, including entry forms, the parade route, and Santa’s hours, will be available on the event website.

Small Business Saturday in Highland brings a cheerful twist to shopping local. Throughout the day, Chamber representatives will visit neighborhood shops and reward customers who are spotted supporting small businesses with a $50 certificate from the Chamber. Choose local this season and watch for announcements about additional activities and deals happening around Highland for Small Business Saturday.

ShortMist brings live music to The KeySpot, with food available and a relaxed, social vibe. It offers a way to unwind before the seasonal bustle.

Explore a mix of new items and gently used finds at this thrift store sale, with clothing available in a wide range of sizes along with assorted miscellaneous goods. Clients have carefully sorted, labeled, and hung the inventory to make browsing simple. All shoppers are welcome. Cash is accepted, and card payments are also accepted with a small fee applied. Donations will be accepted during the event.

Hosted by the Highland Chamber of Commerce, this free Cookie Crumb Trail celebrates shopping local with sweet treats along the way. Pick up a map to get started, then visit Cookie Trail businesses where a cookie to sample and a recipe card to take home are waiting. Each stop will check off its name on your map. When every stop is marked, turn in your completed map to the Highland Chamber office for entry into a drawing. Two lucky winners will each receive a $75 Chamber Gift Certificate that can be used at many local businesses. The first 100 participants receive an event tote, one per family. More details to come.

Exit 36 channels the spirit of 1994 grunge at The Old Mill. Expect a powerful set of classic tracks delivered with raw, high energy for a hard hitting show.