Calling all of our beer drinking, pizza eating, festival loving, stein holding friends, your services are needed!! Registration will begin at 6:30pm and competition starts at 8pm!

Get to Bennie’s , show off those muscles , and let’s see who can hold the beer stein the longest!!

Competitions will take place July 24th, August 7th, August 21st, and September 4th before the grand finale on the main stage, September 19th at the 45th Annual Belleville Oktoberfest - where you can win $500!! The top five from each week will go on to the Main Stage to compete.

Listen to the steal of a deal you get for your $20 entry fee to compete - you get your beer AND a coupon to redeem at Oktoberfest for an authentic, collectible drink ware item!! Plus, don’t forget you have a chance to win $500!

The Top 5 from each week will guarantee a spot on the main stage, September 19th! Where you can win it all! Cheers to that, am I right?!

Join us at the Public Square outside Sawdust & Glitter Saturday, August 8th in Downtown Belleville to kick off the school year and celebrate the end of summer!

Explore our curated vendors' creations, enjoy the back-to-school kids' fashion show & stop in to Sawdust & Glitter for all the Downtown DIY + Style.

This event grows each year & we thank you for celebrating along with us.

Craft with Your Canine Night!

Looking for a fun evening to spend with your pup? Join us for Craft with Your Canine Night hosted by Lazy Leash Events and proudly sponsored by The Barkery!

Mimosas, Margaritas and Music Walk assists in raising funds for all the entertainment at the 45th Annual Belleville Oktoberfest!

Purchase tickets now in person with cash at Bennie’s Pizza Pub or Venmo @BellevilleOktoberfest

$30 per person in advance or $35 day of per person

Walk starts and ticket pick up will be at Bennie’s Pizza Pub on 8/15/26 from 10am-12pm

Enjoy 10 4 oz samples or margaritas and mimosas while enjoying live music and helping raise funds for the Belleville Oktoberfest! Plus you will receive a $5 Beer Token Voucher to be redeemed during Belleville Oktoberfest September 18th and 19th.

Get ready for a night of raw, unapologetic outlaw country as Whey Jennings brings his electrifying Baptized by Fire Tour to Lincoln Theatre on August 16.

Born into country music royalty yet carving his own gritty path, Whey Jennings delivers a powerful blend of southern rock edge and outlaw soul

Calling all of our beer drinking, pizza eating, festival loving, stein holding friends, your services are needed!! Registration will begin at 6:30pm and competition starts at 8pm!

Get to Bennie’s , show off those muscles , and let’s see who can hold the beer stein the longest!!

Competitions will take place July 24th, August 7th, August 21st, and September 4th before the grand finale on the main stage, September 19th at the 45th Annual Belleville Oktoberfest - where you can win $500!! The top five from each week will go on to the Main Stage to compete.

Listen to the steal of a deal you get for your $20 entry fee to compete - you get your beer AND a coupon to redeem at Oktoberfest for an authentic, collectible drink ware item!! Plus, don’t forget you have a chance to win $500!

The Top 5 from each week will guarantee a spot on the main stage, September 19th! Where you can win it all! Cheers to that, am I right?!

Let’s Turn Back Time and experience Cher through Decades of music.
Coming from the St. Louis Metro area, these talented musicians capture the essence of Cher’s through music .
Cher played by Anne Kalaher exhibits Cher as you remember her through the years with her unique looks and sound.
It’s a must see show that will have you singing along and bring some nostalgia in your life.

Main Street bars and restaurants join forces to plan a fun day while raising money! Check out the event page for how to get involved!!!

Join us for a night of music, songs, stories and lots of laughs! Sean Dietrich is a columnist, humorist, multi-instrumentalist, and stand-up storyteller known for his commentary on life in the American South. Sean will be doing a meet & greet after the show complete with hugs, book signing & photographs. Merch will be available before & after the show. Doors open at 5:00 & the show starts at 6:00.

Calling all of our beer drinking, pizza eating, festival loving, stein holding friends, your services are needed!! Registration will begin at 6:30pm and competition starts at 8pm!

Get to Bennie’s , show off those muscles , and let’s see who can hold the beer stein the longest!!

Competitions will take place July 24th, August 7th, August 21st, and September 4th before the grand finale on the main stage, September 19th at the 45th Annual Belleville Oktoberfest - where you can win $500!! The top five from each week will go on to the Main Stage to compete.

Listen to the steal of a deal you get for your $20 entry fee to compete - you get your beer AND a coupon to redeem at Oktoberfest for an authentic, collectible drink ware item!! Plus, don’t forget you have a chance to win $500!

The Top 5 from each week will guarantee a spot on the main stage, September 19th! Where you can win it all! Cheers to that, am I right?!

Annual Labor Day Parade by Southwestern Illinois Central Labor Council

Welcome to another evening of Rocky Horror Picture Show mayhem as you enter Dr. Frank-N-Furter's residence at the Lincoln Theatre. It's astounding watching the cast of Flustered Mustard perform their shadow performance and lead the audience participation. Festivities start with a pre-show at 7:30pm of the history of Rocky Horror Picture Show. After that a virgin ceremony welcoming all first time viewers to the experience is performed before the movie starts.

All attendees will receive a prop bag. No outside props are allowed but feel free to dress as your favorite character. A portion of each ticket benefits Glow for Hope, suicide prevention.

Get ready to make history with us on Saturday, September 26, 2026, as we commemorate the 10th Anniversary of the Belleville Main Street Marathon and our Half Marathon being designated as the Road Runners Club of America Illinois State Championship Event!!!

Mark your calendars!

Fall is coming to Downtown Belleville, and we’re celebrating in the sweetest way!

Join us for Main Street Apple Fest on Saturday, September 26 for a day full of shopping, strolling, and all the cozy fall vibes.

Fresh apples & apple-inspired treats
Pumpkins & festive fall fun
Photo ops
Live music
Shop your favorite local small businesses
Cozy fall finds around every corner

Grab your family, invite your friends, and spend the day supporting the amazing small businesses that make our downtown so special. It’s the perfect way to kick off fall!

Celebration of the LGBTQIA+ Community

Join us for the 13th Annual Chili Chase 5K – Belleville’s favorite winter run!
Kick off your morning with a fun and festive race through the heart of Belleville. Whether you’re chasing a personal best, running for fitness, or simply soaking in the community spirit, this event is perfect for runners of all ages and abilities. Enjoy a lively atmosphere, great competition, and the chance to earn awards in multiple age categories. Plus, kids can join the Pepper Dash for their own medal and a big dose of fun!

Come and spend a spooky evening with the Witches of Belleville. Experience the potions and spells of our local shops, restaurants and bars.

Join area seniors 55+ as they shop + dine along Downtown Belleville’s Main Street Friday, October 16th from 10am - 1pm on Main Street Senior Day! Seniors will explore Main Street and enjoy an after-party at the PSOP building (hosted by Main Street Senior Day sponsors, PSOP & St. Clair County Office on Aging) full of fun & giveaways provided by our Belleville Main Street merchants.

Fur-ight Night is a free, dog-friendly Halloween event where pups and their people come together for a festive trunk-or-treat experience. Featuring costumes, treats, photo ops, and plenty of wagging tails, it’s a playful community event designed to celebrate the joy of dogs while connecting local pet lovers and businesses for a howlin’ good time.

VEGAN VIBES — Saturday, November 7th!

Join us in Downtown Belleville for a full day of plant-based fun!
All participating businesses will be offering delicious vegan food, drinks, and treats (where available) — plus vegan-friendly shopping and experiences.

Eat. Drink. Shop. Vibe.
Discover new flavors, support local spots, and celebrate all things vegan in the heart of downtown.

Downtown Belleville
Saturday, November 7th
Check participating businesses for their hours of operation.

The Art & Wine Walk returns Downtown Belleville Saturday, November 14th

Join us in celebration of one of the greatest pairings of all time - Art and Wine! Stroll downtown Belleville Main Street sampling wines, viewing artists' work, and listening to local musicians all while visiting Belleville Main Street merchant locations.

The 15th Annual Belleville Thanksgiving 5K Run and Kids Turkey Chase (In Person Race) will take place on Thanksgiving Day, Nov. 26, 2026, in Downtown Belleville Illinois at the Square. 

Join the community of Belleville for this annual parade when Santa comes to town. Sponsored by the Optimist Club of Belleville, this tradition began in 1952 and is the largest parade in Southern Illinois, featuring floats, marching bands, dance groups, and the arrival of Mr. & Mrs. Claus.

Think BIG & Shop SMALL November 28th for Small Business Saturday to support your favorite Downtown destinations. Visit our MERCHANTS page for a list of where to shop, eat, drink, and explore on Main Street this Small Business Saturday, throughout the Holiday season and everyday!

Experience the charm of Downtown Belleville during the holidays! Stroll Main Street and visit quaint shops, local restaurants and more while collecting over two dozen tasty Christmas cookies! Stick around and enjoy the German Christkindlmarkt, gingerbread displays, a horse-drawn trolley, the Santa house and other festivities!

Experience the charm of Downtown Belleville during the holidays! Stroll Main Street and visit quaint shops, local restaurants and more while collecting over two dozen tasty Christmas cookies! Stick around and enjoy the German Christkindlmarkt, gingerbread displays, a horse-drawn trolley, the Santa house and other festivities!

Make your gift list and check it twice! Take advantage of later shopping hours to finish your gifting needs. The holidays are magical on Main Street, and we can’t wait to meet you there!