Crazy Train - America's Ozzy Tribute
Oct
30
7:30 PM19:30

Crazy Train - America's Ozzy Tribute

Crazy Train™ is the ultimate touring Ozzy Osbourne Tribute show, Hosted by vinny cormier, the best Ozzy impersonator you can get, and supported by a berklee level crew, including his son dylan on guitar. crazy train delivers a captivating show unlike no other tribute, musically and visually. This show is packed with Special Effects and "wow" moments you won't forget! crazy train plays every show like it is LIVE AND LOUD 1993! crazy train rolls over all of the prince of darkness' noteworthy hits anywhere from sabbath to patient #9

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Vegan Vibes
Nov
1
9:00 AM09:00

Vegan Vibes

VEGAN VIBES — Saturday, November 1st!

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 1st
Check participating businesses for their hours of operation.

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Bling-a-Book Open Night @ Sawdust & Glitter
Nov
6
6:00 PM18:00

Bling-a-Book Open Night @ Sawdust & Glitter

BLING A BOOK NIGHT!
Grab your favorite book (or journal) and let’s make it shine!

Join us Wednesday, Nov 5th from 6–8 PM at Sawdust & Glitter for a night full of sparkle, snacks, and fun. We’ll be rhinestoning book covers — because reading is better when it’s blinged out!

Bring your friends, drinks, snacks, and even the kiddos — everyone’s welcome for this crafty, glittery good time.

Let’s do something a little different and add some sparkle to our shelves!

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Art & Wine Walk
Nov
8
3:00 PM15:00

Art & Wine Walk

The Art & Wine Walk returns Downtown Belleville Saturday, November 8th

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

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Pink Friday on Main Street
Nov
21
10:00 AM10:00

Pink Friday on Main Street

Shop Belleville’s East & West Main Street retailers as we kick off the holiday season in style!
Clothing • Stocking Stuffers • Vintage Finds • Home Décor • Books • Crafts • Jewelry & More

Get a head start on your holiday shopping while supporting local favorites all along Main Street!

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Turkey Trot and Turkey  Chase
Nov
27
7:00 AM07:00

Turkey Trot and Turkey Chase

The 15th Annual Belleville Thanksgiving 5K Run and Kids Turkey Chase (In Person Race) will take place on Thanksgiving Day, Nov. 27, 2025, in Downtown Belleville Illinois at the Square.  Race Day Registration and Packet Pickup at 7:00 am. with the race starting at 8 am.  

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Santa Claus Parade
Nov
28
10:00 AM10:00

Santa Claus Parade

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.

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Small Business Saturday
Nov
29
7:00 AM07:00

Small Business Saturday

Think BIG & Shop SMALL November 29th 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!

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Downtown Cookie Stroll
Dec
12
10:00 AM10:00

Downtown Cookie Stroll

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!

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Downtown Cookie Stroll
Dec
13
10:00 AM10:00

Downtown Cookie Stroll

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!

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Main Street Senior Day: Halloween Edition
Oct
17
10:00 AM10:00

Main Street Senior Day: Halloween Edition

Join area seniors 55+ as they shop + dine along Downtown Belleville’s Main Street Friday, October 20th 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.

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Belleville Chili Cook-off
Oct
10
to Oct 11

Belleville Chili Cook-off

  • BELLEVILLE PUBLIC SQUARE (map)
  • Google Calendar ICS

Hosted by the Greater Belleville Chamber of Commerce, the Annual Chili Cook-off has featured the culinary creations of individuals, local organizations, and area businesses for more than 40 years! What started with just a few vendors on one block of East Main Street in downtown Belleville has now grown to more than 60 vendors and is one of the largest festivals in Belleville!  

https://www.bellevillechili.com/

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Spooky Market Day
Oct
5
3:00 PM15:00

Spooky Market Day

Spooky Market Day & Halo Anniversary Party! What’s Happening:
• Spooky ghost photo ops & treasures galore at The Vintage Market
• Face painting by Green Root Gallery
• Charm bar by Ellie James
• Surprises & goodies from Belleville Books
• Halo Boutique’s anniversary celebration: sales, giveaways & fresh finds
• Sweet treats by Sugar High

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Belleville Main Street Marathon and Half Marathon
Sep
27
7:00 AM07:00

Belleville Main Street Marathon and Half Marathon

Come run this hometown marathon and half marathon on a portion of America’s Longest Main Street right here in historic Belleville, IL, on the last Saturday in September (Sept. 27th).The Belleville Main Street Marathon and Half Marathon are great for both novice and seasoned runners and has the amenities of a top-notch race, including enthusiastic volunteers along Main Street, great course support, awesome post-race party, event shirts, and an affordable registration fee!

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Cher Tribute
Sep
5
8:00 PM20:00

Cher Tribute

Experience the decades of Cher through an unforgettable tribute brought to life by the mesmerizing Anne Kalaher. From her iconic looks to that unmistakable voice, relive the power and passion that Cher has shared with the world. Coming from the St. Louis Metro area, these talented musicians capture every essence that makes Cher legendary. Sing along, feel the nostalgia, and let the music empower your soul!

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Downtown Belleville Pickle Palooza
Jul
19
10:00 AM10:00

Downtown Belleville Pickle Palooza

Not just any dill, a big dill! It’s time to celebrate a fan favorite - PICKLES!

We are teaming up to bring you amazing food and drinks; and we are here to get creative. Save the date, and tune in the official Facebook event as your favorite Main Street businesses showcase what we are sure will pickle your fancy!

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Christmas in July on Main Street
Jul
12
10:00 AM10:00

Christmas in July on Main Street

Get Ready to Sleigh the Sales – Christmas in July is Here! Join us for a holly-jolly shopping spree with exclusive deals, festive fun, and mid-year cheer! Unwrap incredible discounts, limited-time offers, and surprise giveaways – just like Christmas morning, but with summer vibes.

Santa will be at Sugar High at 10am and be surfing his way to Halo Boutique and Rusty Gem Vintage Market!

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Craft Beer Walk
Jun
28
3:00 PM15:00

Craft Beer Walk

Join us on Saturday June 28h from 3:00-7:00 pm for our annual Craft Beer Walk in Downtown Belleville. Hosting a few hundred attendees each year, the Craft Beer Walk offers attendees a beautiful evening exploring Downtown Belleville while sampling the best beer selections from over 25 regional breweries.

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Senior Day
May
30
10:00 AM10:00

Senior Day

Join area seniors 55+ as they shop + dine along Downtown Belleville’s Main Street Friday, May 30th 10am - 1pm on Senior Day! Seniors will explore Main Street and enjoy an after-party at the PSOP building (hosted by Senior Day sponsors, PSOP & St. Clair County Office on Aging) full of fun & giveaways provided by our Belleville Main Street merchants.

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Memorial Day Parade
May
26
10:00 AM10:00

Memorial Day Parade

We invite you to join us for the annual Belleville Memorial Day Parade on May 26, 2025. It is our hope that numerous residents will gather along the parade route and that various organizations will participate in paying tribute to the individuals who have given their lives to protect our freedoms. To participate in the parade, kindly visit our city's website via the link provided to obtain an entry form, parade guidelines, and map.

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Art on the Square
May
16
to May 18

Art on the Square

  • Veteran's Memorial Fountain (map)
  • Google Calendar ICS

Join us for an unforgettable weekend featuring 109 incredible artists, 11 diverse art categories, and talent from 27 states, plus 1 artist from outside the U.S. Let the countdown to creativity begin!

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