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Events in Downstate Illinois

Events in Downstate Illinois

Find Your Next Event

Whether you’re looking for a festival, marathon or something family-friendly to bring the kids to, Downstate Illinois has something for everyone. The region hosts over 900 events each year, and we pride ourselves on providing the most accurate event information so that you don’t miss a thing.

What are you waiting for? Explore our Event Calendar to find the perfect entertainment for you and your family during your visit.

Please use the color-coded map for reference.

  • Western Region (Orange) – Close to St. Louis, MO
  • Central Region (Blue) – Close to Springfield, IL
  • Eastern Region (Yellow) – Close to Terre Haute, IN

The Million Race 1, 2, 3, 4

 September 16, 2025 - September 20, 2025
World Wide Technology Raceway
Madison, IL

Highland Farmer's Market

 September 16, 2025
Highland Square
Highland, IL

Highland Thursday Night Live Concert Series

 September 18, 2025
Downtown Square
Highland, IL

Carlyle City Wide Yard Sales

 September 19, 2025 - September 20, 2025
City Wide
Carlyle, IL

Marshall Autumn Fest

 September 19, 2025 - September 21, 2025
Downtown Marshall
Marshall, IL

Whale of a Sail Regatta

 September 19, 2025 - September 21, 2025
Carlyle Lake
Carlyle, IL

Farmers Market at Courthouse Square

 September 20, 2025
Downtown Square
Charleston, IL

Artisan's Fall Festival

 September 20, 2025
Edwards County Courthouse
Albion, IL

Tour de Tilden Bike Ride

 September 20, 2025
Tilden City Park
Tilden, IL

Vine Street Market

 September 20, 2025
O'Fallon Station
O'Fallon, IL

Saturday Morning Market at Paper Moon

September 20, 2025
217 E Main Mascoutah
Mascoutah, IL

Street Art Festival

 September 20, 2025
Highland Square
Highland, IL

Albion Fall Artisan's Fair

 September 20, 2025
Albion Courthouse Square
Albion, IL

Music at the Park: Bad Company Tribute

 September 20, 2025
Merchants Park Mount Carmel, IL
Mount Carmel, IL

Edwards County Paint Out

 September 22, 2025
Edwards County Fairgrounds
Albion, IL

Highland Farmer's Market

 September 23, 2025
Highland Square
Highland, IL

Highland Thursday Night Live Concert Series

 September 25, 2025
Downtown Square
Highland, IL

Mattoon Flea Market

 September 26, 2025 - September 28, 2025
Cross County Mall
Mattoon, IL

NHRA Midwest Nationals

 September 26, 2025 - September 28, 2025
World Wide Technology Raceway
Madison, IL

Carlyle Farmers Market

 September 26, 2025
Carlyle VFW
Carlyle, IL

Apple Butter Peeling and Stirring

 September 26, 2025 - September 27, 2025
The Rock Mill
Maeystown, IL

New Baden Farmers Market

 September 27, 2025
New Baden Village Park
New Baden, IL

Vine Street Market

 September 27, 2025
O'Fallon Station
O'Fallon, IL

Annual Fall Festival

September 27, 2025
Olney City Park
Olney, IL

Saturday Morning Market at Paper Moon

September 27, 2025
217 E Main Mascoutah
Mascoutah, IL

Harvest Frolic

 September 27, 2025 - September 28, 2025
Lincoln Log Cabin State Historic Site
Lerna, IL

Hops & Hogs Brew-B-Q

 September 27, 2025
Downtown
Red Bud, IL

Music at the Park: Fleetwood to the Max-Fleetwood Tribute Band

 September 27, 2025
Merchants Park Mount Carmel, IL
Mount Carmel, IL

Highland Farmer's Market

 September 30, 2025
Highland Square
Highland, IL

Heath Harvest Festival

 October 3, 2025 - October 4, 2025
Downtown
Robinson, IL

Mount Carmel City Wide Yard Sales

 October 3, 2025 - October 4, 2025
City Wide
Mount Carmel, IL

Grizzlies Rodeo

 October 3, 2025 - October 4, 2025
Grizzlies Ballpark
Sauget, IL

Budding Naturalist

 October 3, 2025
Douglas-Hart Nature Center
Mattoon, IL

Campin' and Cookin' BBQ Competition

 October 3, 2025 - October 5, 2025
Grayville KOA
Grayville, IL

Stubbornfest

October 3, 2025 - October 4, 2025
Stubborn German Brewing Company
Waterloo, IL

Lebanon Fall Festival

 October 4, 2025
Downtown Lebanon
Lebanon, IL

Metro East Pride Fest

 October 4, 2025
West Main Street
Belleville, IL

Vine Street Market

 October 4, 2025
O'Fallon Station
O'Fallon, IL

Off The Square Vintage Market

 October 4, 2025
Off The Square
Lawrenceville, IL

Saturday Morning Market at Paper Moon

October 4, 2025
217 E Main Mascoutah
Mascoutah, IL

Wabash Valley Wine and Art Festival

 October 4, 2025 - October 5, 2025
Main Street in Palestine, IL
Palestine, IL

Fall Food Truck Frenzy

 October 4, 2025
Downtown
Marshall, IL

District Frights

 October 4, 2025
Downtown O'Fallon
O'Fallon, IL

Boo on the Bricks

 October 5, 2025
Edwards County Courthouse
Albion, IL

Columbia FestiFall

 October 5, 2025
Metter Park Columbia IL
Columbia, IL

Scarecrow Crawl

 October 6, 2025 - October 31, 2025
Historic Main Street
Columbia, IL

Columbia Witches Ghoulish Night Out

 October 9, 2025
Main Street
Columbia, IL

41st Annual Belleville Chili Cook-Off

 October 10, 2025 - October 11, 2025
Downtown
Belleville, IL

Midnight Madness #8 Theme: Fall Festival

 October 10, 2025
World Wide Technology Raceway
Madison, IL

Vandalia Witches Night Out

 October 10, 2025 - October 11, 2025
This-n-That
Vandalia, IL

Vandalia Farmers Market

 October 11, 2025
Next to Vandalia Statehouse
Vandalia, IL

Vine Street Market

 October 11, 2025
O'Fallon Station
O'Fallon, IL

Pumpkinfest - Waterloo

 October 11, 2025
Courthouse Square
Waterloo, IL

Saturday Morning Market at Paper Moon

October 11, 2025
217 E Main Mascoutah
Mascoutah, IL

Chili Cook-Off

 October 11, 2025
N Hanover Street
Okawville, IL

VP Racing Lubricants No-time Streetcar Showdown #7

 October 11, 2025
World Wide Technology Raceway
Madison, IL

Maeystown Oktoberfest

 October 12, 2025
Downtown Maeystown, IL
Maeystown, IL

Waterloo Witches Night Out

October 16, 2025
Downtown Waterloo
Waterloo, IL

CHESTER FALL FESTIVAL 2025

 October 16, 2025 - October 19, 2025
COLE MEMORIAL PARK
Chester, IL


Downstate Illinois Events

Downstate Illinois Events

Explore Our Event Calendar
Whether you’re looking for a festival, marathon or something family-friendly to bring the kids to, Downstate Illinois has something for everyone. The region hosts over 900 events each year, and we pride ourselves on providing the most accurate event information so that you don’t miss a thing.
Travel Ideas

Travel Ideas

Check Out Our Blog
From outdoor recreation and adventure to foodies and family fun, we have the trip ideas to plan the perfect vacation.
Road Trip Itineraries

Road Trip Itineraries

22 Counties made for Road Trips
Downstate Illinois was made for road trips! With the help of our road trip itineraries, you can discover all that our 22 counties have to offer — from family fun to outdoor adventures and shopping sprees. 
Check out our calendar of events!
The Million Race 1, 2, 3, 4

The Million Race 1, 2, 3, 4

 September 16, 2025 - September 20, 2025 @ 12:00 PM - 12:00 PM
World Wide Technology Raceway | Madison, IL
Highland Thursday Night Live Concert Series

Highland Thursday Night Live Concert Series

 September 18, 2025 @ 7:00 PM - 9:00 PM
Downtown Square | Highland, IL
Carlyle City Wide Yard Sales

Carlyle City Wide Yard Sales

 September 19, 2025 - September 20, 2025 @ 7:00 AM - 4:00 PM
City Wide | Carlyle, IL

View Entire Events Calendar

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