Visitors Guide
What's Happening in Downstate Illinois September 26 - October 2

What's Happening in Downstate Illinois September 26 - October 2

Posted on 09/19/2022 by Emily Titsworth

Whether you’re looking for live music, a festival, marathon, or something family-friendly to bring the kids to, Downstate Illinois has something for everyone! Each week we highlight a few fun events within southwest, south central and southeast Illinois.  Our 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. For even more events, be sure to visit the Downstate Illinois Calendar of Events page here!




Fairfield Paint Out

Fairfield, IL

Tuesday, September 27, 2022 - Saturday, October 1, 2022 @ 9 a.m. - 10 p.m.

At Fairfield PaintOut, our mission is to invite artists - amateurs & professionals - to come to Fairfield, express their creative sides, and introduce our community to great art. Whether you’re a professional looking for new inspiration, an amateur hoping to learn a thing or two about art, simply interested in picking up new perspective of your home town and southern Illinois, Fairfield PaintOut is here to welcome you into the fold.



Open House & Ribbon Cutting

Highland Emporium, LLC, Highland, IL

Wednesday, September 28, 2022 @ 10 a.m. - 6 p.m.

Come join the fun at Highland's newest retail gem on The Square! Supporter of small businesses, award-winning local artists, local specialty food artisans, furniture and home decor refinishing, local CBD products, hand-made soaps, blown glass and so much more! FOOD TASTINGS from our vendors begins at Noon along with the ribbon cutting ceremony and will be available until approximately 2 p.m.



Wine for Whiskers

The Weingarten, Belleville, IL

Thursday, September 29, 2022 @ 6 p.m. - 8 p.m.

Belleville Area Humane Society (BAHS) will host its annual Wine for Whiskers on September 29, 2022 at the Weingarten in Belleville from 6:00 pm until 9:00 pm. Wine for Whiskers is sure to sell out, so act quickly and don't miss your chance. Tickets are $60 in advance and available online and all proceeds benefit the Belleville Area Humane Society.



NHRA Midwest Nationals

World Wide Technology Raceway, Madison, IL

Friday, September 30, 2022 - Sunday, October 2, 2022 @ 10:30 a.m. - 9:15 p.m.

NHRA Midwest Nationals will be returning to World Wide Technology Raceway on Sept. 30 – Oct. 2, 2022 for a weekend filled with action-packed, nitro-fueled drag racing that will shake you to your core. You won’t want to miss it!

Heath Harvest Fest

Robinson, IL

Friday, September 30, 2022 - Saturday, October 1, 2022 @ 3 p.m.

Located on the square in Robinson. Celebrating the delicious Heath Candy Bar, created in 1928 by Heath Brothers Confectionary in Robinson. Features Friday night entertainment, street dance, and car show, and Saturday craft show, live entertainment, toffee bake-off, and parade, capped off by a free chili supper.


Stubborn German Brewing Company, Waterloo, IL 

Friday, September 30, 2022 - Saturday, October 1, 2022 @ 3 p.m. - 11 p.m.

Time to celebrate Oktoberfest at Stubborn German in Waterloo! Drink German Bier while enjoying German Bands in a German town!

The Vandoliers

Carmi VFW, Carmi, IL

Whetstone Oil and The Taco Factory present The Vandoliers from DFW Texas @ Carmi IL on Friday September 30th 2022!

Sweet N' Spooky Gingerbread Class

Nichols Community Center, Belleville, IL

Friday, September 30, 2022 @ 6:30 p.m.

Learn how to create your own gingerbread haunted house with the experts from the Belleville Gingerbread Contest Committee. Only $15 per family!



2022 Fall Fest

Keyes Park, Du Quoin, IL

Saturday, October 1, 2022 @ 8 a.m. - 5 p.m.

Come join us for a full day of fun with Craft and Merchandise vendors, Live Music, Food Trucks, Kids Corner, a Chili Cook Off, Corn Hole Tournament, 3 on 3 Basketball Tournament.

Annual White Squirrel Count

Olney, IL

Saturday, October 1, 2022 @ 8 a.m. - 4 p.m.

The annual squirrel count takes place on the first three Saturdays in October. 

Apple Day in Greenville

Downtown Greenville, Greenville, IL

Saturday, October 1, 2022 @ 9 a.m. - 2 p.m.

Join the City of Greenville, Bond County Recovery Council, Bond County Cruise-Ins, and Lost & Found for a jam-packed mega-event on Saturday, October 1 from 9:00 AM to 2:00 PM! The event includes food trucks/booths, kids activities, inflatables, carnival games, special speakers, a car show, pumpkin decorating, the Greenville Farmers Market, a chili cookoff, live music, face painting, a special visit from storybook characters, and SO MUCH MORE!

Lebanon Fall Festival

Downtown Lebanon, Lebanon, IL

Saturday, October 1, 2022 @ 9 a.m. - 4 p.m.

Annual Fall Festival with lots of fun, food, and great gift ideas. Plan on spending the day with friends, family and great music and friendly people!

Columbia Scarecrow Crawl

Historic Main Street, Columbia, IL

Saturday, October 1, 2022 - Monday, October 31, 2022 @ 10 a.m. - 9 p.m.

Quickly becoming a community loved event, the Columbia's Scarecrow Crawl planned for October 1 through October 31 showcases over 50 scarecrows! Come take a stroll on Historic Main Street to see all the amazing entries created by individuals, schools, businesses, organizations, churches and more.

Freeburg Fall Festival & Chili Cookoff

Freeburg Village Park, Freeburg, IL

Saturday, October 1, 2022 @ 11 a.m. - 7 p.m.

The Freeburg Fall Festival & Chili Cook Off is a great family friendly event that supports Local Not for Profit Groups.

2022 Metro East Pride Fest

West Main Street, Belleville, IL

Saturday, October 1, 2022 @ Noon - 10 p.m.

Family-friendly festival celebrating the LGBTQIA+ Community.

Wabash Valley Wine & Art Festival

123 S Main St. Palestine, IL

Saturday, October 1, 2022 - Sunday, October 2, 2022 @ Noon - 5 p.m.

The Festival is held the first weekend of October each year and brings together wineries and artists from throughout the region.

Belleville Indie Market: After Dark

Seven Belleville, Belleville, IL

Saturday, October 1, 2022 @ 5 p.m. - 9 p.m.

Shop over 35 local artists and creative entrepreneurs for one night only at an event you’re not going to want to miss.



TURF 3rd Annual Pink 5k

Turf Bar and Banquet, Breese, IL

Sunday, October 2, 2022 @ Noon

Join us at Turf Bar and Banquet for a family friendly fun run to support breast cancer. We will be raising money for the American Cancer Society as well as the Highland Area Resource Team.

Columbia FestiFall

Metter Park, Columbia, IL

Sunday, October 2, 2022 @ 1 p.m. - 6 p.m.

Celebrate fall with great food (including authentic German potato pancakes), beer and wine, unique merchandise vendors and a HUGE kid zone! 

Harvest Festival

Hidden Lake Winery, Aviston, IL

Sunday, October 2, 2022 @ 2 p.m. - 6 p.m.

Join us for our annual Harvest Festival! Great, local vendors, live music, wine, and great food!


To submit an event to be published on the Downstate Illinois website, click here!


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