Every chili cook-off team has to make at least 10 gallons. That rule is on the Mascoutah Chamber's Fall Festival page, along with others: the chili has to be ready to serve at 11 a.m., it is served the way it was made, and crackers are the only allowed topping. The Chamber says as many as 20 entries will compete. If every team sends at least the minimum, that could be 200 gallons of chili on Main Street, all served in a three-hour window.
That window, plus two other set times, shapes the whole day on Saturday, October 17. The festival runs from 10 a.m. to 4 p.m. at Main and Railway. Most of what matters happens in just a few blocks around City Hall, and the rest of the day works around three times: 11:00, 1:15 and 3:00.
The three times that set the day
The Chamber lists more than 120 craft vendors. It also describes a car show with more than 160 classic and custom cars and trucks, entertainment on two stages, a free children's petting zoo and carriage rides. That's a lot to cover in six hours. Only a few things are fixed to a specific time, though, and they are the ones to plan around.
| Time | What happens | Where |
|---|---|---|
| 10:00 a.m. | Festival opens, vendors and car show | Downtown, Main & Railway |
| 11:00 a.m. to 2:00 p.m. | Chili Cook-Off tasting | Downtown chili stands |
| 1:15 to 1:45 p.m. | Fall Fest Storytime on Main Street | 3 West Main St. |
| 3:00 p.m. | Chili winners announced | Bandstand, parking lot across from City Hall |
| 4:00 p.m. | Festival closes | Downtown |
The chili window closes at 2:00, an hour before the results. Anyone hoping to taste the winner before it's named has to get there before the pots run dry. Stands supply cups, spoons and a ballot box, and they are not allowed to hand out drinks. Plan on getting your drink somewhere else.
There are four awards: People's Choice, decided by those ballot boxes, plus 1st, 2nd and 3rd place chosen by judges. The Chamber puts the prize pool at $1,600. Cook-off entries were due October 2. The Chamber's page also says it is not taking any more vendors. The lineup is set, so this year's festival is for showing up.
Where the 1:15 storytime fits
The Mascoutah Public Library's listing puts a free Fall Fest Storytime at 3 West Main St. from 1:15 to 1:45 p.m., and the listing notes the Chamber runs it. It lands in the middle of the chili window, so families with young kids can taste first, stop for storytime, and still be back in time for the 3:00 results.
That gives the afternoon a natural route for a family with little kids:
- Arrive near 11:00 and taste chili while every stand still has some.
- Fill the late morning with the petting zoo, carriage rides and cars.
- Be at 3 West Main by 1:15 for storytime.
- Spend the next hour at the vendor booths or the two stages.
- End at the bandstand across from City Hall at 3:00.
The Mascoutah Visitor's Center at 200 East Main St. is the Chamber's office, and it's where cook-off entries had to be paid in person. It's a good place to ask a question in person on festival day.
Lunch on the same blocks as the festival
The chili ends at 2:00, but the festival runs until 4:00, and most of downtown's restaurants sit on the same stretch of Main Street. These spots appear in the City of Mascoutah's business directory or the Chamber's member directory. Hours on a busy festival day may not match the usual ones.
- Camino Real, 9 W. Main St.
- Hawkin's Burger Bar at The Vault, 28 E. Main St., listed as a bar and restaurant with a kitchen
- El Sombrero Mexican Restaurant, 215 W. Main St.
- Joe's Pizza and Pasta, 215 E. Main St.
- Skootr's Restaurant and Bar, 323 E. Main St.
Two more are a short walk off Main. Twin Dragons, a Chinese restaurant, is at 201 E. Harnett St. Mascoutah Community Lanes, at 106 E. George, is listed with pizza, ice cream and a bar, with dine-in and carryout. On a day full of chili, ice cream a few blocks away is good to know about.
If you have any Mascoutah Bucks in a drawer, the festival is a good time to spend them. The Chamber's January 2026 list of businesses that take them includes Camino Real, The Vault, El Sombrero, Skootr's and Mascoutah Community Lanes. That list came out in January, so a quick question at the register before you pay is a good idea.
Coffee is the one thing you won't find on the main festival streets. The City's directory lists no coffee shop or bakery on the downtown blocks. Its bakery listings are on Larkspur Drive, North John Street and Jackson Street, and the Café at Betty Ann Market is at 95 Mascoutah Plaza Dr. If you want coffee before the 10:00 opening, get it on the way in.
One fewer sit-down option this fall
This will be the first Fall Festival since the Mascoutah Steak House closed. Herald Publications reported that it served its last customers on Wednesday, July 1, 2026. At that point no plans for the property had been finalized and no agreements signed, though the hope was that a new business might move in eventually. We haven't seen any follow-up reporting since then.
In practice, the Main Street restaurants listed above will handle festival-day crowds with one fewer sit-down dining room in town. That's useful to know if you plan a late lunch with family around the 3:00 results, when the chili is finished and everyone downtown is looking for a table at the same time.
Five days later, the first Trunk-or-Treat
The festival is the Chamber's event, and it fills Main Street on a Saturday. The second big date in Mascoutah's October is new, run by a different group, and held at a park on a weeknight.
The City's Parks & Recreation Department announced its first annual Trunk-or-Treat for Thursday, October 22, 2026, from 5:30 to 7 p.m. at Scheve Park, 900 Park Dr. It's free and no admission is required. The City promises decorated vehicles, costumes, candy and what it calls "plenty of spooky surprises." The City posted the announcement on October 2.
"Mark your calendars and join us for our FIRST EVER Trunk or Treat!"
Families who want to decorate a trunk instead of trick-or-treating at one have to sign up through the City's online form by Tuesday, October 20. That's three days after the festival. Anyone who wants to reuse festival-weekend energy, or leftover hay bales, has a short window to register.
Because this is a first-year event, there's no past turnout to go on and no traditions yet for how people decorate. The 90 minutes start at 5:30, so families coming from work or practice will likely be heading straight to Park Drive.
The rest of the calendar
The library keeps going after the two big dates, all at 3 W Church St.:
- Teen Art: Spooky Art Night, Thursday, October 29, 4 to 6 p.m., free, for grades 6 through 12
- Youth Book Club: The Lost Library, Thursday, November 12, 4 to 5 p.m., free, no booking needed
- Parent Café with Birth to Five Illinois: Region 50, Saturday, November 14, 10 a.m. to noon, registration required
From the Saturday festival through the Thursday Trunk-or-Treat to Spooky Art Night the following Thursday, Mascoutah's October fits inside about two weeks. The Chamber covers Main Street, the City covers Scheve Park, and the library has events at both ends.
If you have family or friends moving to Mascoutah, maybe on a PCS to Scott AFB, October 17 is a good day for their first look at downtown, and we're glad to help them plan the visit. Delores W Doussard and the Dream Team can also talk through how Mascoutah's blocks compare to the rest of the Metro-East. Schedule a Free Consultation whenever the timing works.
