Chester’s Annual Fall Festival returns to Cole Memorial Park from October 15–18, 2026,
featuring a weekend of community celebration, live music, and family entertainment. This
year’s festival theme proudly celebrates America and debuts some major highlights: the
“Tailgate Territory” sports streaming zone and a powerful “Legacy Lawn” military tribute as
well as a Flag Ceremony performed by the Sparta Army National Guard, that “One Eyed
Guy”, and much more.
Thursday, October 15, at 5:30 PM there will be formal dedication of the Legacy Lawn inside
Cole Memorial Park. The lawn stands as a living tribute to 250 years of military service,
honoring local community individuals who have defended, and continue to defend, the
nation’s freedom. Community members honored a veteran or active service person with a
customized lawn sign in their honor. Don Berry will give the dedication for this special lawn.
These signs will be on display throughout the weekend.
Following the dedication there will be a Flag Ceremony at the entrance of the Fairgrounds
at 6 pm. The Sparta Army National Guard will lower the flag for the evening in proper
ceremony.
Our community has a deep history of service, and the Legacy Lawn allows us to visually
salute that courage across generations, combined with the Flag Ceremony we will start
this year’s festival with a perfect balance of heartfelt tribute and high-energy fun for all
ages.
Join us for a Free Halloween Costume Giveaway at the Fall Festival! Get ready for spooky
season without breaking the bank! We are thrilled to announce a Free Halloween Costume
Giveaway taking place during our upcoming Fall Festival on Thursday, October 15th, from
5:00 PM to 8:00 PM.
We will have a fantastic selection of new costumes available for toddlers to teens.
Everything is completely free and distributed on a first-come, first-served basis while
supplies last. One per child. Come for the festival activities and leave ready for trick-or-
treating! This event is made possible by the generous donation of Chester Wal-Mart.
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This event is open to everyone in the community. Bring your family, enjoy the crisp fall air,
and pick out a great costume! For more information or to inquire about dropping off a
costume donation ahead of time, please contact [Insert Contact Info].
Swyear Amusements evening session, 5-9 pm, will offer an armband for $30 each. You will
want to come on out and see the new attraction!
Penny, the Mechanical Bull, will be waiting for you this weekend. Can you tame the beast?
Grab the horns and hold on tight! Penny is being brought to us by The Bullpen Sports Bar.
Penny will be there every day of the festival.
Food and Drink Stands open at 4 pm and the Poker Stand opens at 6 pm.
This year we bring you, “That One Eyed Guy”. Join us on October 15th at 6:00 PM for a night
of laughs, a spinach-eating contest, and strongman grip challenges that will kick off the
four-day fall festival! Think you’ve got what it takes to stay strong to the finish and win?
Enjoy the ultimate rivalry, Popeye vs. Brutus! They face off in a brawl sure to bring you
laughs! This is a FREE show! There has been a rumor that you might get a glimpse of Swee
’Pea at the festival!
Friday the festivities will begin at 2 pm with the After School Special. Purchase an armband
for $15 that is good from 2-4 pm. Students can enjoy the amusement rides for 2 hours
before the official start of the festival. Evening session (5-10 pm) armbands are $40 each.
Come out to the Beer Garden at Chester Fall Festival 2026! For the debut of “Tailgate
Territory”! Thanks to our friends at Rent One, we will have the regional and national games
broadcasting live on giant screens right in the heart of the action.
ON FRIDAY, Chester YELLOWJACKETS will play at Nashville, but you don’t have to miss a
single second of the action. We will be streaming the CHS football game live, giving you the
perfect spot to cheer on the Yellow Jackets.
Friday evening Stone Blanket will take the main stage from 8-11 pm. Stone Blanket is a high-
energy rock cover band. They specialize in a crowd-pleasing mix of rock styles spanning
from the 1970s to today.
The four-member lineup is known for seamlessly shifting between several sub-genres:
classic rock, southern rock, alternative rock, pop rock and hard rock.
Saturday is a full day of fun. Starting off with the Chester Running Club’s 5K Race at 9 am.
Don’t head home after the race, get ready for the Fall Festival Parade at 11 am. The parade
will make its way from Chester High School to the Courthouse. Keep an eye out for a
special appearance from our own “One Eyed Guy”.
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The Crafts & Curiosities Market will be located at the entrance to the Fairgrounds, 10 am-4
pm. Some of the items the vendors will be offering include candy tins, scrunchies, cell
phone cases, crocheted items, shirts, baked goods, leather goods, Arbonne, wallets, flags,
knives, jewelry, jewelry boxes soap, goat milk soap, woodworking, décor crafts, Hot
Wheels, Nascar items, baseball cards, and much more.
Windy Bill’s Hamburger Eating Contest registration begins at 1 pm and the contest starts at
2 pm. How many burgers can you eat in 10 minutes? Let’s find out! Free to enter and
hilarious to watch!
The Ultimate Saturday Lineup at Cole Park! Saturday, October 17th is officially a jam-
packed day of events at the Chester Fall Festival 2026, and we’ve made sure you won’t
have to choose between family festival fun and your favorite college football matchups!
Whether you are wearing Mizzou Black & Gold, SIU Maroon, or SEMO Red, we have you
covered.
This year we bring a new event, the Chester Cruise-In located at the back of the
fairgrounds. No entry fee.
Chester Cruise-In is a relaxed social gathering where car enthusiasts meet to showcase
their vehicles and socialize with other owners, while the public gets to enjoy the beauty of
the vehicles.
Swyear Amusements will offer armbands for $30 each at each of the Saturday sessions. (1-
5 pm and 6-10 pm).
Ryan Daniel “Adrenaline Rush” Country-Rock Tour comes to Chester Fall Festival. Bring
your chair, bring your friends and get ready for the “rush”.
Ryan Daniel is a highly decorated independent country music sensation and a 10-year U.S.
Air Force veteran. Known for his powerful vocals and an electrifying, high-energy stage
presence heavily inspired by Garth Brooks, he is bringing his 2026 “Adrenaline Rush” Tour to
headline the City of Chester Fall Festival 2026 at Cole Memorial Park Fairgrounds on
Saturday, October 17th at 8:00 PM.
Before striking out as a solo artist, Ryan served over a decade in the Air Force as an AMMO
troop. During his service, he toured 20 countries entertaining over 250,000 troops as a
member of the elite military showcase “Tops in Blue”. He has been honored with the U.S. Air
Force Veteran In Blue Award.
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He blends a gritty, authentic country-rock sound with stadium-sized energy. His live
performances are designed to get crowds moving, making his current tour title—Adrenaline
Rush—the perfect descriptor for his sets.
Ryan is an Indie Music Hall of Fame inductee with over 20 Indie Music Awards and multiple
Spotify platinum certifications for millions of streams. Some of his biggest hits include
“CAMO”, “Already Gone”, and the fan-favorite anthem “Backroads and Bonfires”.
Over his decade-long career, he has toured alongside country and rock superstars like
Trace Adkins, Rodney Atkins, Gabby Barrett, and 3 Doors Down.
Sunday brings the Strolling Magic of Joshua Heck and at 4 pm The Magic of Joshua Magic &
Illusion Show. This is a FREE event and will be on the main stage.
The high-octane excitement of RC racing is coming to our annual Fall Festival! We are
thrilled to announce that Me-2-You Game Truck will be onsite, bringing their premium,
action-packed remote-controlled car track to Chester. Festivalgoers of all ages will have
the unique opportunity to step into the driver’s seat, grab the controller, and test their skills
navigating precision RC vehicles through a thrilling, custom-built course. This hands-on,
high-energy attraction joins a fantastic lineup of community activities, ensuring a
memorable day of friendly competition and family fun. Tickets will be $5 and are available
at the Central Stand.
From 1-6 pm fairgoers can step into a world of natural wonder at our festival with the
enchanting Butterfly Exhibit from Impact Entertainment. This unique, interactive
experience brings a beautiful habitat right to our community, allowing guests of all ages to
get up close and personal with dozens of magnificent butterflies. Visitors can stroll through
a beautifully landscaped enclosure, marvel at the vibrant colors, and even use special
nectar feeding sticks to invite these gentle creatures to land right on their hands. It is an
educational, highly photogenic, and unforgettable attraction that is sure to be a favorite
highlight for families looking to add a little magic to their festival day. Armbands are $5
each, are good for the entire 5 hours and will be available at the Central Stand.
Kids can enjoy FREE balloon Sculpting and Face Painting Sunday, 1-4 pm courtesy of the
City of Chester.
Swyear Amusements will offer armbands for $25 at the first session on Sunday, 1-5 pm and
$30 at the second session, 6-10 pm.
Chester’s premier NFL game-day hub! Bring your family and meet your friends at the
festival for fun and your favorite gridiron rivalries!
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Whether you are rocking the local colors of the Chiefs, the Bears, or supporting any other
team across the league, we have you covered. Football fans can immerse themselves in
the ultimate game-day atmosphere, festival eats, and giant screens. Parents can kick back,
track their fantasy lineups, and catch every crucial down while the kids enjoy boundless
festival activities, games, and the mechanical bull rides right nearby.
Stick around after the final whistles blow and the post-game analysis wraps up to celebrate
the day’s biggest attraction…FIREWORKS!
You don’t have to miss a single touchdown to enjoy the best festival weekend of the year.
Grab your crew, throw on your favorite jersey, and join us in Tailgate Territory for the
ultimate family-friendly tailgate party. Chester’s premier game-day hub for the weekend!
Fall Festival shirts are on sale now. Adult sizes are $20 and kid sizes are $15. Order yours
now!
Don’t forget to get your 50/50 Tickets. $5 each or 5 for $20. Available now at Chester City
Hall and at the Fairgrounds during the Festival.
For more information visit our website at www.chesterill.com or call 618.826.1430.
All events are subject to change.
Thank you for your time and consideration.
Patti Carter,
City of Chester Recreation Director