CHESTER, IL — August 3, 2026 — 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 two major highlights: the “Tailgate Territory” sports streaming zone and a powerful
“Legacy Lawn” military tribute.
The festival officially opens on Thursday, October 15, at 6:00 PM with the 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 can honor a veteran or
active service person by purchasing a customized lawn sign for $20. These signs will be on
display throughout the weekend, and buyers can keep them after the festival conclusion.
Our community has a deep history of service, and the Legacy Lawn allows us to visually
salute that courage across generations. Combined with our brand-new Tailgate Territory
and incredible musical lineup, this year’s festival offers a perfect balance of heartfelt
tribute and high-energy fun for all ages.
The four-day event features a packed schedule of daily and nightly attractions:
- Thursday, Oct 15: Legacy Lawn Dedication (6:00 PM) followed immediately by “That
One Eyed Guy” Popeye-style comedy show.
- Friday, Oct 16: “Tailgate Territory” debuts in the Beer Garden streaming the CHS
football game live. Rock band Stone Blanket takes the main stage in the evening.
- Saturday, Oct 17: 5K Run in the morning, Crafts & Curiosities market, and the
annual Festival Parade at 11:00 AM. Afternoon events feature a Burger Eating
Contest, followed by a headline performance by country artist Ryan Daniel on his
Adrenaline Rush Tour 2026 that evening.
- Sunday, Oct 18: Family Day featuring balloon sculpting, face painting, strolling
magic, and “The Magic of Joshua” Illusion Show. A grand fireworks display closes the
festival on Sunday evening.
Chester’s annual Fall Festival has officially partnered with Swyear Amusements to provide
the carnival rides and midway attractions for the upcoming four-day event at Cole
Memorial Park from October 15–18, 2026. This year’s festival, which proudly celebrates
America, will feature armband sessions daily, including a special “After School” promotion
on Friday afternoon.
Swyear Amusements will operate the midway every day of the festival, offering unlimited-
ride armbands during designated time slots. Families looking for maximum value can take
advantage of the special After School session on Friday, October 16, from 12:00 PM to 4:00
The complete, detailed schedule of armband session times will be released to the
public in the coming weeks.
We are thrilled to bring Swyear Amusements on board to deliver a top-tier carnival
experience for our families, the daily armband sessions and the Friday early-bird special
make the festival more affordable and exciting for everyone.”
Carnival rides, games, a beverage stand, a mechanical bull, and poker stands will operate
every day of the festival. Organizers are actively seeking sponsors and are currently
registering parade entries.