What’s Happening in Chatham-Kent: May 23–25, 2025

angelwagenaar
May 23
3 min read

Discover what's happening in Chatham-Kent this weekend. From classic cars and live music to baseball games and drive-in movies, there’s something for everyone to enjoy between May 23–25. Here's your complete guide to the top events happening across the region, including RetroFest™ 2025 and much more.

RetroFest™ 2025: Chatham’s Favourite Summer Kickoff

Location: Downtown Chatham & Tecumseh Park

Admission: $2.00 admission to park, children 12 and under free

What’s Happening in Chatham-Kent” featuring classic cars, a flaming baseball, a horse and jockey, and a microphone silhouette on a yellow background. Highlights local events in Chatham-Kent.

RetroFest™ returns this year with even more excitement. Expect three days packed with vintage vibes, live entertainment, food trucks, family fun, and local vendors—all in the heart of Chatham, Ontario. Whether you're a local or visiting for the weekend, RetroFest™ is one of the top events in Chatham-Kent.

RetroFest™ Schedule

Friday, May 23

3:30 – 11:00 PM – Vendors & Food Trucks at Tecumseh Park
3:30 - 4:30 PM – Chatham Christian School Band
5:30 - 7:00 PM – Southwind Buoys
7:30 - 9:00 PM – Blutonium
9:30 - 11:00 PM – Face4Radio
4:00–8:00 PM – Parking Lot Party featuring Courtney Wells LIVE

Saturday, May 24

10:00 AM – 11:00 PM – Tecumseh Park Activities
10:00 AM – 12:00 PM – Soap Box Derby
12:00 PM - 1:30 PM - Ms. RetroFest ™ Pageant
1:30 PM – Rock Accordingly
3:00 PM - Classic Car Show Awards
4:00 PM – Jen Knight Trio
5:30 PM – British Beat 66
7:30 PM – Painkiller Jane
9:10PM - Fireworks in the Park by RM Auto Restoration
9:30 PM – Carson Janik
11:00 PM – After Party at The Garden with DJ N8

Live Music in Chatham-Kent: Weekend Lineup

Chatham-Kent’s live music scene is in full swing this weekend. Enjoy local bands, acoustic sets, and tribute shows at your favourite breweries and venues.

Crowd enjoying a vibrant outdoor music festival in Chatham-Kent, with colorful smoke effects and a large concert stage lit up during a live performance.

Friday, May 23

Justin Maki at The Garden – 7:00–10:00 PM
Carly Thomas at Glasstown Brewery – 7:00 PM
Dreamer (Supertramp Tribute) at Capitol Theatre – 8:00 PM

Saturday, May 24

Just Us Trio at The Garden – 5:00–8:00 PM
Trifeckta at Sons of Kent – 7:00–10:00 PM
Garth & Shania Tribute at Capitol Theatre – 8:00 PM
Epic Eagles at Kiwanis Theatre – 7:30 PM
Kenny and Joel Acoustic Show at Level Up Arcade – 8:00 PM

Sunday, May 25

Brian Gardiner at Glasstown Brewery – 4:00 PM

Chatham-Kent Sports and Racing Events

Get your sports fix this weekend with local baseball, speedway races, and wrestling.

CK Barnstormers Home Games

Saturday, May 24 – vs. Brantford Red Sox – 7:05 PM
Sunday, May 25 – vs. Guelph Royals – 2:05 PM

More Weekend Action

Buxton Speedway – Saturday, May 24 – 6:30 PM
Dresden Raceway Opening Day – Sunday, May 25 – 1:00 PM
Hammerlock Wrestling at W.I.S.H Centre – Sunday, May 25 – 2:00 PM

Family-Friendly Activities and Outdoor Events

Looking for low-key fun? Bring the family and enjoy Chatham-Kent’s outdoor entertainment.

The Boonies Drive-In Theatre (May 23–25)

Double Feature: Lilo & Stitch + Thunderbolts
Showtime: 9:30 PM nightly

Friday Night Social

Wine Club Social at Willow Ridge Golf & Country Club – 7:00 PM

What’s happening in Chatham-Kent This Weekend

Whether you're enjoying family time or exploring with friends, Chatham-Kent is packed with memorable experiences. From the nostalgic charm of RetroFest™ to exciting sports and live performances, this weekend has something for every interest.