Countdown is on for this week’s 2026 Caledon Fair

June 18, 2026 · 0 Comments

By Riley Murphy

Local Journalism Initiative Reporter

Demolition Derbies, Truck and Tractor Pulls, and Classic Car Shows, Oh My! The 2026 Caledon Fair is back in town.

Starting on June 19, the Caledon Agricultural Society (CAS) is bringing back their annual fair.

The fair, which has been running in Caledon Village since 1860, brings together both agricultural awareness activities and fun festivities to offer something for everyone at the yearly event.

The fair kicks off Friday evening, at 5 p.m., with the Ontario Truck and Tractor Pull Association’s Truck and Tractor Pull, with vintage classes taking off first.

Saturday, June 20, will bring the All British Classic Car Show, the Fair Ambassador Competition, the official opening of the Fair at 12 noon, a baked goods auction for Bethell Hospice and MS Society, live music by the Muir Band, and the Demolition Derby kicking off at 5:30 p.m.

The last day of the Fair on Sunday, June 21, will feature the Welsh Pony Show and SportPony Starsearch, the Cheval Canadien Horse Show, the Beef and Dairy Show, the Belgian Horse Display, and much more.

Running all weekend will be returning favourites such as pony rides and the petting zoo, the inflatable play park, the Agricultural Awareness and Exhibits Hall, the Bavarian Garden, and the Knox Church Food Booth.

Ed Taccone, President of the Caledon Agricultural Society, adds that this year, to raise money for their brand-new building, they are holding a raffle for the grand prize of a 2025 Kubota RTV Off-road vehicle.

Each raffle ticket purchased also goes towards subsequent prizes, drawn throughout the summer and into the winter.

Tickets can be purchased through the CAS Secretary at 416-697-7792.

Brand new to the fair this year, CAS is partnering with the Caledon Lions Club to bring the “Caledon Lions FUNDrive Cart Race” to the event.

On Sunday, the Lions will run their cart race for the first time ever, with a start time of 11 a.m.

Teams of four will race to see who has the fastest time, and prizes will also be awarded for the best theme/costume.

Two carts will participate per heat, with a 50 metre slalom out, and sprint back for completion.

The Lions add that bragging rights will be “for the taking.”

Jeevan Randhawa, Marketing Communications with the Caledon Lions Club, says this year, in partnering with the CAS, they wanted to bring something to the fair that was interactive, something for the community to take part in.

And so, the idea for the cart race was born, “a friendly competition within the community,” says Randhawa.

Randhawa says the entire project was funded and built from scratch by the Lions.

“We wanted an event that was unique and interactive, and where the community can actually be engaged in,” he says, adding that they hope to make it an annual event.

They encourage businesses, community groups, and community members to form teams for the event.

Money raised from the race will go directly back into the community.

Interested participants who are looking to register for the cart race can call 519-278-0678

To view the full schedule for this year’s fair, visit www.caledonfair.ca/events/caledon-fair-2026.