The countdown is nearly over for one of Caledon's oldest traditions. The 2026 Caledon Fair opens in Caledon Village on Friday, June 19, and runs through Sunday, June 21.

The Caledon Agricultural Society (CAS) runs the annual event, which dates back to 1860. According to the Caledon Citizen, the fair combines agricultural awareness activities with festivities aimed at offering something for every visitor.

Weekend schedule packed with pulls, derbies and car shows

The fair kicks off Friday at 5 p.m. with the Ontario Truck and Tractor Pull Association's Truck and Tractor Pull, with vintage classes leading off.

Saturday, June 20, brings the All British Classic Car Show, the Fair Ambassador Competition and the fair's official opening at 12 noon. A baked goods auction will raise money for Bethell Hospice and the MS Society, the Muir Band provides live music, and the Demolition Derby starts at 5:30 p.m.

Sunday's finale features the Welsh Pony Show and SportPony Starsearch, the Cheval Canadien Horse Show, the Beef and Dairy Show, the Belgian Horse Display and more.

Returning weekend-long favourites include pony rides and a petting zoo, the inflatable play park, the Agricultural Awareness and Exhibits Hall, the Bavarian Garden and the Knox Church food booth.

New Lions Club cart race makes its debut Sunday

Brand new this year, CAS has partnered with the Caledon Lions Club for the Caledon Lions FUNDrive Cart Race, which runs for the first time ever on Sunday at 11 a.m.

Teams of four will race for the fastest time, with prizes also awarded for best theme and costume. Two carts will compete per heat, each running a 50-metre slalom out and a sprint back to the finish. The Lions say bragging rights will be "for the taking."

Jeevan Randhawa, marketing communications with the Caledon Lions Club, told the Caledon Citizen the club wanted to bring something interactive to the fair that the community could take part in — "a friendly competition within the community," as he described it.

We wanted an event that was unique and interactive, and where the community can actually be engaged in

Randhawa said the entire project was funded and built from scratch by the Lions, who hope to make the race an annual event. Businesses, community groups and residents are encouraged to form teams, and money raised from the race will go directly back into the community.

Raffle supports new building

Ed Taccone, president of the Caledon Agricultural Society, said this year's fair also includes a raffle to raise money for a brand-new building. The grand prize is a 2025 Kubota RTV off-road vehicle, and each ticket purchased also enters draws for subsequent prizes running through the summer and into the winter. Raffle tickets can be purchased through the CAS secretary at 416-697-7792.

Teams interested in registering for the cart race can call 519-278-0678. The full fair schedule is available at caledonfair.ca/events/caledon-fair-2026.