After two years of cancellations or reduced offerings, fall fairs are finally back up and running. It’s more than welcome, as these much-loved events help mark the season by celebrating all things fall, from the harvest to hayrides and pumpkin carving. Add these fall fairs in cottage country to your calendar, and consider making the rounds—there are a few towns celebrating big milestones this year.
Bobcaygeon Fall Fair: September 29–October 1
Billed as “The Daddy of ‘Em All” when it comes to fall fairs, the Bobcaygeon fair is jam-packed with events over three days and definitely lives up to the name. Fans of a classic demolition derby won’t be disappointed by the one put on here. There’s also a typical roster of events like the truck & tractor pull, a parade, and a Saturday night dance with live entertainment. Weekend passes go for $25 per person, and while parking is limited, a free shuttle runs from nearby Tommy Anderson Park.
Caledonia Fair: September 29, 30 and October 1, 2
With the slogan, “The Country Fair of Your Memories,” Caledonia has fun, nostalgic activities for people of all ages—like Midway rides and a demolition derby, plus a slate of local vendors selling food and handmade goods. There’s also a designated Kids’ Zone and a ‘passport program’ that provides a scavenger hunt to complete across the fairgrounds. This year marks the fair’s 150th anniversary, so there’s bound to be an extra celebratory atmosphere.
Port Elgin PumpkinFest: October 1-2
A whole festival dedicated to the most famous crop of the season? Yes, please. The central event for this festival is the pumpkin weigh-in, where hopeful growers bring in the largest pumpkin they can harvest for the chance to win a prize—you really have to see them to believe it. Beyond that, there’s a popular classic car show and tons of delicious local food vendors—many incorporating pumpkin—to keep you satisfied.
Norfolk County Fair: October 4-7
The Norfolk fair takes place over a whole week and is packed with events, including concerts by Walk Off the Earth and the Hunter Brothers. It’s a popular event and offers advance tickets, so look into it if you want to secure your spot. There’s a large market showcasing local goods, plus different events each day, from shows by local choirs to axe-throwing competitions and other Motorsport games.
Elmvale Fall Fair: October 7-8
A perfect tie-in to Thanksgiving festivities, this fall fair is hosted by the Flos Agricultural Society and is celebrating 160 years. With midway rides, farm animal displays, and parades, this is a great family-friendly activity for the weekend if you’re in the area. There’s a kids’ tractor pull in addition to the main one, plus locally curated photography and floral exhibits.
Norwood Fair: October 8-10
Also taking place over the Thanksgiving weekend, the Norwood Fair is back with the theme “Autumn Treasures” after a couple of years of closures. With an antique car show, craft exhibits, and the harvest on display from local farms, there’s plenty of reason to stop by this picturesque town. Norwood also has an impressive slate of horse-related events, like Equestrian and Western shows, relay competitions, and barrel races.
Milton Pumpkins After Dark: September 23-October 30
It’s never too early to get into spooky Halloween vibes, and there’s no better way than to see this pumpkin-themed light installation—a great spot for a photo-op. There’s more to it than the tunnel walkthrough, with live pumpkin carving and vendors selling fall-centric treats. This event takes place in cities across Canada and has become pretty popular, so be sure to book your spot in advance as it’s likely to get busier as the month goes on.
The Royal Winter Fair: November 4-13
This famous, renowned fair is back in early November and is bound to be well-attended given closures over the past two years. The Royal Winter Fair centres around horse shows and horse-related events, which are certainly a spectacle and worth seeing. But there are also many local artisans, craft shows, and other exhibits on display. It’s easy to make an evening out of your visit, too, with great restaurants and a wide range of choices for dedicated foodies.