12 fall fairs for family-friendly fun

Published: September 26, 2019

ferris wheel at the bobcaygeon fall fair Photo by Fred Thornhill

The leaves are changing, which means it’s time to welcome fall with open arms. Although we always say summer is our favourite season, activities like apple picking and cottage hunting make this time of year a close runner-up. 

One of the best parts about cottage country during the cooler months? It’s a mecca for fall festivals. From demolition derbies to pumpkin seed-spitting contests, everyone can find something to love at the fair. 

Here are the can’t-miss events in Ontario this season.

Bobcaygeon Fall Fair
When: September 26-29
What: This is one of those can’t-miss events—after all, it is referred to as the “The Daddy of ‘em all”. Not only will you enjoy the changing leaves and being lakeside, you have an entire line-up of fair favourites. Kick it all off with a parade, go see the animal exhibits, dance up a storm, and then sit back and relax at the Craft Beer Tasting. CL tip: If you’re planning on going to some of the main events, like the Demolition Derby and Truck and Tractor Pull, head over early to secure a seat.

Caledonia Fair
When: September 26-29
What: There are so many reasons to head to this fair—from the Battle of the Butter Tarts to the two-night Demolition Derby, you just might have to go every day! One thing is for sure, every event revolves around building memories and creating community—the theme for this year’s fair. We highly suggest checking out the pet show to check out some of your neighbours real and stuffed furry friends.

Coldwater Fall Fair
When: September 27-29
What: This North Simcoe County fair grows larger every year with partial thanks to the environmental route it takes to promoting the weekend’s events. This year the focus is on trees and sustainable forestry practices, meaning the entire family can learn something about agriculture while enjoying the fall festivities. Head here for the much-loved Nail Driving and Log Sawing competition, as well as the newly added Zucchini Drag Race.

Belleville’s Flavours of Fall
When: September 29
What: Head to downtown Bellville and celebrate the harvest season. Start the day by indulging in the deliciousness of fall at the farmers’ market with a cup of hot apple cider. Then head over to the arts and crafts area for an afternoon of pumpkin carving, corn husk doll making, and face painting. There will also be free horse-drawn wagon rides and pony rides for anyone who loves animals.

Markham Fair demolition derby
Photo courtesy of Markham Fair

Markham Fair
When: October 3-6
What: If you’re in the GTA this fall, you have to go to one of Canada’s oldest and largest fall fairs. From the midway to the farm animals, there’s all your classic fair festivities, and then some. Every day has a headlining event — Friday is the Truck and Tractor Pull, the Heavy Horse Show and Demolition Derby are on Saturday, and Sunday features Monster Truck Madness. If the big events aren’t for you, take a walk through the homecraft building, where you’ll enjoy the never-ending displays of baked goods, homemade quilts, and photography.

Port Elgin Pumpkinfest
When: October 5-6
What: From baking to decorating, you know we’re all about squash season. This pumpkin-palooza in Saugeen Shores is a must-see for anyone who feels the same. You’ll see some of the biggest pumpkins in the province here when everyone carts them in for the annual Giant Pumpkin Drop. Enjoy more of what fall as to offer at the Saturday Harvest Supper, and join in on some fun and games, like the Celebrity Seed-Spitting contest and the Pumpkinfest Pursuit 5K.

Norfolk County Fair and Horse Show
When: October 8-14
What: One of the largest fairs in Ontario is ready for you and the family with a line-up of kid-friendly events and some for just the adults too. It starts with a Harvest Dinner, and includes a karaoke competition, a scavenger hunt, an educational agriculture program, six nights of motorsports events, and a beer and wine tent with live entertainment.

elmvale fall fair midway
Photo courtesy of Elmvale Fall Fair

Elmvale Fall Fair
When: October 10-12
What: While the turkey is in the oven, head over to this jam-packed festival just north of Barrie, in the Horseshoe Valley area. Along with a midway full of rides and candy apples, you can look at over 100 different categories of contest entries, like baked goods and nature photography. We suggest planning your visit around some of the fair’s major events—the Friday evening tractor pull always draws a crowd! And on the way home, make sure to drive by some of the residential ‘Roadside Decorating Contest’ winners.

Fall Fair lawn mower races
Photo courtesy of Norwood Fall Fair

Norwood Fall Fair
When: October 12-14
What: Take some time this Thanksgiving weekend to get out of the kitchen and over to this charming town fair. You’ll spend an entire afternoon taking in all of the craft and homegoods exhibits, and enjoy the focus on agriculture and livestock. One of the biggest draws is the Nascar-style Lawn Mower Race, which we highly suggest planning your visit around.

Apple Festival and Craft Sale – Bowmanville
When: October 19
What: You’ve seen the leaves changing colours and the apples growing bigger on trees, so now’s the time to enjoy it all. Downtown Bowmanville will transform into an apple-pickers paradise for the 30th anniversary of this local growers showcase. Get ready for apple everything—from cider to crisps to the famous fresh fritters, you’ll definitely need to wear your stretchy pants here. Walk off the treats at the artisan market and take in the talent of the local community.

Pumpkin tiger sculpture
Photo courtesy of Pumpkins After Dark

Milton’s Pumpkins After Dark
When: September 26-November 2
What: To (pumpkin) spice things up a bit, we’re adding this festival to our calendar even though it’s not your typical fall fair. This outdoor art exhibit in Country Heritage Park features over 5,000 hand-carved pumpkins and 100 squash sculptures, all with special lighting, sound effects, and a spooky musical score. You won’t believe some of the jack-o-lantern talent out there–get your tickets now before the event sells out!

Horse show at the Royal Agricultural Winter Fair
Photo courtesy of The Royal Agricultural Winter Fair

The Royal Agricultural Winter Fair
When: November 1-10
What: This is one of the biggest celebrations of fall, putting the spotlight on our love of local everything. There’s a competition for just about everything here: from food (you’ll find us at the butter tart booth) and livestock, to sculptures, and square dancing, you’ll see the best of what Ontario offers. But you don’t have to compete to enjoy the fair. Take in one of the horse shows, enjoy some live musical entertainment, or stop by the Cottage Life booth. See you there!

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