Horse Eating Hat

Fall Fairs in YDH

They are said to be the oldest festivals and have been celebrated across the world for eons! Harvest Festivals are an annual celebration that give thanks for providing a bounty of crops.

The word harvest is derived from hærf-est, an Old English word that referred to the season of autumn, between August and November. Many fall festivals began as a way for farmers to showcase their goods and sell them. However, over time this was unnecessary and there was a shift into a fun family-friendly event that still celebrates agriculture at its core.

Orono Fall Fair
Ducks at Fall Fair

For as long as Harvest Festivals have been celebrated, there’s always a common theme beyond the main harvest. That theme is one of feasting and merriment!

So, if you’re looking for fun things to do in the fall, then add one of the many Harvest Festivals taking place across York Durham Headwaters to your fall bucket list!

Erin Fall Fair

Horse Eating Hat at the Erin Fair in Headwaters

One of the best fall fairs in the Headwaters Region is in the charming small town of Erin! Every year since 1850, the Erin Fall Fair continues to excite locals and visitors alike.

The fair takes place every Thanksgiving weekend at the Erin Fairgrounds, just north of downtown. For over 170 years the fair celebrates agriculture, family, and fall with a tractor load full of activities and events.

Many call the Erin’s Fall Fair a miniature CNE and Royal Winter Fair with its large midway, livestock exhibits, and horse shows. It is filled with attractions and rides that the kids will love! There are also a ton of animals on exhibit like horses, bunnies, and various livestock. Plus, every year they host a pet show and pumpkin carving contest!

To get your adrenaline pumping the fair puts on fun festivities like tractor pulls and demolition derbies! Check out the vintage tractors too, all of which are over 55 years old.

Visitors can browse the various vendors selling everything from homemade items to local products like honey, fresh vegetables, and preserves.

When: October 6th – 9th 2023

Where: Erin Fairgrounds – 184 Main St, Erin, ON N0B 1T0

Orono Fair 

Central Fair Orono

Since 1852, families have come together to recognize agricultural excellence and honor the harvest at the Orono Fair! As one of the oldest running fairs in the Durham Region, the Fair draws crowds from all around every year on the weekend after Labour Day.

The Orono Fair is one of Durham Region’s largest events with a line up that starts Thursday night. It kicks off with a Demo Cross and follows with an incredible concert Friday night. This year’s headliner is the James Barker Band!

Throughout the weekend the Orono Fair entertains visitors with a wide array of events, exhibits, and activities. It’s home to one of the area’s largest midways! In addition, like many other fall festivals there are tractor pulls and competitions for an assortment of things like livestock, paintings, woodworking, culinary creations, and more! Speaking of food, you’ll want to go on an empty stomach! You’ll find all the best fair foods to fuel your day!

The Orono Fair is a great place to learn more about farming and see where your food and goods come from, as well as the people behind it all!

When: September 7th – 10th 2023

Where: Orono Fairgrounds – 2 Princess St, Orono, ON L0B 1M0

Bolton Fall Fair

Bolton Fall Fair

Another festival in the Headwaters Region is the Bolton Fall Fair! Taking place on the last weekend of September at the Albion Bolton Fairgrounds, the fair is a tradition dating back over 160 years!

The Bolton Fall Fair runs Thursday through Sunday. Families will want to jump in the car and be there for opening night as it’s only a toonie for the midway rides! However, there’s fun to be had all weekend long with truck and tractor pulls as well as motorcycle and dog shows.

Children will get a thrill at the petting zoo! Plus, if you’re looking for a giggle check out the Cow Plop Bingo! Don’t worry, there’s plenty of fun for adults too! The Bolton Fall Fair hosts a Craft Beer & Cider Festival that features local brewers.

Visitors also get a peek into some interesting farming processes with sheep shearing demonstrations and milking competitions.

When: September 21st – 24th 2023

Where: Albion Bolton Fairgrounds – 150 Queen St S, Bolton, ON L7E 1B3

Beaverton Fall Fair

Beaverton Fair

On the east side of Lake Simcoe there’s another picturesque town hosting a harvest festival. At the Beaverton-Thorah Community Centre Arena visitors can join an over 165-year tradition, the Beaverton Fall Fair.

This Durham Region festival takes place annually in the middle of September. The community comes out to cheer on local farmers and artisans as well as all things autumn! It all starts with a parade through downtown leading into the fairgrounds.

There’s so much going on you’ll want to make sure you’ve got your comfortable shoes on! Shows include a talent contest, various horse demonstrations, a car show, and even a wrestling match! The fair showcases an array of competitions too, which cover food, photography, art, and maple syrup.

While many fall fairs put on demolition derbies, the Beaverton Fall Fair ups the game with a derby as well as a freestyle Motocross stunt show!

Along all the shows there’s also a midway and farmers’ market. Plus, you can quench your thirst, on the second floor of the Curling Club at the Beer Garden. But don’t forget to miss the concert downstairs on Friday night!

When: September 15th – 16th 2023

Where: Beaverton-Thorah Community Centre Arena – 176 Main St, Beaverton, ON L0K 1A0

Markham Fair

Markham Fair

Established in 1844, the Markham Fair is one of the oldest country fairs in Canada! This four-day event runs the weekend before Thanksgiving and is a must!!!

With a perfect location in York Region, just north of Toronto, the Markham Fair is one of the best festivals in Ontario! Set on over 100 acres of former farm land, the Markham Fairgrounds is full of fun things to do for kids and adults!

On top of the traditional events like a demolition derby, tractor pull, and livestock demonstrations, the Markham Fair packs in so much more! There’s a giant midway, freestyle motocross, and cooking shows!

Children will love the kid’s zone, entertainers, playground, and circus. Adults are not forgotten! There are wine and beer tents. Plus, visitors will find a jammed packed schedule with events and shows taking place throughout the day in the various buildings.

If all that wasn’t enough, the Markham Fair goes out with a bang every night with fireworks displays at dusk!

When: September 28th – October 1st 2023

Where: Markham Fairgrounds – 10801 McCowan Rd, Markham, ON L3P 3J3

Woodbridge Fall Fair

Prizes at Fall Fair

Woodbridge brings the country to the city with their Fall Fair! Taking place every Thanksgiving weekend, the fair is celebrating 175 years in 2022! The Woodbridge Fall Fair is another York Region fall festival that should not be missed!

There’s something for everyone at the Fair! Visitors will find a midway with rides as well as live music. The wee ones will enjoy the petting zoo, pony rides, and corn maze! Plus, there’s a car show, giant pumpkin contest, and pioneer demonstrations.

Be prepared to delight your sweet tooth with all the fabulous fair foods like tasty pastries. Or if you’ve got the appetite, try your luck at one of the food eating contests!


One of the fun events at the Woodbridge Fall Fair is the Farmer Olympics! Teams of four can participate in a variety of activities to test their skills and strength, like moving a hay bale, gathering eggs, and more. The team that does it the fastest wins!

When: October 7th – 9th 2023

Where: Woodbridge Fair Grounds – 100 Porter Ave, Woodbridge, ON L4L 2A2

More Fall Fairs

Uxbridge Fall Fair

When: September 8th -10th 2023

Where: 180 Main St. S, Elgin Park, Uxbridge, ON

Sunderland Fall Fair

When: September 12th – 13th

Where: 20 Park Street, Sunderland, Ontario L0C 1H0

Grand Valley Fair

When: September 22nd –  24th

Where: 60 Main St N, Grand Valley, ON L9W 5S7

By Stephanie Mayo from The World As I See It

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