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Sep 27, 2019

7 min. read

If you’re in search of some family fun this autumn, look no further than Ontario! You’ll have your choice of fall festivals and events around the province, including some of the oldest fall fairs, within a few hours’ drive of Toronto.

A Canadian Tradition.

Fall fairs are an old hat around here and many date back to the 1800s. Marking the time of the harvest in agricultural communities, fall fairs were transplanted to Canada by the earliest British settlers and have become a mainstay in the province and across the country. These events take place over a few days and usually involve agricultural competitions, home crafts, demolition derbies or tractor pulls, live music and performances and midways. And let’s not forget the traditions of Oktoberfest and Halloween!

Where will you go this fall? Here are just a few of the fun options from which to choose, in order of date.

Bobcaygeon Fall Fair.

September 26-28, 2019 Bobcaygeon Fairgrounds, 47 Mansfield Street, Bobcaygeon

The Bobcaygeon Fall Fair takes place the same weekend as Milton’s Fair, and is now in its 161st year, though (according to the website) its origins date back to 1792 when Canada’s first Lieutenant Governor, John Simcoe, helped to organize the Agricultural Society of Upper Canada. The Bobcaygeon Fall Fair is a fun festival featuring dog and horse shows, a chicken show and other animal shows, a barn dance and parade, a talent show, a truck and tractor pull, a demolition derby, and homecraft and agricultural exhibits. Check it out! After all, Bobcaygeon is where one might see the constellations reveal themselves one star at a time.

A red truck with a canadian flag on it driving down a dirt track.

Milton Fall Fair.

September 27- 29, 2019

Milton Fair Grounds, 136 Robert St, Milton

The Milton Fall Fair began in 1853 and is now in its 166th year. It takes place in late September, and has been in exactly the same spot for 165 of those 166 years. The fair boasts “perfectly groomed calves being proudly paraded by 4-H Club members” and “Instagram worthy crafts and baked goods.” Events and attractions include the midway, equestrian events, a kids’ pet show, a baby contest, truck and tractor pulls, a demolition derby and live bands. The fun kicks off with Youth Day, a special preview of the agricultural fair for children, and the weekend features kid-friendly events including dog agility shows, the 4-H Club’s rabbit hopping agility course, and a children’s pedal tractor pull.

A group of dogs in a line at a dog show.

Markham Fall Fair.

October 3-6, 2019

10801 McCowan Road, Markham

Closer to home, if home is Toronto, is the Markham Fall Fair, one of Canada biggest and oldest country fairs. It was established in 1844, which makes it 175 years old, and it takes place annually over four days on the weekend before Thanksgiving. The Markham Fall Fair attracts more than 60,000 visitors and approximately 3,000 exhibitors entering more than 10,000 items into competitions. You will also find farm animal displays and a livestock show, a horse pull, demolition derby, tractor pull and midway rides. Oh, and an RCMP Musical Ride, music concerts, an aerial circus show, fireworks and more. Looks like a pretty good time.

A group of men on horses.

Erin Fall Fair.

October 10-14, 2019

Erin Agricultural Society, 184 Main St, Erin

The Erin Fall Fair is in its 169th year, despite a fire that destroyed the main fair building in 1994. It takes place over Thanksgiving Weekend and is hosted by the Erin Agricultural Society, whose mission is to “create awareness and to foster education about agriculture, farming and country life.” At this fair, which calls itself “Ontario’s preview to the Royal Winter Fair” you’ll find a midway, an outdoor entertainment tent, a lumberjack competition and demolition derby, a petting zoo, truck and tractor pulls, livestock shows, homecrafts, a giant pumpkin contest and more.

A man cutting wood with a chainsaw.

Kitchener-Waterloo Oktoberfest.

October 11-19, 2019


The 40-year-old Kitchener-Waterloo Oktoberfest, is held over a week in October. Fun fact: the first Oktoberfest was held to celebrate the wedding of Bavaria’s Crown Prince Ludwig and Therese Von Sachesen-Hildenburghausen in 1810. The local version was established to celebrate the Kitchener-Waterloo’s German Canadian heritage. Oktoberfest features food, drink, fun, Canada’s biggest Thanksgiving Day Parade, a car show, a harvest celebration and more.

A group of men dressed in traditional bavarian costumes dancing.


Selected dates, September 27 – October 27, 2019  Upper Canada Village, 3740 County Road 2, Morrisburg

While not a fall festival, Pumpkinferno at Upper Canada Village promises to be visually spectacular and great for the kids. This award-winning event is held from late September to the end of October and features an exhibit of 7,000 handcrafted pumpkins (!!) all lit up along a kilometer long path in a recreated 1860s village. The pumpkins are actually artificial pumpkins that have been shaped from molds of real pumpkins and then designed and carved by young artists from the Eastern Ontario region. Eat an early dinner at a local restaurant before taking your tour to complete the experience.

Many carved pumpkins are lit up at night.

Image of Monster Truck courtesy of the OTTPA.

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