Family-Friendly Things To Do in September in Toronto

Happy back-to-school month! You and your family made it through another hot, sticky summer and now it’s time to celebrate a return to routines (and cooler weather) with one of September’s many fun events. Here are 14 local activities that we think your family will love.

Taste of the Kingsway

Can your family not get enough of food festivals? Or maybe they’re huge fans of midway rides and games? Either way, Taste of the Kingsway is for them. This annual event features three stages of live entertainment, a dog show that your family pup can compete in, tons of rides and games and, oh yeah, dozens of delicious food vendors. Entry is free but make sure to bring plenty of cash for all those tempting food samples.

When: September 6-8
Where: Bloor St W between Prince Edward Dr and Montgomery Dr


Back for its third year, this community-oriented festival is all about celebrating life in East York. Locally based shops, artisans and restaurants will be on hand selling their specialties. There will also be a kids’ zone that will entertain your little ones while you shop and check out the swap zone or take part in one of the many other on-site activities, such as tarot card readings.

When: September 7
Where: Danforth Ave & Woodbine Ave

Cabbagetown Festival 

It might be September but that doesn’t mean that street-festival season is quite done yet. One of Toronto’s oldest neighbourhoods is also home to one of the most family-friendly fests out there. Besides offering delicious food from around the world and talented craftspeople, this event is packed with fun activities for the kids. Past years have included bouncy castles, drag queen storytime and even a pirate ship.

When: September 7 & 8
Where: Parliament St from Wellesley to Gerrard, and on Carlton St from Ontario to Parliament

Museum of the Moon

Have a wannabe astronaut in your household? Then head over to the Bentway, located under the Gardiner Expressway, for Museum of the Moon, a seven-metre wide art installation that will let the kids and you get up close and personal with the moon. A variety of activities will take place during the week including astronomy talks and a special wrap-up party that will feature amateur crowd-based singing group Choir! Choir! Choir! All events are free and take place after dusk but before 11 pm.

When: September 10-15
Where: The Bentway, just east of 250 Fort York Blvd

Cirque de Soleil Alegria, In a New Light

Have a night to remember with a trip out to Cirque de Soleil’s updated version of its visual masterpiece, Alegria. Packed with clowns, costumes and of course jaw-dropping acrobats and choreography, this show is best suited for kids who are comfortable sitting in their seats for at least 60 minutes. Regular ticket prices start at around $70 but discounts are available, including a family pack that can save you up to 20% off.

When: September 12-December 1
Where: Ontario Place, Lakeshore Blvd W

Great Canadian Shore Cleanups 

These are tough times for Mother Nature, so give her a helping hand by cleaning up our city’s parks and beaches. On Friday, September 13, join the staff of the Toronto Zoo as they tidy up Rouge Park. Then on Sunday, September 15, the project moves to Sunnyside Park/Beach, for a cleanup sponsored by Ripley’s Aquarium. Garbage bags and gloves will be provided but you’re recommended to bring your own gloves if you have a latex allergy. There’s no fee to participate but you are encouraged to register in advance.

When: September 13 & 15
Where: Rouge Park (Zoo Rd) & Sunnyside Beach (Parkside Dr and Lake Ontario)

Roncesvalles Polish Festival

North America’s largest celebration of Polish culture returns with perogy-making lessons, a classic car show and a Saturday night polka party. The family zone is also back, with rides, games and kid-friendly entertainment including colourful buskers. Roncesvalles’ many awesome shops (which include Hey Kiddo! and Early Bird and Worm) will also be offering some great deals.

When: September 14-15
Where: Roncesvalles Ave between Dundas W St and Queen St

Open Streets TO

2019’s second and final Open Streets event will once again see long sections of Bloor and Yonge streets shut down to vehicle traffic and turned back over to pedestrians. Various activity hubs will dot both streets and offer free, family-friendly activities such as live music, buskers, art activities and much more. The fun runs between 10 am and 2 pm, then the cars, buses and streetcars return to the roads.

When: Bloor between Ossington and Yonge and Yonge between Bloor and Queen
Where: September 15

Queen West Art Crawl Outdoor Art Exhibition

While the bulk of the annual Queen West Art Crawl is aimed at adults, its outdoor art fair portion is decidedly family-friendly. The kids’ area will feature a variety of interactive art projects and a chance for your children to create alongside professional Toronto artists. There will also be live music, food trucks and, for the parents, a beer garden. Entry to the Exhibition is free but make sure your kids bring their allowance since there will be tons of cool items for sale.

When: September 21-22
Where: Trinity Bellwoods Park, 790 Queen St W

Harvest Day Celebration

Get your hands dirty at this afternoon event that will take place over in the Toronto Botanical Garden’s Teaching Garden, found on the west side of Wilket Creek Ravine. There you and your family can harvest vegetables for the food bank, plant garlic and ride something called the smoothie bike. While the event is free, advanced registration is recommended and note that parking at the Garden is paid.

When: September 21
Where: Toronto Botanical Garden, 777 Lawrence Ave E

The Word on The Street 

Canada’s largest literary festival is back for another weekend packed with books, magazine and music. This year take the family and hear Sharon and Bram (yes of “Skinnamarink” fame) on the concert stage, participate in an interactive science experiment over at TD KidStreet and pick up some new reading material from the marketplace. There will also be a comic creation workshop, tons of author readings and more.

When: Harbourfront Centre, 235 Queens Quay W
Where: September 22

Ontario Culture Days

This “national celebration of arts and culture” aims to “…invite the public to get hands-on and behind-the-scenes to highlight the importance of arts and culture in our communities.” Most events are family-friendly and this year’s Toronto events include indigenous art-making workshops, including one focused on making dreamcatchers, and a theatrical nature walk. Events are generally free, but some do require advanced registration.

When: September 27-29
Where: Assorted locations across Toronto

The Big Draw Festival

Take part in the world’s largest drawing festival while checking out one of Toronto’s historic homes. All 10 of the city’s museums, which include Colborne Lodge, Fort York National Historic Site and Todmorden Mills, will take part in this free, international event that invites your family to sketch, draw and paint their interpretation of this year’s theme, “Drawn To Life: Creativity and Wellbeing.”

When: September 28-29
Where: City of Toronto’s Historic Museum

Sick Kids Get Loud

Toronto is fortunate to be home to the amazing Sick Kids hospital. But all that awesomeness doesn’t come cheap. Help support this world-class institution by participating in this family-friendly fundraising event that starts with a walk through downtown Toronto and ends with a festival at Fort York. There, participants will take in live music by Serena Ryder and cover bands Dwayne Gretzky and The Mini Pop Kids, and will have access to all kinds of fun activities, including a BBQ lunch. Note that in order to access the festival, certain fundraising minimums need to be met. More info here

When: Saturday, September 28
Where: Downtown Toronto/Fort York


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