Above image: Detail of street art by artist Emily May Rose / Location: River & Shuter streets
What to do with kids and teens in Toronto in September 2025
September is like a great big reset button. While some may feel blah about back-to-school, this is the time of year that has me readjusting schedules and building fall to-do lists for the family in TOw. The new season is also a chance for me to refocus and set some ‘new year’s resolutions.’
So, no pumpkin lattes just yet, we are still squeezing out the last bit summer with these fall activities. Here’s our top ten list of things for your kids and teens in TOw this month:
1. NEIGHBOURHOOD FESTIVALS: Hand’s down, these are two of the best neighbourhood gatherings in the city. In the east, the Cabbagetown Festival offers something for everyone: artisan market right next to Riverdale farm, as well as a parade, street performers and games. September 6 & 7, Parliament and Carlton streets. FREE
In the west, the The Toronto Ukrainian Festival is North America’s largest Ukrainian street festival, with a massive parade, musical and dance performances and so much delicious food. September 12-14, Bloor West Village, FREE
2. MESSAGE ON THE WATER: The Water Lantern Festival is a community event where you and your family in TOw can write a note or personalize a lantern and set it onto the water. A ticket also gets you access to food trucks, live music, vendors, as well as the lantern launch. September 19 & 20, Downsview Park. TICKETED
3. ART ON THE LAKE: IT COMES IN WAVES, by Toronto artist and designer Ben Johnston, is an illuminated message of floating letters that shift with the wind, weather and waves. The installation is part of the Waterfront Toronto’s temporary floating art program. Check it out at night! On until early October, Harbour Square Basin. FREE
4. TERRY FOX RUN: It’s the 45th anniversary of the Terry Fox Run. More than 500 communities across the country participate and fundraise to help finish what Terry started. Find your local walk in T.O. September 14.
TRIP TIP: Get tickets to the special screening of the documentary Run Terry Run with the Toronto Sumphony Orchestra on November 10th, Roy Thomson Hall. TICKETED
5. CELEBRATING THAI FOOD AND CULTURE: Toronto’s Thai Fest takes over the iconic intersection, featuring 40+ food vendors, musical performances and DJs, plus spice challenges. Sankofa Square, September 20 & 21, FREE
6. COMEDY WITH TEENS: Second City’s cast and crew are currently presenting Duel Citizens, a comedy show full of satire, songs and improv. Take note parents in TOw: the show is rated R due to language and innuendo and kids 13 years and older are welcome (must be accompanied by an adult.) On until November, 90th MainStage Review. TICKETED
7. TIFF: The Toronto International Film Festival brings together movie lovers for date nights (and date mornings) over the course of 10 days. There is a great selection of films for the littles and teens in TOw, search ‘family friendly’ in the filter to find these and more: Little Amelie, Olmo, and Origin: The Story of the Basketball Africa League. Until September 14, around TOwn, TICKETED
8. MICHAEL JACKSON MUSICAL: MJ the Musical takes to the Toronto stage this month, showcasing the pop legend’s signature moves and music. Opens September 16, CAA Ed Mirvish Theatre. TICKETED
9. BACKYARD PLAYDATE: This is the final family-friendly PlayDate as part of Stackt’s backyard summer festival series. Families can expect live performances and singalongs, a family rave, plus giant inflatable art installations. September 20, Stackt Market, FREE
TRIP TIP: There is a mini basketball court too.
10. For the 19+ in TOw – 80s ROCK PARTY: Described as the ultimate immersion throwback party, Illumuniarium’s HOME BY 11 is a night of retro anthems by the likes of Journey, Bon Jovi and Madonna. Relive your MuchMusic dance party memories. September 19th, Distillery District. TICKETED
TRIP TIP: Head’s up that October’s edition is all about 90s Pop: Destiny’s Child, Backstreet Boys and NSYNC.)
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