45+ Fun Things to do In Toronto This September

Hungry 416
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Alright, folks, gather ’round! September’s rolling in, and Toronto’s about to turn up the charm. We’re talking crisp air, vibrant foliage, and a city brimming with energy.  Whether you’re a local looking for a fresh adventure or a visitor eager to experience the best things to do in Toronto this September, this month’s got something special in store.

45+ Fun Things to do In Toronto This September

1. Taste The Caribbean (September 1-2)

September kicks off with a bang, bringing the vibrant flavours of the Caribbean to Toronto. Imagine jerk chicken sizzling on the grill, the aroma of roti filling the air, and the rhythmic beats of Caribbean music setting the mood. It’s a feast for the senses, a celebration of culture, and a perfect way to say goodbye to summer.

2. Toronto International Film Festival 2024 (September 5 – 15)

Calling all movie buffs! TIFF is back, transforming Toronto into a global cinema hub. Rub shoulders with celebrities, catch premieres of the hottest films, and immerse yourself in the world of storytelling. Whether you’re into blockbusters or indie gems, TIFF has it all.

  • Location:
    • Canadian Broadcasting Centre
    • Roy Thomson Hall
    • Royal Alexandra Theatre
    • Scotiabank Theatre Toronto
    • TIFF Lightbox
    • TIFF Lightbox, 6th Floor
    • VISA Screening Room At The Princess Of Wales Theatre
  • Category: Date or Friends / 19+
  • Admission: Ticket prices vary
  • Website: https://tiff.net/about-the-festival

3. Asialicious Carnival (September 6-8)

Asialicious Carnival
Photo via AsialiciousTO 2024 | 多倫多亞太美食節

Asialicious Carnival is a foodie’s paradise, showcasing the diverse and delicious flavours of the continent. From steaming dumplings to fragrant curries, your taste buds are in for a treat. And with live music and cultural performances, it’s a full-on celebration.

4. Drive Festival (September 6-8)

Calling all car enthusiasts! The Drive Festival is a showcase of automotive excellence, featuring classic cars, supercars, and everything in between. It’s a chance to admire stunning vehicles, learn about automotive history, and maybe even catch a glimpse of your dream car.

  • Location: Canadian Tire Motorsport Park
  • Category: Family-Friendly / Date or Friends
  • Admission: Starts at $18
  • Website: https://drivefestival.com

5. Taste of North York (September 6-8)

North York’s culinary scene takes centre stage at this delicious festival. Sample dishes from local restaurants, discover hidden gems, and expand your palate. With live music and family-friendly activities, it’s a great way to spend a day exploring the neighbourhood.

6. Taste of the Kingsway (September 6-8)

Step back in time at this charming street festival. The Taste of the Kingsway celebrates the neighbourhood’s history with classic cars, vintage vendors, and live entertainment. It’s a nostalgic trip down memory lane, perfect for families and anyone who loves a good old-fashioned community gathering.

7. Ube Wonderland (September 6-8)

Calling all dessert lovers! Ube Wonderland is a celebration of this vibrant purple yam, featuring everything from ube ice cream to ube cheesecakes. It’s a sweet and colourful experience that’ll leave you wanting more.

8. Cabbagetown Festival 2024 (September 7)

Cabbagetown Festival 2024
Photo via Cabbagetown BIA

Picture this: strolling down tree-lined streets, admiring Victorian homes, and stumbling upon a vibrant street festival. That’s the Cabbagetown Festival in a nutshell. It’s a celebration of community, featuring live music, local artisans, and a charming atmosphere that’ll make you feel right at home.

9. Taste of the Junction (September 7)

Taste of the Junction showcases the neighbourhood’s diverse food scene, offering everything from gourmet bites to comfort food classics. It’s a foodie’s dream come true.

10. Queen St. Marketplace – Rosedale (September 7)

Calling all shopaholics! Queen St. Marketplace is a curated market featuring local artisans, vintage finds, and unique treasures. It’s the perfect place to discover one-of-a-kind gifts or treat yourself to something special.

11. Toronto Vegandale Festival (September 7)

Vegans and vegetarians, rejoice! The Toronto Vegandale Festival is a celebration of all things plant-based, featuring delicious food, ethical vendors, and inspiring talks. It’s a chance to discover new flavours, connect with like-minded people, and learn about sustainable living.

12. World Of Jazz Festival (September 6-8)

Let the music move you at this vibrant jazz festival. World Of Jazz Festival showcases talented musicians from around the globe, filling the city with soulful melodies and infectious rhythms. Whether you’re a jazz aficionado or simply love a good beat, this festival will get your toes tapping.

  • Location: Downtown Brampton, Garden Square
  • Category: Family-Friendly / Date or Friends / 19+ 
  • Admission: Free
  • Website: https://www.worldofjazz.ca 

13. Trinbago Toronto Festival (September 7-8)

Get ready to immerse yourself in the vibrant culture of Trinidad and Tobago. The Trinbago Toronto Festival is a celebration of Caribbean heritage, featuring colourful costumes, lively music, and mouthwatering food. It’s a chance to experience the island spirit right here in Toronto.

  • Location: Nathan Phillips Square
  • Category: Family-Friendly / Date or Friends 
  • Admission: FREE
  • Website: https://www.trinbago.ca 

14. West Niagara Fair (September 6-8)

Step into a world of agricultural wonders and family-friendly entertainment. The West Niagara Fair features livestock shows, midway rides, live music, and delicious fair food. It’s a classic fall tradition that’ll bring out the kid in everyone.

15. Brampton Fall Fair (September 12-15)

Celebrate the harvest season at this beloved community event. The Brampton Fall Fair features agricultural exhibits, live entertainment, midway rides, and a whole lot of fun. It’s a chance to connect with nature, learn about farming, and create lasting memories with loved ones.

16. ArtWalk in the Square (September 13-15)

ArtWalk in the Square showcases the work of talented local artists, offering a chance to admire stunning creations and perhaps even take home a piece of your own. It’s a feast for the eyes and a celebration of creativity.

17. Bloor West Village Toronto Ukrainian Festival (September 13-15)

The Bloor West Village Toronto Ukrainian Festival features traditional music, dance, food, and crafts. It’s a chance to learn about Ukrainian heritage, connect with the community, and enjoy a lively celebration.

  • Location: Bloor Street West, between Jane Street and Runnymede Road 
  • Category: Family-Friendly / Date or Friends 
  • Admission: Free
  • Website: https://ukrainianfestival.com 

18. Toronto Waterfront Festival 2024 (September 14-15)

Bask in the beauty of Lake Ontario while enjoying a vibrant festival atmosphere. The Toronto Waterfront Festival offers live music, food trucks, artisan vendors, and stunning views. It’s the perfect way to soak up the last days of summer by the water.

  • Location: Sugar Beach (11 Dockside Dr, Toronto)
  • Category: Family-Friendly / Date or Friends 
  • Admission: Free
  • Website: https://towaterfrontfest.com 

19. Roncesvalles Polish Festival (September 14-15)

Get ready for a lively celebration of Polish heritage. The Roncesvalles Polish Festival features traditional music, dance, food, and a warm, welcoming atmosphere. It’s a chance to experience a different culture and perhaps even learn a few Polish dance moves!

  • Location: Roncesvalles Village
  • Category: Family-Friendly / Date or Friends 
  • Admission: Free
  • Website: https://polishfestival.ca 

20. Philippine Festival Mississauga (September 14-15)

Experience the vibrant culture of the Philippines at this colourful festival. The Philippine Festival Mississauga showcases traditional music, dance, food, and crafts. It’s a chance to celebrate Filipino heritage and connect with the community.

21. Craft Beverage Festival (September 14)

Calling all craft beer, wine, and spirits enthusiasts! Head for the Hills is a celebration of local beverages, featuring tastings, food pairings, and live music. It’s a chance to discover new favourites and support local producers.

22. Uxbridge Art on the Fringe Festival (September 14-15)

Step into a world of artistic expression at this unique festival. Uxbridge Art on the Fringe showcases visual and performing arts in unconventional spaces, creating a truly immersive experience. It’s a chance to discover hidden talents and be inspired by the power of art.

23. 2024 TORONTO PIN & PATCH SHOW (September 14)

Calling all collectors and pop culture enthusiasts! The Toronto Pin & Patch Show is a haven for enamel pin and patch lovers, featuring vendors from across North America. It’s a chance to add to your collection, discover unique designs, and connect with fellow enthusiasts.

  • Location: Parkdale Hall (1605 Queen St W)
  • Category: Family-Friendly / Date or Friends 
  • Admission: General admission is Free. VIP admission is available. 
  • Website: https://www.pinandpatchshow.com 

24. Annual T.O. Webfest (September 17-18)

Calling all web series fans! The Annual T.O. Webfest showcases the best in digital storytelling, featuring screenings, panels, and awards. It’s a chance to discover new talent, connect with creators, and celebrate the ever-evolving world of web series.

  • Location: Novotel Toronto Center (45 The Esplanade, Toronto)
  • Category: Date or Friends / 19+ 
  • Admission: Starts at $12.77
  • Website: https://towebfest.ca 

25. Ancaster Fair (September 19-22)

Get ready for a classic fall tradition! The Ancaster Fair features agricultural exhibits, thrilling midway rides, live entertainment, and all your favourite fair food. It’s a wholesome, family-friendly experience that’ll leave you with a smile.

  • Location: 630 Trinity Road South, Jerseyville, Ontario
  • Category: Family-Friendly 
  • Admission: Starts at $5
  • Website: https://www.ancasterfair.ca

26. Common Ground Dance Festival (September 19-21)

Let the music move you at this dynamic dance festival. Common Ground Dance Festival showcases contemporary dance performances, workshops, and installations, pushing the boundaries of movement and expression. It’s a chance to experience the power and beauty of dance.

27. world of literature at the Toronto International Festival of Authors (September 19-29)

Bookworms, unite! The Toronto International Festival of Authors is a literary lover’s dream, featuring readings, talks, and workshops with renowned authors from around the world. It’s a chance to discover new books, meet your favourite writers, and celebrate the power of storytelling.

  • Location:  235 Queens Quay West, Toronto
  • Category: Family-Friendly / Date or Friends 
  • Admission: Starts at $15.99
  • Website: https://festivalofauthors.ca 

28. Gallery Weekend Toronto (September 19-22)

Art enthusiasts, this one’s for you! Gallery Weekend Toronto is a city-wide celebration of contemporary art, featuring exhibitions, talks, and special events at galleries across Toronto. It’s a chance to discover new artists, engage with the art community, and be inspired by the creative energy of the city.

  • Location: Various galleries across Toronto 
  • Category: Family-Friendly / Date or Friends 
  • Admission: Free
  • Website: https://galleryweekend.ca 

29. Le Diner en Blanc (September 10) 

Prepare for an unforgettable evening of elegance and mystery. Le Diner en Blanc is a pop-up picnic where guests dress in all white and gather at a secret location for a magical night of dining and dancing under the stars. It’s a unique and exclusive experience that’ll leave you feeling enchanted.

  • Location: Secret location 
  • Category: 19+ 
  • Registration takes place in 3 phases:
  • Members from the previous year & friends of the organizers.
  • Friends “sponsored” by Phase 1 members.
  • General Public that signed up on the official website.
  • Website: https://toronto.dinerenblanc.com 

30. Ontario Culture Days (September – OctOBER 13)

Get ready to celebrate the vibrant arts and culture scene in Ontario! Ontario Culture Days offers a plethora of free events and activities, from interactive workshops and behind-the-scenes tours to live performances and exhibitions. It’s a chance to explore your creative side and discover hidden gems across the province.

  • Location: Various locations across Ontario 
  • Category: Family-Friendly / Date or Friends 
  • Admission: Free
  • Website: https://culturedays.ca/en/on 

31. Bolton Fall Fair (September 20-22)

Experience the charm of a traditional fall fair. The Bolton Fall Fair features agricultural exhibits, thrilling midway rides, live entertainment, delicious food, and a whole lot of family fun. It’s the perfect way to celebrate the harvest season and create lasting memories.

32. TORONTO WATER LANTERN FESTIVAL (SEPTEMBER 20

Experience a magical evening at the Toronto Water Lantern Festival. Witness thousands of lanterns illuminating the night sky, enjoy live music and food trucks, and connect with your community. It’s a celebration of light, hope, and happiness.

33. Queen West Art Crawl (September 21-22)

Immerse yourself in the vibrant art scene of Queen West. The Queen West Art Crawl features open studios, pop-up galleries, live music, and street performances. It’s a chance to discover local talent, admire unique creations, and experience the artistic pulse of the neighbourhood.

34. Cranberry Harvest (September 21 – October 27)

Get ready for a berry good time! The Cranberry Harvest offers a unique opportunity to witness the cranberry harvest firsthand, learn about the process, and enjoy cranberry-themed treats. It’s a fun and educational experience for the whole family.

35. VegTO Fest (September 21-22)

Calling all vegans, vegetarians, and anyone curious about plant-based living! VegTO Fest is a celebration of all things vegan, featuring delicious food, ethical vendors, and inspiring talks. It’s a chance to discover new flavours, connect with like-minded people, and learn about sustainable living.

36. Toronto Biennial of Art (September 21) 

Expand your artistic horizons at this thought-provoking exhibition. The Toronto Biennial of Art showcases contemporary art from around the world, exploring themes of social justice, environmental awareness, and cultural identity. It’s a chance to engage with challenging and inspiring works of art.

  • Location: 32 Lisgar Street, in the heart of West Queen Street West
  • Category: Family-Friendly / Date or Friends 
  • Admission: Free
  • Website: https://torontobiennial.org

37. Sabrina Carpenter Live In Toronto (September 25)

Calling all pop music fans! Sabrina Carpenter is taking the stage in Toronto, bringing her catchy tunes and infectious energy to the city. It’s a chance to sing along to your favourite songs and experience a night of unforgettable music.

38. Venus Fest (September 26-28)

Venus Fest is a music festival dedicated to showcasing and celebrating female and non-binary artists. It’s a chance to discover new talent, support diverse voices, and enjoy a weekend of empowering music.

  • Location: Monarch Tavern
  • Category: 19+ 
  • Admission: Ticket prices vary
  • Website: https://venusfest.net 

39. Fall for Dance North (FFDN) (September 26- October 6)

Fall for Dance North presents a diverse program of contemporary dance performances, showcasing both established and emerging artists. It’s a chance to experience the beauty and power of movement.

  • Location: Meridian Hall 
  • Category: Family-Friendly / Date or Friends 
  • Admission: Starts at $15 
  • Website: https://www.ffdnorth.com 

40. Art Bash 2024 (September 26)

Get your creative juices flowing at this interactive art event. Art Bash features live art demonstrations, hands-on workshops, and a vibrant atmosphere. It’s a chance to explore different art forms, express yourself, and connect with fellow art enthusiasts.

41. Kitchener-Waterloo Oktoberfest (September 27 – October 19)

Get ready to experience a taste of Bavaria right here in Ontario! Kitchener-Waterloo Oktoberfest is a lively celebration of German culture, featuring traditional food, beer, music, and dancing. Don your lederhosen or dirndl and join the festivities!

  • Location: Kitchener-Waterloo 
  • Category: Family-Friendly / Date or Friends / 19+ 
  • Admission: Varies by location
  • Website: https://www.oktoberfest.ca 

42. Toronto Hungarian Film Festival 2024 (September 27 – 29)

Discover the rich world of Hungarian cinema at this film festival. The Toronto Hungarian Film Festival showcases a selection of contemporary and classic Hungarian films, offering a glimpse into Hungarian culture and storytelling.

  • Location: Carlton Cinema, 20 Carlton St., Toronto
  • Category: Date or Friends / 19+ 
  • Admission: Starts from $12
  • Website: https://www.tohuff.com 

43. Riverside Art Show and Sale (September 27-29)

Discover the talent of local artists at this charming art show and sale. The Riverside Art Show and Sale features a variety of mediums, from paintings and sculptures to jewellery and textiles. It’s a chance to support local artists and find unique pieces to adorn your home or wardrobe.

  • Location: 361 Danforth Ave Toronto
  • Category: Family-Friendly / Date or Friends 
  • Admission: Free

44. Mimico Food Fest (September 21)

Foodies, get ready to indulge! The Mimico Food Fest is a culinary celebration featuring a diverse array of local food vendors, offering everything from savoury treats to sweet delights. It’s the perfect opportunity to discover new flavours and support local businesses.

45. Word on The Street Toronto (September 28-29)

The Word on The Street Toronto is a literary festival celebrating books, magazines, and the power of storytelling. Explore exhibitor booths, attend author readings, and participate in interactive workshops. It’s a fantastic opportunity to discover new reads and connect with fellow book enthusiasts.

46. YMCA Charity 5K Run (September 28)

Lace up your running shoes and support a worthy cause! The YMCA Charity 5K Run is a fun and active way to give back to the community. Whether you’re a seasoned runner or a casual jogger, this event welcomes all fitness levels.

47. Toronto Oktoberfest (September 27-28)

Experience the spirit of Oktoberfest without leaving Toronto! The Toronto Oktoberfest features traditional German food, beer, music, and dancing. Don your lederhosen or dirndl and join the festivities!

48. Love Festival – Taste of Southeast Asia (September 28-29)

Get ready to immerse yourself in the vibrant tapestry of Southeast Asian culture at the Love Festival! This two-day extravaganza promises a feast for the senses, showcasing the very best of the region’s food, music, fashion, and talent.

  • Location: 300 City Centre Dr Mississauga
  • Category: Family-Friendly / Date or Friends 
  • Admission: Free
  • Website: www.tastesofsea.com

49. Toronto Garlic Festival (September 29)

Garlic lovers, this one’s for you! The Toronto Garlic Festival is a celebration of all things garlic, featuring delicious food, cooking demonstrations, and local vendors selling garlic-themed products. It’s a chance to experience the versatility of this flavorful bulb and discover new ways to incorporate it into your cooking.

  • Location: Streetfest On Spadina Road between Davenport Rd & Dupont St
  • Category: Family-Friendly / Date or Friends 
  • Admission: Free
  • Website: https://torontogarlicfestival.ca 

50. Halloween Haunt (September 27 to November 2)

Brace yourself for a terrifyingly fun night as Canada’s Wonderland transforms into a scream park filled with haunted mazes, scare zones, monstrous creatures, and thrilling night rides. This is the ultimate Halloween event for thrill-seekers and horror fans!

With this final roundup of events, it’s clear that September in Toronto is an absolute feast for the senses! Whether you’re into food, literature, art, music, or simply enjoying the outdoors, there’s something for everyone. So, what are you waiting for? Get out there and experience the magic of Toronto this September!

References:

Hungry 416 is your go-to guide for the best things to do, eats, travel, and entertainment in Toronto and Ontario! We curate top restaurants, must-try activities, and hidden gems that make this region so vibrant and exciting.

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