September 10th to 20th – Toronto International Film Festival

Toronto International Film Festival returns with world premieres, red carpets, screenings, industry events, talks, and public programming. TIFF is one of the world’s leading film festivals and a major cultural event in Toronto.

Where: Various Locations in Toronto

When: September 10th to 20th,

Admission: Paid and Free Events

(Film Festival)

September 17th – Give Me Liberty Street Party

Give Me Liberty Street Party brings food, music, drinks, vendors, entertainment, and community energy to Liberty Village. The annual neighbourhood street party celebrates local businesses and community culture.

Where: Lamport Stadium parking lot, 75 Fraser Avenue, Toronto

When: September 17th, 4:00 pm – 11:00 pm

Admission: Free

(Street Party)

September 17th – LP – All Is Not Lost Tour

Singer-songwriter LP brings the All Is Not Lost Tour to Toronto for an evening of powerful vocals, emotional songwriting, and fan-favourite tracks.

Where: Massey Hall, Toronto

When: September 17th, 8:00 pm

Admission: Ticketed. Grab your tickets here

(Concert)

September 17th to 20th – Brampton Fall Fair

Brampton Fall Fair returns with agricultural traditions, family attractions, food, entertainment, and seasonal activities for a classic fall fair experience.

Where: Brampton Fairgrounds

When: September 17th to 20th

Admission: Ticketed. Prices start at $20. Grab your tickets here

(Fall Fair)

September 18th to 20th – ArtWalk in the Square

ArtWalk in the Square brings artists, makers, galleries, and original works to CF Shops at Don Mills for a weekend of outdoor art, shopping, and community engagement.

Where: CF Shops at Don Mills, Toronto

When: September 18th to 20th,

• September 18th, 3:00 pm – 8:00 pm

• September 19th, 10:00 am – 7:00 pm

• September 20th, 11:00 am – 5:00 pm

Admission: Free

(Art Fair)

September 18th to October 4th – Ontario Culture Days 2026

Ontario Culture Days launches with arts, culture, workshops, performances, exhibitions, and community programming across the province, including events throughout Toronto.

Where: Various Locations in Ontario

When: September 18th to 20th,

(Arts Festival)

September 18th and 19th – Afrocan Roots and Rhythms Fest

Afrocan Roots and Rhythms Fest celebrates African and Caribbean culture through music, dance, food, vendors, performances, and community programming.

Where: Celebration Square, Mississauga

When:

September 18th, 2:00 pm – 11:00 pm

September 19th, 12:00 pm – 11:00 pm

Admission: Free

(Cultural Festival)

September 18th and 19th – Public Pier Toronto

This fall, one of Toronto’s most distinctive waterfront sites will be transformed into Public Pier, a free cultural experience featuring public art, live music, food, dance and immersive nighttime projections.

Where: Marina Quay West, 539 Queens Quay West, Toronto

When: September 18th and 19th

• Fridays, 6:00 pm. to 11:00 pm

• Saturdays, 6:00 pm. to 11:00 pm

Admission: Free

(Art and Cultural Experience)

September 18th to 20th – Toronto Ukrainian Festival

Toronto Ukrainian Festival returns to Bloor West Village with Ukrainian food, music, dance, vendors, performances, community programming, and cultural celebration.

Where: Bloor Street West, between Jane Street and Glendonwynne Road, Toronto

When: September 18th to 20th,

• September 18th, 5:00 pm – 11:00 pm

• September 19th, 9:30 am – 11:00 pm

• September 20th, 10:00 am – 7:00 pm

Admission: Free

(Cultural Festival)

September 18th to 20th – Kensington Market Jazz Festival

Kensington Market Jazz Festival brings live jazz performances to venues, streets, and spaces throughout one of Toronto’s most iconic neighbourhoods. The festival showcases local musicians, intimate concerts, and community-based music programming.

Where: Kensington Market, Toronto

When: September 18th to 20th

Admission: Ticketed

(Music Festival)

September 18th to 20th – Water Lantern Festival

Water Lantern Festival is a family friendly event that allows guests to witness the beauty of thousands of lanterns and the lights reflecting upon the water on an emotional and unforgettable night.

Where: Downsview Park, 70 Canuck Ave, North York

When: September 18th to 20th, 4:30 pm

Admission: Ticketed. Prices start at $42. Grab your tickets here

(Lantern Festival)

September 19th – Smoke-A-Palooza

Smoke-A-Palooza brings barbecue, smoked food, vendors, entertainment, and community celebration to Sankofa Square. The food-focused festival is designed for visitors looking to enjoy smoky flavours and outdoor festival energy.

Where: Sankofa Square, Toronto

When: September 19th, 11:00 am – 11:00 pm

Admission: Free

(Food Festival)

September 19th – Cake Picnic Toronto

This September, Toronto’s ultimate gathering for cake lovers returns as Cake Picnic Toronto takes over downtown Toronto on September 19th.

Where: Downtown Toronto

When: September 19th, 10:00 am – 2:00 pm

Admission: Ticketed. Prices start at $45. Grab your tickets here

(Food Event)

September 19th – Celtic Island Music Festival

Celtic Island Music Festival brings Celtic-inspired music and live performances to Toronto Island for an afternoon of music and community by the waterfront.

Where: The Toronto Island BBQ & Beer Company

When: September 19th, 12:00 pm – 7:00 pm

Admission: Free

(Cultural Festival)

September 19th – Brampton Latin Festival

Brampton Latin Festival celebrates Latin culture with music, dance, food, vendors, performances, and family-friendly programming.

Where: Gage Park, Brampton

When: September 19th, 12:00 pm – 10:00 pm

Admission: Free

(Cultural Celebration)

September 19th – AppleFest

AppleFest celebrates fall flavours, family activities, food, vendors, heritage programming, and apple-themed experiences at Markham Museum.

Where: Markham Museum, Markham

When: September 19th, 10:00 am – 5:00 pm

Admission: Free

(Apple Festival)

September 19th – Annual RBC Race For The Kids

RBC hosts a global race initiative that brings communities together to run, walk, and wheel in support of youth charities

Where: Mel Lastman Square, 5100 Yonge St, North York

When: September 19th, 8:00 am – 12:00 pm

Admission: Free

(Race)

September 19th – Toronto Maple Leafs vs. Montreal Canadiens

Toronto Maple Leafs take on Montreal Canadiens at the Scotiabank Arena

Where: Scotiabank Arena

When: September 19th, 7:00 pm

Admission: Ticketed

(NHL Game)

September 19th and 20th – Roncesvalles Polish Festival

Roncesvalles Polish Festival returns with Polish food, music, dance, vendors, patios, performances, and community programming along Roncesvalles Avenue. The festival celebrates Polish culture and the neighbourhood’s local businesses.

Where: Roncesvalles Avenue, from Queen Street West to Dundas Street West, Toronto

When: September 19th and 20th,

• September 19th, 11:00 am – 11:00 pm

• September 20th, 11:00 am – 7:00 pm

Admission: Free

(Cultural Festival)

September 19th and 20th – Queen West Art Crawl

Queen West Art Crawl returns to Trinity Bellwoods Park with artists, makers, live programming, and opportunities to discover and support local creative talent.

Where: Trinity Bellwoods Park.

When: September 19th and 20th, 11:00 am – 6:00 pm

Admission: Free

(Cultural Festival)

September 19th and 20th – Canadian Pet Expo

Canadian Pet Expo brings pet lovers together for a weekend of animal-focused exhibits, vendors, demonstrations, products, and family-friendly experiences.

Where: The International Centre, 6900 Airport Road, Mississauga

When: September 19th and 20th,

• September 19th, 10:00 am – 5:00 pm

• September 20th, 10:00 am – 4:00 pm

Admission: Free

(Cultural Festival)

September 19th and 20th – The National Franchise Show

The National Franchise Show connects aspiring entrepreneurs and business owners with franchise opportunities, industry professionals, and resources for starting or expanding a business.

Where: The International Centre, Hall 5, Mississauga

When: September 19th and 20th, 11:00 am – 5:00 pm

Admission: Ticketed. Prices start at $15. Grab your tickets here

(Cultural Festival)

September 19th and 20th – The Endy Ice Box

This weekend, Canadian premier sleep brand Endy is partnering with Toronto ice cream shop Ruru Baked to bring the Endy Ice Box, a free two-day pop-up on September 19th and 20th.

Where: September 19th and 20th, 12:00 pm – 5:00 pm

When:

• September 19th (937 Queen St W, Toronto)

• September 20th (1829 Queen St E, Toronto)

Admission: Free

September 20th – Terry Fox Run Toronto – Beaches

The Terry Fox Run brings the Toronto Beaches community together to run, walk, and raise funds in support of cancer research while honouring Terry Fox’s legacy.

Where: Woodbine Beach, 1675 Lakeshore Blvd E, Toronto

When: September 20th, 9:00 am

Admission: Free to Attend. Register Here

(Race)

September 20th – Anatolia Fest

Anatolia Fest celebrates Turkish and Anatolian culture through food, music, dance, vendors, performances, and community programming. The free festival brings cultural celebration to Sankofa Square.

Where: Sankofa Square, Toronto

When: September 20th, 12:00 pm – 8:00 pm

Admission: Free

(Cultural Festival)

September 20th – Richmond Hill ArtWalk

Richmond Hill ArtWalk showcases artists, makers, galleries, and creative vendors in a free outdoor art market setting.

Where: Richmond Hill Centre for the Performing Arts area, Richmond Hill

When: September 20th, 11:00 am – 5:00 pm

Admission: Free

(Art Market)

September 20th – 2026 Long Branch Tree Fest

Long Branch Tree Fest celebrates Toronto’s urban forest with community programming, environmental education, family-friendly activities, and a day outdoors at Marie Curtis Park.

Where: Marie Curtis Park, 2 Forty-Second Street, Etobicoke

When: September 20th, 12:00 pm – 4:00 pm

Admission: Free

(Community Festival)

September 20th – Thee Sacred Souls x LA LOM: The Constellation Tour

Enjoy an evening of soulful melodies, retro-inspired sounds, and captivating performances from Thee Sacred Souls and LA LOM.

Where: RBC Amphitheatre

When: September 20th, 6:30 pm

Admission: Ticketed. Grab your tickets here

(Concert)

September 20th and 21st – Toronto Cha Raja

Toronto Cha Raja is a vibrant arts, culture, and community festival celebrating South Asian traditions through music, dance, food, workshops, cultural experiences, dhol-tasha, kids’ activities, artisan vendors, and live performances. The free community festival brings together families, youth, artists, and multicultural communities in a lively and inclusive atmosphere at the heart of North York.

Where: Mel Lastman Square, Toronto

When: September 20th and 21st,

Admission: Free

(Cultural Festival)