September’s here, and that means it’s a time of excitement here in our city. From the start of fall and spooky season to festivals galore (hello, TIFF!), there are tons of incredible things to do in Toronto this September.

Summer will soon be history, but don’t worry, the fun is far from over.

Here’s your guide to the very best things to do in Toronto this September.

Now, go ahead and have the best time ever. You deserve it!

Outdoor Events & Festivals

The Cabbagetown Festival

After a four-year hiatus, one of Toronto’s longest-running street festivals makes a return.

The Cabbagetown Festival kicks off this month with a fun-filled weekend of food, entertainment, and shopping.

Since being founded in 1976, The Cabbagetown Festival is considered one of the city’s longest-running and most beloved street festivals.

And with its comeback, we can only expect it to be huge!

When: September 9th & 10th, 2023
Where: Parliament Street, Gerrard Street to Wellesley Street, Carlton Street to Ontario Street

Pedestrian Sundays at Kensington Market

The Sunday street parties we know and love are back at Kensington Market.

Pedestrian Sundays is returning for its second edition this season and will continue well into the fall.

The sounds of live music and smells of street food will fill the air and visitors will be treated to live performances, entertainment, art showcases, and displays from local creators.

When: September 24th & October 29th, 2023
Where: Kensington Market

Sponsored Pick: Monsoon Sound, This Is Brampton Showcase & Flow Fest

To commemorate another epic summer in the city, Brampton On Stage is bringing 3 epic festivals full of with rhythm and good vibes. Monsoon Sound and Flow Fest celebrate sounds from all around the world, with South Asian Hip Hop beats and Afro-Caribbean and Jazz fusions to make this September a memorable one. Plus don’t miss the first annual This is Brampton Showcase.

When: Monsoon Sound – Friday, September 8 at 7 PM. This Is Brampton Showcase – Thursday, September 14 at 8 PM. Flow Fest – Saturday, September 23 at 7:30 PM.
Where: The Rose – 1 Theatre Lane, Brampton
Cost: click here for ticket prices

Canadian National Exhibition

Toronto’s beloved late-summer carnival is officially back, and as you’d expect, the food and drinks are completely over the top!

The annual fair has new attractions and performances this year, including a Las Vegas-style fountain show and North America’s tallest travelling Ferris wheel.

Live music and entertainment will be performed across seven stages, and of course, the fair is filled with rides, games, and carnival eats galore!

When: Until September 4th, 2023
Where: Exhibition Place

Nuit Blanche Toronto

Nuit Blanche is back! The famous city-wide art celebration will run all night long on September 23rd.

There’s a lot to look forward to at this year’s Nuit Blanche. Art installations and interactive experiences will take place from 7 PM to 7 AM in every corner of the city.

Nuit Blanche is completely free to attend and will feature more than 80 art projects from close to 250 artists from a variety of disciplines.

When: September 23rd, 2023, 7 PM to 7 AM
Where: See all exhibitions and installations

Hot and Spicy Festival

This festival is a celebration of all things India and will bring together the best of Indian arts, food, music, and culture.

Music lovers are in for a treat as various performers take the stage to showcase their contemporary, traditional, and fusion sounds.

The Hot and Spicy Festival will also showcase the diverse culinary culture of India. From aromatic curries to sizzling street food, there’s something to satisfy every craving.

When: September 1st to 4th, 2023
Where: Harbourfront Centre

Electric Island

Toronto’s beloved outdoor concert and picnic series is back this September.

This year’s festival is back for its 11th year and bigger than ever with eight days of music throughout the spring and summer.

Electric Island held its opening weekend back in May and we still have one more weekend to look forward to this year!

When: September 2nd & 3rd, 2023
Where: Woodbine Park, 1695 Queen Street East

Music on the River

Boating, music, warm nights — put ’em all together and you have what might just be the coolest live concert experience Toronto has to offer.

Music on the River is a concert series right on the Humber River and you’ll get to paddle your way to the show.

Your ticket comes with a boat rental, paddle, lifejackets, access to the show, and a glowstick to wave along with the music.

When: Various dates until October 2023
Where: Humber River Paddling Centre, 9 Old Mill Rd

The Toronto Waterfront Festival

The quack is back this September for our last hurrah of the summer on the water.

Toronto’s annual Waterfront Festival will have a special returning guest this year — the world’s largest rubber duck!

The duck will be stationed at 7 Queen’s Quay for all to enjoy, and the festival will feature all kinds of fun programming, activities, and entertainment.

When: September 16th & 17th, 2023
Where: 7 Queen’s Quay West, Toronto

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SummerSeries in Trillium Park

A summer-long event is back at Trillium Park and it’s free for visitors of all ages.

This park on the waterfront is the perfect spot to enjoy music, arts, wellness, and nature.

Featuring Ontario-based and international artists, this season’s program features cultural events, live musical performances, and outdoor yoga classes.

When: Until late September 2023
Where: Trillium Park, 955 Lake Shore Boulevard West

Toronto Council Fire Indigenous Legacy Gathering

This September 30th marks the National Day for Truth and Reconciliation in Canada.

If you plan to participate, head down to Nathan Phillips Square for an annual two-day Indigenous Legacy Gathering, dedicated to showcasing and supporting Indigenous culture, tradition, and arts.

Put on by the Toronto Council Fire Native Cultural Centre, this event will feature Indigenous presentations, performances, workshops, food vendors, artisans, and more.

When: September 29th & 30th, 2023
Where: Nathan Phillips Square

Toronto Dragon Festival

It’s time to celebrate 3,000 years of Chinese art and culture right here in the city!

The annual Toronto Dragon Festival will bring all kinds of entertainment to Nathan Phillips Square this month, including a dazzling water show, dragons, Kung-Fu, acrobatics, fashion, and dance.

Plus, delicious food, of course!

When: September 1st to 3rd, 2023
Where: Nathan Phillips Square

Canadian International Air Show

Eyes to the skies, Toronto! The Canadian International Air Show (CIAS) is returning for another epic display above the city this Labour Day weekend.

Known as Canada’s largest and longest-running air show, the CIAS will be celebrating the 51st season of our beloved Canadian Forces Snow Birds.

The event is described as a “jam-packed air display showcasing modern military jets, vintage warbirds, [and] thrilling aerobatics” featuring a lineup of amazing performers.

When: September 2nd to 4th, 2023
Where: See location map here

The Queen West Art Crawl

The annual two-day arts festival in Trinity Bellwoods Park is making a comeback this September for its “roaring 20th” anniversary!

This beloved event is in support of artists and residents in Toronto through art, music, and multiculturalism.

The inclusive arts and multicultural festival will feature an outdoor art exhibition, 2SLGBT+ friendly Kids’ Zone and a Main Stage with music and drag that is 50%+ BIPOC.

Come out and celebrate Toronto’s local talent and diversity!

When: September 23rd & 24th, 2023
Where: Trinity Bellwoods Park

Bloor West Village Toronto Ukrainian Festival

Said to be the largest Ukrainian festival in North America, this annual event will take place in Bloor West Village this September.

The neighbourhood-wide event will be a celebration of Ukrainian culture, heritage, and the community’s history in Canada.

It will feature a range of traditional performances, youth performers, live music, dance, food, and activities.

When: September 15th to 17th, 2023
Where: Bloor West Village

Roncesvalles Polish Festival

The annual celebration of culture, art, and music is returning to Roncesvalles this September, in tribute to the neighbourhood, its history, and the people who call it home.

This year, visitors can look forward to fan favourites like Polka and pierogi, local artists, musicians and, of course, food.

There will be countless vendors, exhibitors, buskers, and live performances at four separate stages. It’s going to be spectacular!

When: September 16th & 17th, 2023
Where: Roncesvalles Avenue


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Food & Drink Events

The Taste of the Kingsway

It’s the 50th anniversary of south Etobicoke’s largest street festival.

Get ready to dance, sip, snack, and celebrate all weekend long with midway rides, family-friendly activities, games, performances, music, and tasty food.

When: September 8th to 10th, 2023
Where: Bloor Street West from Prince Edward Drive to Montgomery Street

Smorgasburg Toronto

Attention, foodies of Toronto! The largest weekly open-air food market in America, Smorgasburg, is gracing our waterfront for the second summer in a row.

The market, which is popular in cities like Brooklyn, LA, and Miami, is back in Toronto every Saturday until early September.

Admission to the “food flea market” is free and there are over 50 hand-picked vendors on-site showcasing their delicious cuisine.

When: Every Saturday until September 9th, 2023, 11 AM to 6 PM
Where: Captain John’s Pier, 7 Queens Quay East

VegTO Fest

Calling all veg heads! The VegTO festival is back – Toronto’s only free vegan festival.

Here you’ll get to experience over 200 exhibitors offering food, wares and other wonders, all in support of a vegan and vegetarian lifestyle.

Mingle with like-minded folks and learn all about the fresh ideas of innovators in the plant-based space.

When: September 9th & 10th, 11 AM to 6 PM
Where: Nathan Phillips Square


Another restaurant festival is coming to the city and this time, we’re celebrating Asian local businesses and cuisine.

AsialiciousTO is running for two weeks this September and over 100 restaurants are participating.

It’s a city-wide event where restaurants introduce special menus with set price points starting at $10.

The participating venues include “restaurants, fast food, bubble tea, cafes, bakeries, and food courts of different Asian cuisines in Toronto,” according to the event’s website.

The event will wrap up with an Asialicious Carnival in Scarborough’s Woodside Square from September 15th to 17th.

When: September 16th to October 1st, 2023
Where: See participating venues

Toronto Vegandale Festival

From LA to NYC to Dallas to Chicago to Toronto, it’s a festival of all things vegan!

Vegandale will bring over 120 vendors showcasing plant-based delights from around the globe, with free samples, live music, and art showcases galore.

It’s almost the end of festival season here in our city, so whether you’re vegan or not, this is an event worth hitting up.

When: September 23rd, 2023
Where: Polson Pier & Cabana Pool Bar


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Arts, Culture & Entertainment

ROM After Dark: Being and Belonging

The ROM’s monthly after-dark party will run this September and this event’s theme is all about “being and belonging.”

Get ready for a night full of thrilling entertainment, live music, food and drinks, special activations, and of course, museum access!

When: September 22nd, 2023
Where: The Royal Ontario Museum

Toronto International Film Festival (TIFF) 2023

This September, award-winning actors and filmmakers will descend on our city for one of the most highly-anticipated film festivals of the year — the Toronto International Film Festival.

The 11-day festival is known as the world’s largest public film festival and is attended by Hollywood’s top talent every year.

Plus, TIFF’s annual Festival Street will occupy a large stretch of King Street outside of the TIFF Bell Lightbox theatre, from Peter Street to University Avenue.

Get ready for celebrity sightings and red-carpet glamour as this year’s most buzzworthy new films make their debut.

When: September 7th to 17th, 2023
Where: See the full schedule here

Just For Laughs Toronto

Toronto will be a barrel of laughs this September as world-renowned comics bring the funny at 15 stages across the city.

Fans of The Office will get to enjoy an in-person show by Angela and Pam, along with other major headliners like Andrew Schulz, Leslie Jones, and Marlon Wayans.

Plus, the free JFL street fest is returning from September 22nd to 24th outside of Berczy Park, with DJs, bands, local and sets by international comedians.

When: September 21st to 30th, 2023
Where: See all performances

Toronto International Festival of Authors

Writers, readers, and literature lovers — TIFA is back!

The Toronto International Festival of Authors is a renowned literary event “where imagination takes flight.”

Attend talks, workshops, readings, and discussions with world-famous authors, enjoy performances and kids activities, as well as a variety of free events.

When: September 21st to October 1st, 2023
Where: See full events schedule here

Anime Toronto

One of the newest and most exciting anime conventions in Toronto is making an epic return this September.

Anime Toronto will bring fans, cosplayers, and enthusiasts together for a weekend of non-stop action!

“From exclusive screenings to special guest appearances and cosplay contests, there’s something for every anime lover,” the description says.

When: September 1st to 3rd, 2023
Where: Metro Toronto Convention Centre


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Fall & Halloween Events

Cranberry Plunge at Johnston’s Cranberry Marsh

The annual cranberry harvest begins this month and to us, that only means one thing — the Ontario cranberry plunge, of course!

Johnston’s Cranberry Marsh is a sprawling 27-acre farm that produces up to 400,000 lbs of cranberries each year.

This huge harvest is something you have to see to believe, and you can get the best view possible by strapping on some waders and plunging right in.

When: Starting on September 23rd, 2023
Where: Muskoka Lakes Farm & Winery, 1074 Cranberry Rd, Bala

Halloween Haunt at Canada’s Wonderland

Spooky season is starting early at Canada’s Wonderland!

Starting on September 22nd, the park will transform into a haunted “scream park filled with Halloween attractions that offer unforgettable thrills and unspeakable horror,’ the description says.

Run from zombies, brave the haunted houses, and have a freakishly good time with your favourite skeleton crew.

And of course, enjoy some thrilling nighttime rollercoaster rides!

When: September 22nd to October 29th, 2023 (select nights)
Where: Canada’s Wonderland

Pumpkins After Dark

Canada’s award-winning outdoor Halloween event is returning to Milton!

“Featuring over 6,000+ hand-carved pumpkins, this one-of-a-kind walk-through experience is the must-see event of the fall season,” the description says.

Wander through the illuminated tunnel as thousands of unique glowing jack-o-lanterns light your path.

There will also be many new pumpkin sculptures and installations, as well as live carving demonstrations and delicious treats.

When: September 23rd to October 31st, 2023
Where: 8560 Tremaine Rd, Milton