A wonderful weekend is in store for us, friends. The sun is shining and the city is coming alive, which means there is a whole world of things to do in Toronto this weekend.

And guess what? We’ve rounded up the very best of them right here.

Let’s not waste another moment and dive right into the best things to do in Toronto this weekend. And most importantly, have some fun!

Pedestrian Sunday at Kensington Market

The Sunday street parties we know and love are officially coming back to Kensington Market.

Pedestrian Sundays return for the season this Sunday, May 28th, and will continue well into the fall.

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

When: May 28th, 2023
Where: Kensington Market

The Word on the Street Festival

Canada’s largest free outdoor book and magazine festival is returning to Toronto this weekend.

Join this annual celebration of Canadian literature and writers and browse the vibrant marketplace of the best books and magazines out there.

Whether you’re a bookworm or a casual reader, this free community street festival is not one to be missed!

When: May 27th and 28th, 2023
Where: Queen’s Park

Sponsored Pick: Doors Open Toronto 2023

Get ready to unlock the treasures of our incredible city! It’s that time of year again, folks—Doors Open Toronto 2023 is back this weekend with access to 140+ of the city’s most architecturally & culturally significant buildings. Explore hidden gems, discover secret spots & indulge in the rich history of Toronto—all for FREE!

When: Saturday, May 27 and Sunday, May 28, 2023
Where: click here for our top 10 places to visit & the full list of 140+ sites.
Cost: FREE!

Fiesta De Mayo

This weekend, you can look forward to a festival that celebrates the culture and diversity of our great city.

Fiesta de Mayo will feature tribal drums, colourful street dancing, and a wide variety of delicious food and drinks. A dream combination, if you ask us!

When: May 26th to 28th, 2023
Where: Street Eats Market, 500 Progress Avenue, Scarborough

Sponsored Pick: Little Canada presents: East Coast of Canada Launch Party

@littlecanada is excited to bring the East Coast of Canada to Toronto through a miniature word. And they’re having a party to celebrate! 

@littlecanada is excited to launch their newest Destination, Little East Coast! And to celebrate, they’re hosting a party!

On June 2nd, visit Little Canada at The Tenor in Toronto and dance the night to live East Coast entertainment! Enjoy Atlantic inspired little bites and treats while exploring the newly opened, Little East Coast. Tickets cost $99.

The Bentway Opening Weekend

Toronto’s beloved outdoor hub below the Gardiner Expressway is reopening this May with a new season of programming, called Beyond Concrete.

In celebration of its opening weekend, visitors can attend free talks, tours, and workshops.

Plus, there are several installations that the public can enjoy for free throughout the season.

That includes a special live art performance on May 27th and 28th.

When: Starting on May 26th, 2023
Where: 250 Fort York Boulevard

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Party for Paws Spring Pet Fair

This annual free pet-centric party is coming back this month, and it’s pawsitively awesome.

The family-friendly and fully accessible event allows you to start your animal adoption journey, support local businesses, and meet celebrity pets all in one place.

There will be all kinds of fun things to do for your pet too, including doggie pools and tunnels, a photo booth, treats for pets, goodies, and more.

When: May 27th & 28th, 2023
Where: Trinity Bellwoods Park, Dog Bowl, 790 Queen Street West

Anime North 2023

The popular anime convention we know and love is coming back to our city this week.

This weekend-long event is a celebration of anime, manga, music, games and all other forms of Japanese Culture.

When: May 26th to 28th, 2023
Where: Toronto Congress Centre, Delta Hotel Airport & Sheraton Toronto Airport Hotel

Marathon of Sport Toronto 2023

This weekend, you can attend a dynamic sporting event for a great cause.

National not-for-profit motionball for Special Olympics is hosting its 2023 Marathon of Sport on Saturday.

The annual event will host sixty teams participating in a variety of sports, including football, giant pong, ultimate frisbee, bench ball, handball, soccer, and bocce ball, all to raise awareness for the Special Olympics movement.

When: May 27th, 2023, 9 AM to 4 PM
Where: University of Toronto Varsity Field, Varsity Arena, Goldring Centre, and the back campus fields

AGO Friday Nights

After-dark parties at the gallery are making a comeback this Friday.

This event features a and DJ , as well as curated selection of works from AGO Library and Archives.

This month’s edition is all about spotlighting new exhibitions and artists at the gallery, including Sunday School storytellers, Naudline Pierre, and Wolfgang Tillmans.

When: May 26th, 2023
Where: Art Gallery of Ontario