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Cool Things to Do in Toronto in May

May in Toronto brings the start of night market season, the monthly flower festival, an opportunity to enter the city’s secret spaces, and the first long weekend holiday of spring.

If you’re looking for cool arts and cultural events in Toronto in May, or free things to do in Toronto in May, here are my top recommends.

Contact Photography Festival (April 28 May 31) FREE

More than 180 exhibitions and outdoor installations of photography and other “lens-based” artworks are put up around the city at this annual festival. Programming also includes talks and workshops. But if you can’t make it to a gallery just look up as you walk around the city for some of the bold Contact billboards.

Jane’s Walk Festival (May 5-7) FREE

Journalist Jane Jacobs was a beloved activist for great cities that work for the people. In her honour, Torontonians volunteer to give “Jane’s Walks” at this annual festival. It’s an opportunity to see a neighbourhood, or explore an idea, with passionate local experts. See the city in a whole new way on a guided Jane’s Walk like “Past, Present and Future of Toronto’s Waterfront,” “Coffee Culture in Trinity Bellwoods” or “Yonge Street’s Amazing Music And Pop Culture History.”

Dalhia flowers for sale in Toronto
Photo by Yusuf Baydal via Unsplash

Toronto Flower Market (May 13) FREE

Pass by West Queen West on this day and you’ll see a lot of smiling people carrying flower bouquets. They’re coming from the Toronto Flower Market at Queen and Shaw. This is the place to get beautiful Ontario-grown flowers and plants in season and talk to growers and florists. It’s kind of amazing it took so long for Toronto to get an open-air flower market but it’s now a popular monthly event in the summer. From 10am to 3pm but for best selection, go early and buy yourself something pretty. 1001 Queen Street West.

Stackt Market is a popular free thing to do in Toronto
Stackt market photo by Collision Conference via Flickr

Asian Night Market at Stackt (May 20) FREE

Stackt is an indoor/outdoor market of 120 shipping containers turned into small retail shops, event spaces and a brewery. It’s popular for casual dates and discovering local artisans, especially during their special night market events. The first one of the season is an Asian Night Market, with more than 40 food vendors, electronic music and dance performers. 4pm to 10pm. 28 Bathurst Street.

Fireworks in Toronto in May on Victoria Day
Fireworks above Canada’s Wonderland photo by designecologist via Unsplash

Victoria Day Fireworks (May 21) FREE

If you’re visiting Toronto you might hear talk of the “May 2-4 Weekend.” This is about Victoria Day, which honours Queen Victoria’s Birthday (May 24) but is also a nod to a case of 24 beers, which are often consumed on said day. The actual holiday takes place on the Monday before May 25 each year (May 22 in 2023). But you’ll find fireworks popping off around the city all weekend.

There are unofficial fireworks in most local parks, and some of the biggest parks like Trinity Bellwoods, or along the shore of Lake Ontario near Trillium Park. People just bring their own and let ‘em rip.

For much bigger bangs, there are two major Victoria Day fireworks in Toronto, both on the Sunday night, May 21.

Ashbridge’s Bay in the East End near Woodbine Beach hosts the official City of Toronto show, rain or shine. Parking nearby is crazy busy, FYI. But you can see them from pretty far away. Starts at 9:45pm lasts for about 15 minutes.

Canada’s Wonderland puts on a show with music at 10pm after the amusement park closes.

Bentway Summer Season Opens (May 24)

It’s strange to tell people to go hang out under the freeway for fun. But the Bentway has done a great job of repurposing this concrete space near Fort York with its free arts programming. The summer season opens May 24 with Beyond Concrete a collection of artworks, performances, parties, and conversations, including a choreographed handstand performance by Brazil’s Clarice Lima. That’s all free. There’s also an opening Opening Night Party on Friday, May 26, 7pm to 11pm. Tickets are $23. 250 Fort York Blvd

Also watch for the return of the Bentway’s popular Communal Table dinners, and public roller skating, details TBD.

Anime North cosplayers in Toronto
Cosplayers at Anime North, photo by Xander Ashburn via Flickr

Anime North (May 26-28)

The place to be for lovers of anime, manga, Jpop and other pop culture from Japan. Like Comic-con but specific to this community, you’ve got vendors, panels and autograph booths. And lots and lots of cosplay, with costume contests and dance parties. If you’re travelling on the subway this weekend you’re sure to spot this fandom in full regalia. Passes are $50/day or $75 for the weekend. Toronto Congress centre, Delta hotel Airport and Sheraton Toronto Airport Hotel, with free shuttles running between.  650 Dixon Rd, Etobicoke.

Lower Bay Station in Toronto
The underground Lower Bay Station, photo by Enoch Leung via Flickr.

Doors Open (May 27-28) FREE

Did you know there’s an abandoned subway station below Bay Station, called Lower Bay Station? Unless you work in a film production shooting down there, you can only access it on special events like Doors Open—which lets the public in to otherwise private spaces. For two days each May, people line up to enter historic mansions, private art galleries, and infrastructure like the R.C. Harris Water Treatment Plant. It’s kind of like club-hopping, without the hangover.

Got a favourite festival in Toronto in May that I’ve missed? Let me know in the comments below!

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