Must-see May events in Toronto

May 1, 2017

By Jenn Reid

Happy May! We’re transitioning from spring into summer (finally!) and the city is ready for that warm weather! Outdoor events, festivals and markets are popping up all month long, and you’ll want to soak up the sun at all of them. Don’t forget the cool concerts, delicious foodie festivals and all the Victoria Day long weekend celebrations. Check out the must-see events happening this May in Toronto. [Photo credit: Courtesy of Electric Island]

Must-see May events in Toronto

Contact Photography Festival

Spring in Toronto means the return of the Contact Photography festival, with outdoor installations and exhibits on display across the city. This year’s theme is all about Canada, since it’s our 150th birthday and all. You can catch exhibits at the Ryerson Image Centre, Fort York, the TIFF Bell Lightbox and more.

  •    When: April 28 to May 31
  •     Where: Various locations across Toronto
  •     Price: Free
  •     More Event Info

Brewers Plate

There are plenty of food festivals in Toronto, but only one combines food, beer and rock music. Brewers Plate pairs local brews (like Steam Whistle or Great Lakes Brewery) with local chefs (like the masterminds behind Mangia & Bevi or Heirloom Toronto) for perfect meal and drink pairings, with music from Billy Talent’s Ian D’sa. Dress code? Vintage rock tees, of course. The event is a fundraiser for War Child Canada, so bring cash for a raffle - prizes TBA.

Jane’s Walk

Nothing better celebrates activist and author Jane Jacobs’ legacy than Jane’s Walks. Jacobs fought for better urban planning and making cities livable, and every year that idea lives on in a series of citizen-led walks around the city. You can explore every inch of Toronto, whether it’s learning the history of your own neighbourhood, checking out the architecture of a new part of town, or learning about the environment or conservation in one of our many parks.

  •    When: May 5 to 7
  •    Where: Various locations across Toronto
  •     Price: Free
  •     More Event Info

Cinco de Mayo

If you can’t get to Mexico for Cinco de Mayo, the next best thing is having Mexico come to you. Chef Donnie Masterson, of The Restaurant in San Miguel de Allende, Mexico, serves up delicious Mexican eats at the Drake One Fifty for one night only. You can choose to eat a-la carte or get a prix-fixe meal for $75. Tequila cocktail pairings are available and live Latin music plays all night.

Leslieville Food & Drink Festival

Never let anyone tell you the east end doesn’t have fun! Leslieville is celebrating all east end businesses at this food fest, where you can sample the best food, beer and wine in the neighbourhood. There’s also a chef demonstration by Toronto Food Tours’ Chef Scott, a food and wine pairing seminar, an artisanal food market and more. Tasting tokens and a souvenir glass are included with a ticket purchase.

Toronto Flower Market

All summer long you can shop fresh, local flowers in downtown Toronto. The Toronto Flower Market opens this month and happens one Saturday a month for the rest of the season. All the vendors are local Ontario growers, and you can pick up bouquets and potted plants, plus learn tips on how to grow your own garden.

Toronto Comic Arts Fest

Comicon and FanExpo are all about celebrity panels and major publishing houses like Marvel and DC, but if you’re into indie presses, meeting artists and creators or picking up all kinds of new comics, you should check out the Toronto Comic Arts Fest. Join panels, attend signings and workshops from local and international artists, and shop from hundreds of different vendors.

Mother’s Day Brunch

Your mom deserves something nice for Mother’s Day, no? What about brunch in a castle? Casa Loma’s annual brunch is an extravagant affair, with options like a seafood bar, New York striploin, charcuterie, crepes and more. Admission to Casa Loma is included, so you can browse the castle and gardens after your meal.

Toronto Festival of Beer: Spring Sessions

Toronto Festival of Beer is one of the biggest beer fests of the summer, but you don’t have to wait for the season to change! The Spring Sessions happen over the May 24 weekend with major “weekend at the cottage” vibes. Enjoy some beer (obviously), BBQ and acoustic, campfire-style performances from Elliot Brood and the Trews. Sample tokens are included with tickets, and more can be purchased on-site.

Electric Island

You can spend the May long weekend on Toronto Island at a concert! Actually, you can spend every long weekend on Toronto Island at concert! Electric Island happens every long weekend in the summer, with a line-up of different EDM artists at each show. The Victoria Day concert features Ben Klock, Joris Voorn Eats Everything, Leon Vynehall and more.

Inside Out Film Festival

The Inside Out Film Festival brings the best LGBT cinema from around the world to Toronto. This year’s films are still to be announced, but in previous years the fest has screened movies like Closet Monster, Tom at the Farm, Weekend and The Normal Heart.

The Weeknd

It seems like every major act rolls into town during the summer. It’s a jam-packed concert slate but if, for whatever reason, you can only catch one, the biggest party will likely be at the ACC for The Weeknd. The Scarborough native has blown up over the past few years (a far cry from his secret Toronto shows back in the House of Balloons days) and the massive crowds will surely give him a warm welcome home.

Doors Open Toronto

Doors Open is the perfect (and sometimes only!) chance to get a peek inside some major Toronto buildings. More than 100 buildings with cultural significance, an interesting history or just cool architectural features open their doors to the public. Some participating buildings will be ones that have never been open to the public before, and others will have cool perks or things to do after the tour.

  • When: May 27 to 28
  • Where: Various venues across Toronto
  • Price: Free
  • More Event Info

Pedestrian Sundays

Kensington Market is a lively part of the city at any time, but Pedestrian Sundays are truly special events. The whole neighbourhood closes its streets to cars so pedestrians can move freely through the area, with street performers, musicians, artists and more. It’s a great excuse to shop and eat local!

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