The Best Things to Do in May in Toronto

Nathan Philips Square in Toronto

TripSavvy / Brakethrough Media

Due to remaining closures and precautions in Toronto, many of these events are canceled or postponed for 2020.

May is a particularly busy month in Toronto. It seems as if the city is finally ready to bust out of a collective post-winter rut and really get out and enjoy what Toronto has to offer. And there are lots of cool things on the go in May. From music and food fests, to art, photography and beer, there’s something for everyone happening this month. Here are the best May events in Toronto.

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Contact Photography Festival (May 1-30, 2019)


 Contact Photography Festival

May is your chance to check out the world’s largest annual photography event in the form of Scotiabank Contact Photography Festival. This year’s event marks the 23rd edition of the festival, which features a month of photo exhibits and public installations all across Toronto and the GTA. This year’s fest will bring together over 1500 artists and photographers, both local and internationally based that you can see in over 200 unique and exciting exhibitions and events.

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Canadian Music Week (May 6-12, 2019)

Music fans will want to check out Canadian Music Week, which is Canada’s biggest new music festival and also recognized as one of the premier entertainment events in North America. You can expect seven nights of live performances by hundreds of bands at more than 40 live music venues in downtown Toronto.

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Spring into Parkdale (May 11, 2019)


Pardale BIA


Parkdale’s annual spring sidewalk festival is happening early in the month and it’s a great chance to get to know a new neighbourhood if you’re not familiar with Parkdale, or rediscover what it has to offer if you haven’t been in a while. Parkdale is filled with an eclectic selection of shops, restaurants, bars and galleries and the festival makes it easy to explore them all. Plus there will be deals to be found at various stores, food samples to try, entertainment, face painting, a kids’ zone and cotton candy.

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Tastemaker Toronto (May 10-12, 2019)




Foodies take note — Tastemaker Toronto is an event you won’t want to miss. Taking place at the scenic Evergreen Brick Works, the event brings together many of Toronto’s best chefs, producers, mixologists and restaurants for a chance to eat, drink, learn and have a great time in the city.

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Doors Open (May 25-26, 2019)

The end of May once again gives Torontonians the chance to take a look inside some the city’s most historic, unique and noteworthy buildings with Doors Open. For two days get free access to 130 buildings that are either culturally, historically or socially significant to the city. Oftentimes, these are buildings the public doesn’t normally have access or at least doesn’t have this much access to. The theme of 2019’s Doors Open is "20 Something" and will celebrate the first 20 years of Doors Open Toronto while also looking towards the next 20 years.  

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Artfest Toronto (May 18-20, 2019)

The historic Distillery District will be hosting Artfest Toronto May 18 to 20 this spring (there’s also one happening August 30 to September 2), which will feature a curated selection of 80 artists from across Ontario, Quebec and beyond. The art on offer covers everything from sculpture and photography to painting and glass art. There will also be live music and an Artfest Kids pavilion just for the little ones with free art workshops.

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Woofstock (May 25-26, 2019)


Brighton Dog Photography


Have a dog? Just love to be around dogs? You’ll want to get yourself to Woofstock happening May 25 and 26 in Woodbine Park. The free event is the largest outdoor festival for dogs in North America where you can hang out with your pooch, checking out vendors selling everything from toys and snacks to dog fashion. And if you don’t have your own dog but just really, really like dogs, this is a great chance of seeing a ton of pups and maybe even getting to play with a few.

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Pedestrian Sundays in Kensington Market (starting May 26, 2019)

Put on your walking shoes and explore Toronto’s colorful Kensington Market without the noise of cars. The neighborhood goes car-free for Pedestrian Sundays beginning May 26, 2019 and continuing through until the last Sunday in October. Expect musicians, buskers, activities for all ages and delicious food.

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