Images of Things to do in Toronto in May

Things To Do in Toronto in May

Published: May 8, 2023

May is one of the best months to visit Toronto with sunny days and milder temperatures. The month means a return of outdoor activities, festivals, and events that will appeal to Toronto visitors – and residents – of all ages.

If you’re planning a trip to Toronto in May, UP Express is ready to welcome you on board with reliable service and affordable fares from Toronto’s Pearson Airport to downtown Toronto’s UP Express Union Station, seven days a week. Just a 25-minute ride to the bustling heart of Toronto from the airport, you’ll be ready to explore all the city has to offer this spring.

See the First-Ever WNBA Canada Game

Images of Things to do in Toronto in May

The WNBA is coming to Canada for the first time on May 13th! The WNBA Canada Game presented by Tangerine will feature the Chicago Sky and Minnesota Lynx playing a pre-season game right here in Toronto at Scotiabank Arena, adjacent to UP Express Union Station. Whether you are attending the game in-person, tuning in to the broadcast on Sportsnet and TSN, watching at the new downtown NBA Courtside Restaurant, or supporting Canadian female entrepreneurs through the new retail platform WNBA Goods presented by Mastercard, you can be a part of basketball history!

Victoria Day Long Weekend Celebrations

Images of Things to do in Toronto in May

Victoria Day is a federal Canada-wide holiday celebrated on the last Monday of May, preceding May 25. Officially, the day was first held in honour of Queen Victoria’s birthday. Unofficially, it serves as the kick off to the summer season across Canada.

The real highlight of any Victoria Day celebration in Toronto is the city’s official fireworks display at Ashbridges Bay Park in the east end. Bring a blanket and enjoy the approximately 15-minute show with thousands of spectators of all ages.

Leave the car behind on the long weekend! Avoid parking hassles and simply take UP Express to Union Station before continuing your journey eastward via TTC.

Take A Trip To The Islands

The Toronto Islands make for a great spring day trip for families, couples, friends and nature lovers. You’ll not only find the best view of Toronto’s iconic skyline from Toronto Island Park, but plenty of walking trails, bike paths, playgrounds, and more than 20 picnic spots with barbeque pits for day use.

Geared towards younger children, Centre Island’s Centreville Amusement Park has over 30 attractions – from the mild to the wild! Plus, Centre Island staple the Far Enough Farm has been welcoming visitors to its petting farm filled with over 40 species of farmyard animals and birds since 1959. Remember: kids under 12 always travel for free on UP Express! Families can also take advantage of our discounted family fare while teens and post-secondary students get 40% off standard adult fare with PRESTO.

Kick Off Patio Season

Images of Things to do in Toronto in May

You’re likely to see Torontonians enjoying (or shivering) on a patio as soon as the temperature creeps about 12 degrees Celsius on a sunny day, but patio season kicks off in earnest around the city in May. No matter your vibe or beverage of choice, experiencing a patio in Toronto is almost a rite of passage for visitors. Enjoy brunch on one of the city’s luxury rooftop patios like the Drake Sky Yard, grab a coffee and a slice of pie on the patio at Wanda’s Pie in the Sky in Kensington Market after a day of exploring, or settle back in the shadow of the CN Tower at the city’s largest open-air patio at RendezViews, a 15-minute walk of UP Express Union Station. Be sure to check out some of Toronto’s great craft breweries that are ready to welcome you to their patios for a pint in the sun.

Visit A Garden

Toronto is a city in bloom in May. Cherry blossom viewing is a popular spring pastime in the city with High Park among the top places to see the pale pink flowers in bloom. Once you’ve taken in Toronto’s tulips, daffodils, and hyacinths at St. James Park, seek out some innovative contemporary art in the Toronto Sculpture Garden across the street. For over 40 years, this outdoor space has showcased site-specific exhibitions by a variety of artists. Until August 31, 2023, Jamaican-born Toronto sculptor Frantz Brent-Harris’ Afrophilia is on display. The work is inspired by the generation of young Black people who are driving a shift in self- perception and changing our global consciousness of Blackness to appreciate its immense value, diversity, and beauty, according to the artist.

Meanwhile, you can catch dazzling floral pop-ups May 10 to 14 as Fleurs de Villes returns to Toronto’s Yorkville neighbourhood. Free to the public, “Voyage” is this year’s theme and will feature jaw-dropping floral displays inspired by iconic global destinations.

Cheer On The Home Team

Images of Things to do in Toronto in May

Join the locals in cheering on the home team this May! The Toronto Blue Jays play a series of home games at the newly-renovated Rogers Centre, an easy walk from UP Express Union Station via SkyWalk. If you’re lucky, the baseball stadium’s iconic dome will be open giving you a spectacular view of the CN Tower. If soccer is more your thing, see the boys in red dominate the field at a Toronto FC game at BMO Field in Exhibition Stadium, one short TTC streetcar ride from Union Station. Remember, as a PRESTO card holder, you can save up to 20% off ticket price to Toronto FC home matches at BMO Field during the 2023 season!

See A Play

From big Broadway extravaganzas like Hamilton and Rock of Ages to intimate productions from Crow’s Theatre, Young Peoples’ Theatre, and SoulPepper, Toronto’s arts scene offers something for everyone this spring. The city is home to several iconic theatre venues including the over 100-year-old Ed Mirvish Theatre where Harry Potter and the Cursed Child continues to delight audiences throughout May. PRESTO cardholders can save on select shows, including.

Take A Self-Guided Tour Of Public Art

Images of Things to do in Toronto in May

Photo Courtesy: Dundas West Open Air Museum

Head out on foot to explore the Dundas West neighbourhood with the artist-driven Dundas West Open Air Museum. Only a few blocks from UP Express Bloor Station, visitors can enjoy a self-guided circuit of public street art murals in the heart of Toronto’s Little Portugal located along Dundas Street West between Shaw Avenue to Lansdowne Avenue. Cap off a neighbourhood tour by checking out one of Toronto’s must-visit craft breweries located near the start and end of the Dundas West Open Air Museum route.

When it comes to hunting the perfect Instagram backdrop, look no further than Graffiti Alley. No alleyway in the city is snapped more than the Rush Alley laneway which runs parallel to Queen Street West between Spadina Avenue and Augusta Avenue, a 25-minute walk from UP Express Union Station. If there is a must-visit spot for street art in downtown Toronto, Graffiti Alley is it.

If you have a long layover in Toronto of 4 hours or more, taking a self-guided tour of the city’s public art is the perfect way to pass the time. UP Express offers the Long Layover ticket allowing guests with long flight layovers of up to 7 hours to purchase this return ticket at a reduced fare from UP Express Pearson Airport.

Explore Doors Open Toronto

Every May the city of Toronto invites the public to explore the city’s iconic buildings and sites – for free! Featuring locations of cultural, historical and architectural significance rarely open to visitors or typically require an admission fee, Doors Open is the largest event of its kind in Canada, attracting more than 200 million visits to over 700 unique locations since its inception in 2000. This year, Doors Open will be held May 27 and 28 with a list of all participating location available closer to the date.

Have Fun In The Water

Images of Things to do in Toronto in May

With the city warming up, late May brings a return to water activities. Canoe and kayak rentals and tours in Lake Ontario and around the Toronto Islands begin at the end of May, weather permitting. For something truly different, take in a magic show, music or comedy from the comfort of a canoe in the Humber River with Toronto Adventures. Be sure to check Toronto Adventures’ website for a complete schedule of live event experiences in May.

Watch A Movie

Cinephiles have endless options for movie-going in May. The year-round home of the Toronto International Film Festival, TIFF Bell Lightbox is the place to see new releases from around the world as well as retrospectives, talks, and special releases. Cinema lovers can take in a screening at one of Toronto’s beloved independent theatres for fan-favourite screenings of classics and not-so-classic flicks at the Revue Cinema in Roncesvalles Village, blocks from UP Express Bloor Station, and at the nearby Paradise Theatre on Bloor Street West. At the end of May, the annual Inside Out 2SLGBTQ+ film festival is the largest of its kind in Canada, showcasing films made by and about 2SLGBTQ+ people of all ages, races, and abilities from around the world.

No matter what time of year you plan on visiting Toronto, UP Express is always the most convenient and affordable way to travel between Toronto Pearson Airport and downtown Toronto’s UP Express Union Station in just 25-minutes. With service running every 15 minutes and complimentary Wi-Fi in stations and on board, power outlets, seat trays, roomy luggage racks, and overhead storage on every train, you can relax knowing your trip is on track.

Recent News

Toronto on a Budget: 5 Free Things to do in Toronto this Summer

UP Express has got you covered with the best FREE things to do in Toronto this summer.

Learn more
Your 2024 Guide to Toronto Pride

Pride Toronto is back, and we’re gearing up for another eventful celebration!

Learn more
Cheer on Your Team During the Cricket World Cup with UP Express

The 2024 ICC Men’s T20 World Cricket Cup is bringing cricket's excitement to the world.

Learn more
The Best Places to Explore in Toronto with Friends

We have you covered with some of the best options to explore when in Toronto with your pals.

Learn more
Explore Toronto with the UP Express Long Layover Return Ticket

Explore the city on your layover and get discounts on top attractions with the Long Layover ticket.

Learn more