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Here is our list of fun things to do in Toronto May 2025 including concerts, festivals and more!
Featured Events
May 9th and 10th – Wine Fest Toronto 2025
Toronto’s favorite wine festival, Wine Fest Toronto, returns this Spring Season on May 9th and 10th, providing 2 days of wines, drinks, and fun at a brand new location Heritage Court at the iconic Exhibition Grounds!
Where: Heritage Court (19 Nunavut Rd, Toronto)
When: May 9th and 10th,
May 9th, 6:00 pm – 9:00pm
May 10th, 1:00 pm – 4:00 pm,
May 10th, 6:00 pm – 9:00 pm
Admission: Priced. Tickets start at $82. Grab your tickets here.
Restrictions: 19+ Event
Promo Code: Use EFOSA10 for 10% off tickets)
(Wine Festival)
Things to do in Toronto – May 2025
May 3rd – Let’s Move, Willowdale
Neighbourlink hosts its third annual Let’s Move, a Willowdale community event featuring a 4km walk, run, and 8km bike ride from the park through the Finch Hydro Corridor, followed by a BBQ featuring delicious food. There are plenty of free components, including live entertainment, a caricature artist, kids’ activities, giant bubbles, milk tea, and more!
Where: Hendon Park (50 Hendon Ave)
When: May 3rd, 10:00 am – 2:00 pm
Admission: Free. Meal Tickets require purchase starting at $10. Grab your tickets here
(Community Event)
May 3rd – Leading Ladies Conference 2025
For the second consecutive year, the Leading Ladies Conference returns to Toronto on May 3rd,2025, providing a day of insightful career conversations, networking, and a $25,000 pitch competition featuring Toronto women entrepreneurs, industry leaders, and investors.
Where: National Event Centre, 1000 Finch Ave W, North York
When: May 3rd, 10:00 am – 4:00 pm
Admission: Priced. Tickets start at $135. Grab your tickets here
(Entrepreneurship Event)
May 4th – 2025 Soundwave Summit
The Soundwave Summit is a Toronto event that brings together independent podcast creators and enthusiasts, offering insights on starting and growing a podcast and providing a platform for networking, learning, and live performances.
Where: The Orange Lounge, 567 Queen Street West, Unit #300
When: May 4th, 9:00 am – 7:00 pm
Admission: Priced. Tickets start at $65. Grab your tickets here
(Independent Podcast Summit)
May 6th to 11th – Departure Festival
Experience Musical Showcases, Art, Comedy and Tech in Toronto with the reimagined Departure Festival in Toronto
Where: Various Locations in Toronto.
When: May 6th to 11th, Select Times
Admission: Priced. Tickets start at $80. Grab your tickets here.
(ArtFestival)
May 7th to 11th – GradEx 110
Toronto’s Largest Free Art and Design Exhibition, GradEx 110, will take place at OCAD University grounds from May 7th to 11th. It will feature over 800 talented emerging artists and designers in the heart of Toronto.
The four-day art and design showcase will kick off with a free public party at 6:00 pm on opening night. The party will feature music, a food truck, a bar, and art installations.
Where: OCAD U, 100 McCaul St
When: May 7th to 11th,
- May 7th, 6:00 pm – 11:00 pm
- May 8th, 9:30 am – 8:00 pm
- May 9th, 9:30 am – 8:00 pm
- May 10th, 10:00 am – 5:00 pm
- May 11th, 10:00 am – 5:00 pm
Admission: Priced. Tickets start at $80. Grab your tickets here.
(Art and Design Exhibition)
May 8th and 9th – Sadboi
Canadian Artist, Sadboi, performs at the Drake Hotel this May
Where: The Drake Hotel
When: May 8th and 9th, 7:00 pm
Admission: Priced. Tickets start at $48. Grab your tickets here
(Concert)
May 9th and 10th – Wine Fest Toronto 2025
Toronto’s favorite wine festival, Wine Fest Toronto, returns this Spring Season on May 9th and 10th. It will provide two days of wines, drinks, and fun at a brand new location: Heritage Court at the iconic Exhibition Grounds!
Guests will get to sip, taste, and celebrate a vast selection of wines and beverages from across the globe, including selections from the world’s best wine regions, including South Africa, Chile, Italy, Argentina, New Zealand, and all over Europe, including Spain’s Rioja and Rueda wine regions and France’s iconic Rhône Valley. This event will feature the best wines from Canada’s wineries, including Niagara-on-the-Lake and the Niagara Benchlands Wineries. You can view the complete list of wine vendors here.
Where: Heritage Court (19 Nunavut Rd, Toronto)
When: May 9th and 10th,
- May 9th, 6:00 pm – 9:00 pm
- May 10th, 1:00 pm – 4:00 pm
- May 10th, 6:00 pm – 9:00 pm
Admission: Priced. Tickets start at $82. Grab your tickets here.
Restrictions: 19+ event
(Wine Festival)
May 10th – SOUL KITCHEN
One of the premiere RNB events in Toronto, SOUL KITCHEN returns in May, featuring the best R&B, neo, classic soul, new jack, and slow jams at the beautiful PENTHOUSE 17 location.
Where: PENTHOUSE 17, 17 Toronto St | 3rd Floor
When: May 10th, 10:00 pm – 3:00 am
Admission: Priced. Tickets start at $22. Grab your tickets here
(Party)
May 10th and 11th – Planted Expo Toronto 2025
Canada’s largest plant-based event, Planted Expo Toronto 2025, returns this May to celebrate all things plant-based and sustainable!
At this family-friendly event, guests will discover innovative products that benefit them, the planet, and the animals we share it with. Over 200+ plant-based, vegan, and sustainable exhibitors, brands, and services will be available for you to discover, explore, and sample.
Where: Enercare Centre, 100 Princes’ Boulevard ##1 Toronto
When: May 10th and 11th, 10:00 am – 5:00 pm
Admission: Priced. Tickets start at $24. Grab your tickets here
(Vegan Planted-based Event)
May 11th – Rema (HEIS TOUR)
Afro-beats superstar and Grammy-nominee Rema performs this month at the Scotiabank arena with songs from this latest album – HEIS
Where: Scotiabank Arena
When: May 11th, 8:00 pm
Admission: Priced. Tickets start at $59. Grab your tickets here
(Concert)
May 11th – Quavo
American rapper, Quavo performs at HISTORY this month
Where: HISTORY, Toronto
When: May 11th, 7:00 pm
Admission: Priced. Tickets start at $66. Grab your tickets here
(Concert)
May 11th – Mother’s Day Boat Cruise
Celebrate Mother’s Day in style with a special Mother’s Day Brunch Cruise aboard the Obsession III on Sunday, May 11th, featuring delicious food, sparkling mimosas, jazz music, and stunning views she’ll never forget. Boarding starts at 12:00 pm.
Where: The West Pier behind Harbourfront Centre
When: May 11th, 12:00 pm – 2:30 pm
Admission: Priced. Tickets start at $90. Grab your tickets here
(Boat Cruise)
May 14th – Second Harvest Truck Pull Challenge
The Second Harvest Truck Pull Challenge is a unique team challenge that pits teams of 10 against each other in a tournament format to pull a 20,000-pound delivery truck across Nathan Phillips Square in the fastest time, raising funds for Second Harvest’s food rescue and redistribution efforts.
Where: Nathan Phillips Square, 100 Queen St West
When: May 14th,
Admission: Free
(Community Event)
May 14th to 16th – Consensus 2025
Consensus Toronto, one of the biggest crypto events of the year, bringing together over 15,000 industry leaders, developers, and enthusiasts from across the world in Toronto.
Where: Metro Convention Centre
When: May 14th to 16th
Admission: Priced. Tickets start at $800. Grab your tickets here.
(Crypto Event)
May 15th – Art Gallery of Ontario 125 Birthday Party
The AGO turns 125 this May, and they kick off the festivities with a big birthday party after hours! Guests will sip, dance, and explore—dive into dazzling visuals and hands-on activities and journey through time in AGO collections.
Where: Art Gallery of Ontario, 317 Dundas Street West, Toronto
When: May 15th, 8:00 pm
Admission: Priced. Grab your tickets here.
(AGO Birthday Party)
May 15th – Alessia Cara Live
Canadian singer and Grammy Winner Alessia Cara performs at the Roy Thomson Hall this May
Where: Roy Thomson Hall, 60 Simcoe St, Toronto
When: May 15th, 8:00 pm
Admission: Priced. Tickets start at $55. Grab your tickets here
(Concert)
May 16th – Coco Jones: Why Not More? Tour
American singer Coco Jones performs at HISTORY this May.
Where: HISTORY, Toronto
When: May 11th, 7:00 pm
Admission: Priced. Tickets start at $51. Grab your tickets here
(Concert)
May 16th and 17th – Toronto Met Film Festival
Celebrating its 29th year, the Toronto Metropolitan Film Festival showcases the diverse, innovative works of students from The Creative School, including a special selection of Image Arts Thesis Films.
Where: The Creative School Chrysalis, 43 Gerrard St E, Toronto
When: May 16th and 17th, 6:30 pm – 9:30 pm
Admission: Priced. Tickets start at $12. Grab your tickets here.
(Student Film Festival)
May 17th and 18th – Electric Island Season Opener
The highly anticipated Electric Island returns this Spring for its season opener over 2 days in May.
Where: 250 Fort York Blvd, Toronto
When: May 17th and 18th, 2:30 pm
Admission: Priced. Tickets start at $93. Grab your tickets here.
(Music Festival)
May 16th to 18th – Halal Bites Festival
Halal Bites Festival is a vibrant three-day food, culture, and art festival at Nathan Phillips Square that celebrates diverse halal cuisine, community, and artistic expression.
Where: Nathan Phillips Square
When: May 16th to 18th,
- May 16th, 6:00 pm – 10:00 pm
- May 17th, 12:00 pm – 10:00 pm
- May 18th, 12:00 pm – 8:00 pm
Admission: Free
(Food Festival)
May 22nd – Hogtown Boulders Summer Market 2025
Clmbr Arts Mrkt is an independent climbing artist market that travels to different climbing gyms in the Greater Toronto Area featuring small and local businesses in the GTA.
Where: Hogtown Boulders, 238 Lesmill Rd, North York
When: May 22nd, 8:00 pm
Admission: Free
(Summer Market)
May 22nd – Cypress Hill: O CANADABIS 2025 Tour w/ De La Soul & The Pharcyde
American hip-hop group, Cypress Hill performs at Coca-Cola Coliseum this May.
Where: Coca-Cola Coliseum, Toronto
When: May 22nd, 8:00 pm
Admission: Priced. Tickets start at $83. Grab your tickets here
(Concert)
May 22nd – Chilliwack – GONE, GONE, GONE, Farewell to Friends Tour
Canadian Rock band Chilliwack performs in Toronto this month.
Where: Massey Hall, 178 Victoria Street, Toronto
When: May 22nd, 8:00 pm
Admission: Priced. Tickets start at $52. Grab your tickets here
(Concert)
May 22nd to 25th – Estonian Music Week 2025
Estonian Music Week is a celebration of Estonian and Estonian-Canadian artists in Toronto. Over four days, there will be fun activities, networking, and, of course, great performances.
Where: Various Locations in Toronto
When: May 22nd to 25th,
Admission: Priced. Tickets start at $115. Grab your tickets here
(Music Event and Series)
May 23rd – Billy Idol & Joan Jett and The Blackhearts – It’s a Nice Day To… Tour Again
Billy Idol performs in Toronto this May at the Budweiser Stage.
Where: Budweiser Stage, Toronto
When: May 23rd, 7:30 pm
Admission: Priced. Tickets start at $60. Grab your tickets here
(Concert)
May 23rd to 25th – Asian Heritage Cultural Festival
Asian Heritage Cultural Festival is a 3-day event celebrating Asian Heritage, culture, community, and food in Toronto.
Where: Bridlewood Mall,
When: May 23rd to 25th, 11:00 am – 11:00 pm
Admission: Free
(Cultural Festival)
May 23rd to 25th – Anime North
Anime North hosts an anime convention celebrating anime, manga, music, games, and all other forms of Japanese culture!
Where:
- Toronto Congress Centre,
- Delta Hotel Airport.
When: May 23rd to 25th,
- May 23rd, 5:00 pm – 1:00 am
- May 24th, 10:00 am – 1:00 am
- May 25th, 10:00 am – 5:00 pm
Admission: Priced. Tickets start at $45. Grab your tickets here
(Anime Convention)
May 24th – 2025 motionball Marathon of Sport Toronto
motionball, a national non-profit organization that empowers young professionals to become leaders in their communities, hosts its annual flagship event, Marathon of Sport Toronto, on May 24th at the York University Campus.
Returning for its 24th year, the Marathon of Sport Toronto brings people and communities with and without intellectual disabilities together to build lasting connections while competing in a full day of fun activities.
Where: York University (Keele Campus), 198 York Blvd, North York
When: May 24th, 7:30 pm
Admission: Priced. $50. Register here.
May 24th and 25th – Doors Open Toronto
Doors Open weekend provides the unique opportunity to explore Toronto’s architectural, historical, cultural, and socially significant buildings for free this May. With sports, music and theatre venues and more than 150 sites to discover, the city becomes an urban playground. You can view the complete list of locations here.
Where: Various locations in Toronto.
When: May 31st, 7:00 pm
Admission: Free
(Doors Open)
May 24th and 25th – TOFW Fashion Week
Toronto’s Own Fashion Week is a 2-day fashion showcase featuring Toronto’s talented fashion designers at the beautiful Toronto Reference Library. Guests will witness beautiful models strut off the runway with the latest collections from Toronto’s designers. There will be an exclusive marketplace and a chance to explore an art gallery.
Where: Toronto Reference Library, 789 Yonge Street, Toronto
When: May 24th and 25th, 7:00 pm – 12:00 am
Admission: Priced. Tickets start at $22. Grab your tickets here
(Fashion Show)
May 24th and 25th – Central Cee (Can’t Rush Greatness 2025 World Tour)
British rapper Central Cee performs at HISTORY this May as part of his Can’t Rush Greatness 2025 World Tour.
Where: HISTORY, Toronto
When: May 24th and 25th, 7:00 pm
Admission: Priced. Tickets start at $266. Grab your tickets here
(Concert)
May 26th – Shakira – Las Mujeres Ya No Lloran World Tour
International pop superstar Shakira will perform at the Scotiabank Arena this May as part of the Las Mujeres Ya No Lloran World Tour.
Where: Scotiabank Arena, 50 Bay Street, Toronto
When: May 26th, 7:30 pm
Admission: Priced. Tickets start at $389. Grab your tickets here
(Concert)
May 26th – Post Malone – The BIG ASS Stadium Tour
American country artist Post Malone performs at the Rogers Centre this May
Where: Rogers Centre, 1 Blue Jays Way, Toronto
When: May 26th, 7:30 pm
Admission: Priced. Tickets start at $298. Grab your tickets here
(Concert)
May 29th – Dixonlicious 2025
Dixonlicious 2025 is a community culinary extravaganza in support of Dixon Hall’s Food Programs! Guests will get to sample mouth-watering cuisine from diverse and creative food offerings, paired with a selection of craft beers, fine wines, and other beverages to complement every delicious bite.
Where: Daniels Spectrum, 585 Dundas St E, Toronto
When: May 22nd, 6:00 pm – 9:00 pm
Admission: Priced. Tickets start at $85. Grab your tickets here
(Culinary Community Event)
May 29th to June 1st – Fashion Art Toronto
Toronto’s biggest and longest-running fashion week celebrates its 20th year of bold fashion with four days of runway shows, art, shopping, and more!
Where: 251 Queens Quay East
When:
- May 29th, 5:00 pm – 11:00 pm
- May 30th, 6:00 pm – 11:00 pm
- May 31st, 3:00 pm – 11:00 pm
- June 1st, 3:00 pm – 11:00 pm
Admission: Priced. Tickets start at $33. Grab your tickets here
(Fashion Show)
May 30th – Tyrese
American actor and singer Tyrese performs at the Great Canadian Toronto Arena this May
Where: Great Canadian Toronto
When: May 30th, 8:00 pm
Admission: Priced. Tickets start at $67. Grab your tickets here
(Concert)
May 30th to June 1st – Prepare the Ground 2025
PREPARE THE GROUND is a community-led arts and heavy music festival taking place across multiple venues in Toronto, Ontario—the first of its kind in the city. Guests should expect great performances from talented heavy metal artists. There will also be a vendor business market in support of small businesses in Toronto.
Where: 918 Bathurst
When: May 30th, 8:00 pm
Admission: Priced. Tickets start at $90. Grab your tickets here
(Concert)
May 31st – Barry Manilow (The Last Toronto Concert)
American singer and songwriter Barry Manilow performs at the Scotiabank Arena this May.
Where: Scotiabank Arena
When: May 31st, 7:00 pm
Admission: Priced. Tickets start at $53. Grab your tickets here
(Concert)
As always, you can keep up with all the fun happenings in Toronto and the Greater Toronto Area on efosa.