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Toronto
June 19th – Give Me Liberty 2025
Liberty Village BIA hosts its 19th Annual Street Party, celebrating all things Liberty Village. Guests can expect a fun evening of great food, live music, vendors, and a wide variety of activities that showcase the amazing businesses in Liberty Village.
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Where: Lamport Stadium Parking, 75 Fraser Avenue, Toronto
When: June 19th, 4:00 pm – 11:00 pm
Admission: Free.
(Street Party)
June 20th – Totes Prideful
Totes Prideful celebrates an evening of community, culture, and creativity with a tote bag painting workshop at the Kimpton Saint George! Express yourself, enjoy refreshments from Sapsucker, and indulge in sweet treats from queer-owned businesses to celebrate Pride 2025.
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Where: Kimpton Saint George – 280 Bloor St W, Toronto
When: June 20th, 5:00 pm – 7:00 pm
Admission: Free. Reserve your spot here
( Tote Bag Painting Experience)
June 20th to 22nd – Fairbank Summerfest 2025
Hosted by the Fairbank BIA, Fairbank Summerfest is a 3-day community festival featuring food, rides, and entertainment along long Eglinton Avenue West, West of Dufferin.
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Where: Eglinton Avenue West, West of Dufferin
When: June 20th to 22nd
Admission: Free.
(Community Festival)
June 20th to 29th – Toronto Jazz Festival
Toronto Jazz Festival is a ten-day celebration and showcase of Jazz music in Toronto.
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Where: Various Locations in Toronto
When: June 20th to 29th,
Admission: Priced and Ticketed shows.
(Jazz Festival)
June 21st – Solonda presents Taraka w/ Gordo
On Saturday, June 21, GORDO brings TARAKA to Toronto for the first time! Solonda’s most anticipated show of the summer. Taking over YZD Hangar 5, a decommissioned aircraft hangar, for a day into night experience of powerful music, striking visuals, and unforgettable energy.
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Where: YZD | Hangar 5, 10 Hanover Road, North York
When: June 21st, 3:00 pm
Admission: Priced. Tickets start at $50. Grab your tickets here
(Summer Party)
June 21st – Runway TO
RunwayTO is one of Toronto’s most anticipated summer fashion events, spotlighting the city’s boldest emerging designers and creative visionaries, providing an unforgettable evening of glamour, creativity, and cutting-edge design.
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Where: The Parkdale Hall, Toronto
When: June 21st, 5:30 pm – 10:30 pm
Admission: Priced. Tickets start at $44. Grab your tickets here
(Fashion Show)
June 21st – Local Mrkt and Village of Islington
Local Mrkt and the Village of Islington partner to host a small business market in Islington featuring over 30 small business vendors, food, live music, free kids face painting, free arts activities by Arts Etobicoke and Mabelle Arts, PWYC poetry booth and more.
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Where: 5055 Dundas St West, between Islington and Kipling.
When: June 21st, 11:00 am – 4:00 pm
Admission: Free
(Small Business Market)
June 21st – The Roots in Concert
American Legendary Hip-hop band The Roots performs at the REBEL this June
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Where: REBEL, Toronto
When: June 21st, 5:00 pm
Admission: Priced. Tickets start at $113. Grab your tickets here
(Concert)
June 21st – Na-Me-Res Pow Wow
Na-Me-Res Pow Wow, the annual community festival celebrating Canada’s National Indigenous Peoples Day, returns on Saturday, June 21st from 12:00 pm to 5:00 pm at the Fort York National Historic Site.
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This free-to-attend, family-friendly event will feature traditional dancing, drumming, and performances that reflect the richness and unique offerings of Indigenous culture in Toronto.
Where: Fort York, 250 Fort York Blvd. Toronto
When: June 21st, 12:00 pm
Admission: Free
(Indigenous Cultural Festival)
June 21st and 22nd – Rosedale Art Fair
Hosted by the Rosedale Main Street Business Improvement Area (BIA), the Rosedale Art Fair is an art showcase featuring over 80 artists, providing an opportunity to purchase original works in one of Toronto’s most prestigious neighborhoods—home to both acclaimed and emerging Canadian talent
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Where: Ramsden Park 1020 Yonge Street and LCBO Summerhill 10 Scrivener Square.
When: June 21st and 22nd, 11:00 am – 6:00 pm
Admission: Free
(Art Fair)
Outside Toronto
June 18th to 25th – Oakville Festival of Film & Arts
The 2025 Oakville Film Festival marks 12 incredible years of celebrating the best films from Oakville and surrounding communities, Canada, and across the globe! Running from June 18th to 25th, this year’s festival is bigger than ever, featuring a record-breaking 105 feature films, documentaries, and shorts.
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Where: Various Locations in the GTA
When: June 18th to 25th,
Admission: Priced. Grab your tickets here.
(Film Festival)
June 19th to 22nd – Oakville Family Ribfest
Oakville Family Ribfest returns to the Sheridan College even bigger for this year. There will be more ribs, more music, more things to see and do, more fun for the kids, more sweet treats, and more enjoyment with friends and family all weekend long.
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Where: Sheridan College, 1430 Trafalgar Rd, Oakville
When: June 19th to 22nd,
Admission: Priced. Grab your tickets here.
(Film Festival)
June 20th – Minecraft Experience: Villager Rescue
For the first time in Canada, people will have the opportunity to journey into the Overworld for an in-person, interactive Minecraft experience when Minecraft Experience: Villager Rescue debuts at Square One in Mississauga on June 20th, 2025, for a limited time.
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Where: 199 Rathburn Road West, Mississauga
When: Various Locations in the GTA
Admission: Priced. Grab your tickets here.
(Film Festival)
June 20th and 21st – Markham Village Music Festival
Experience Canadian music at its finest as you stroll up and down Main Street Markham at the Markham Village Music Festival. There will be food, a vendor market to browse, auto classics, kids’ zones, fun activities, and more.
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Where: 32 Robinson Street, Markham
When: June 20th and 21st
Admission: Free
(Music Festival)
June 20th and 21st – Stuffed Food Festival
The Stuffed Food Festival is your one-stop celebration of everything wrapped, packed, filled, and flavor-loaded. From cheesy-stuffed burgers and jam-packed dumplings to decadent éclairs and molten lava cakes, this is the ultimate destination for food lovers who believe more is more in the Vaughan Area. Guests should expect live cooking demos, local chef competitions, stuffed-themed food trucks, and unexpected culinary mashups (stuffed pizza tacos, anyone?).
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Where: Assembly Park, Vaughan
When: June 20th and 21st
Admission: Free
(Food Festival)
June 21st and 22nd – York Pride Festival 2025
York Pride is a celebration of all things Pride in the York Region, featuring parades and dedicated zones for families, youth, adults (19+), and seniors, creating space for everyone to feel seen and included.
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Where: Riverwalk Commons
When: June 21st and 22nd,
- June 21st, 10:00 am – 10:00 pm
- June 22nd, 10:00 am – 10:00 pm
Admission: Free
(Pride Festival)