Looking for ways to make the most of the last stretch of summer? Toronto is packed with festivals, outdoor performances, and community celebrations this weekend—from music and food to art, culture, and even a carnival for dogs.
Whether you’re in the mood to dance in the streets, try your hand at painting, or sample flavours from around the world, there’s something happening in every corner of the city.
Here are some of the best events to check out from Friday, Aug. 22 to Sunday, Aug. 24.
Friday, August 22
Summer in the Park
Weston’s Little Avenue Memorial Park will be buzzing with three days of free music, dance, theatre, and storytelling as Summer in the Park returns.
This year’s program spans everything from soulful R&B courtesy of Kibra, to high-energy performances by Tribal Vision Dance, circus arts from The Grand Salto Theatre, and powerful spoken word by Irmão and other Toronto voices.
Guests can also gather for a community meal and cap off the weekend with a lively party in the park. The entire festival is family-friendly, fully accessible, and designed with a relaxed environment approach—making it welcoming for everyone.
Cost is free, registration is open, and to view the performance schedule, check it out here.
Trivia & Paint Night
Put your creativity and quick thinking to the test at this mash-up of painting and trivia, hosted by Artbox Studio.
Guests will be guided through creating their artwork. The session’s feature is a “Dreamy Sunset,” but freedom painting is also welcome, with rounds of general knowledge trivia interspersed between brushstrokes.
Expect icebreakers, team play, snacks, and plenty of good vibes, with prizes for the winners.
Tickets are $45, and can be purchased here.
Arts in the Parks: The Flying Machine
Flagstaff Park in Etobicoke transforms into a stage for an outdoor circus spectacular this week from 5:30–7 p.m. from August 20 to 24.
Watch as three performers take to stilts, ropes, and hoops to tell the story of a quirky inventor and her time-travelling machine.
The show blends circus, dance, and theatre with a touch of clowning, inviting audiences of all ages to embrace imagination and play.
Before each performance, SoCirC will host free community workshops where guests can try juggling, balancing, and other circus skills—with the chance to join the show themselves.
The event is free.
Saturday, August 23
Parkdale Music Crawl
On Aug. 23, Queen St. W. from Roncesvalles Ave. to Dufferin St. (10 a.m.–2 a.m.) turns into a non-stop celebration of music, food, and community.
The Parkdale Music Crawl brings live performances to indoor and outdoor stages all day long—jazz, blues, DJs, buskers, duets, and more—stretching from morning family fun to late-night sets.
The Sidewalk Sale (10 a.m.–9 p.m.) adds even more energy, with local shops, vendors, and tasty eats spilling out onto the street. It’s an all-day neighbourhood party and one of the biggest showcases of Parkdale’s creative spirit.
Doggie Fest Summer Carnival
Toronto’s vibrant celebration for pups and their people returns on Aug. 23 at Roundhouse Park from 11 a.m.–4 p.m.
The free festival packs the day with agility courses, splash pads, a lure track, and a ball pit designed for four-legged fun, alongside live music, photo ops, and a dog-friendly patio from Steam Whistle Brewing.
More than 30 local vendors will be on site with treats, toys, and unique finds, while mini train rides and family activities round out the carnival vibe.
Admission is free.
Sankofa Day
Toronto hosts Canada’s first major public Sankofa Day on Aug. 23 at Sankofa Square (formerly Yonge and Dundas Square), from 10 a.m. to 11 p.m.
This free festival begins with a powerful opening ceremony and features Indigenous and African ancestral acknowledgements alongside youth performances.
All day long, the square will pulse with Afro-Caribbean food and music, art installations, film screenings, and live sets—including a free DJ performance by Kardinal Offishall.
Sports activations with the Raptors and HOOPQUEENS add to the energy, and the celebration wraps up with a closing party by the globally renowned MOONSHINE collective.
Find more information here.
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Sunday, August 24
Kalamansi Fest
On Aug. 24, STACKT Market (28 Bathurst St.,) hosts the first-ever Kalamansi Fest, presented by Kalamansi Collective and Barkada MRKT, from 12-6 p.m.
This free event celebrates the Filipino citrus fruit with a full day of food, vendors, and community. Expect beloved local makers, new vendors, and plenty of kalamansi-inspired eats and treats — a taste of home and culture in the heart of Toronto.
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TAIWANFest
Catch the closing day of TAIWANFest on Sunday, Aug. 24 at Harbourfront Centre from 12–6 p.m.
Art, food, and performances come together to explore identity and migration.
With exhibitions, films, and family-friendly activities rounding out the program, it’s the perfect way to experience the festival’s blend of Taiwanese and Portuguese diasporic culture before it wraps up.
Admission is free, and you can check out the program here.
Afro-Carib Fest
Dive into the sights, sounds, and flavours of African and Caribbean culture at Afro-Carib Fest all weekend long at Thomson Memorial Park from 12–9 p.m
This free, award-winning festival features drum and dance workshops, a cultural parade, live music, dance competitions, raffle draws, and a bustling vendor marketplace with food trucks and local businesses.
With family activities and a kids’ zone, it’s a full weekend of culture, community, and celebration.
For a list of events, check out our events calendar, powered by Now Playing Toronto.
To list your event, click here.
