There is no better time to enjoy the outdoors while engaging in live entertainment than during a Toronto summer. With July coming to a close, street festivals, arts markets, and dance performances by the dock are all attractions to look forward to this week. From the grand return of OssFest to Soulpepper’s intimate showcase of first-time storytellers, here are some events worth checking out.

 

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Battle By the Water

Catch some of Toronto’s top talent in a dance face-off by the waterfront at this free event. Battle By the Water will feature a 1 vs. 1 House/Salsa fusion dance competition, where the Top 3 performers will walk away with a cash prize. In addition to watching the dancers make the dockside their dancefloor, attendees are also expected to feel the groove with DJ Sisco’s electric mix of Salsa and House music. More info.

When: July 22

Where: 319 Queens Quay West

StreetFest

This street festival is turning the iconic stretch between Woodbine and Beech Ave. into a live music destination. With three unforgettable nights powered by acts playing anything from jazz to blues, StreetFest will also offer gourmet snacks and sweet delights from the city’s best restaurants and food trucks. Grab a bite, watch the bands and musicians taking the stage, and shop handmade goods from local artisans and vendors. More info.

When: July 24-26

Where: Queen St. E – between Woodbine and Beech Ave.

 

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OssFest 2025

This Saturday marks the return of the beloved OssFest, a summer street festival that combines wellness and leisure. In the morning, expect a focus on health and in the afternoon, expect a vibrant party that will run until the evening. Purchase goods from the market on site, explore the festival’s 25 extended patios, and take in music and entertainment for an entire day. More info.

When: July 26

Where: Ossington Strip – between Dundas St W and Queen St W

Freshly Hatched: True Stories From First Time Storytellers

Soupepper and Replay Storytelling are partnering for a special and intimate night, dedicated to first-time storytellers. After engaging in a day-long intensive training, eight participants will share their personal, workshopped pieces with a crowd in Soulpepper’s outdoor courtyard. This singular event comes as an opportunity to support emerging talent in some of their first storytelling ventures. More info.

When: July 26

Where: Soulpepper Theatre

Summer Live Music Festival

The sixth edition of Summer Live Music Festival is kicking off this Saturday at Trillium Park, featuring award-winning jazz bands, acapella groups, and world music. Bring your lawn chair or blanket and enjoy a vibrant lineup of performances across genres. There will also be food vendors on the ground, appeasing your taste buds while you listen to the sounds of summer. More info.

When: July 26

Where: Trillium Park

New Horizon: Women Speak Up Toronto Launch

To celebrate six years of Women SpeakUp Canada, the New Horizon Toronto Launch will bring the community together for workshops, mixers, and panel discussions that will leave you inspired. Toronto women are bound to experience a day of connection and empowerment, in a place where attendees will learn how to tell their stories with confidence. Engage with like-minded people, listen to tips and tricks from notable guest speakers, and take your chance on winning prizes. More info.

When: July 26

Where: Gallery TPW

Dreamscapes Screening: National Tour Kick-Off

Enjoy an evening dedicated to experimental film, live performance, and a post-show artist talk-back. Dreamscapes is a genre-blurring short film that explores mental health and the complex journey to healing through the lens of Amelia Rose Griffin. Offering a personal perspective on Disability, Dreamscapes focuses on Griffin’s experience navigating multiple realities to life through vivid dream imagery. More info.

When: July 26

Where: Tangled Art + Disability

Guild Alive with Culture Arts Festival

This family-friendly, weekend-long festival features over 100+ local and regional artists, performers, and food vendors. You’ll be able to explore art and heritage exhibits, stroll through the arts market, enjoy live entertainment, and participate in workshops catered to all ages. The Guild Alive with Culture Arts Festival is a must-attend summer event, highlighting Scarborough’s cultural spirit and small businesses. More info.

When: July 26-27

Where: Guild Park and Gardens

 

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Anne of Green Gables – 40th Anniversary Screening

A Canadian epic is turning 40, and Hot Docs is hosting a special screening to celebrate it. Based on the classic novel by Lucy Maud Montgomery, Anne of Green Gables is a charming tale of an orphan girl who is mistakenly sent to the home of elderly siblings, who were instead looking to adopt a boy to help them with the farm.  Yet, it is with her imagination and wit that Anne wins the Cuthberts over, all the while she is going through her own coming-of-age journey. More info.

When: July 27

Where: Hot Docs Ted Rogers Cinema

 

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Indigenous Sounds Now

As part of the SummerSeries in Trillium Park at Ontario Place, Indigenous Sounds Now spotlights Indigenous artists and voices from the Anishinaabe, Mohawk and Cree Nations. The lineup for this event is filled with Indigenous musicians, some of which are JUNO award nominees. Listen and dance to Indigenous music that spans genres, with artists playing anything from pop to rock while bringing the crowd in. More info.

When: July 27

Where: Ontario Place