Toronto’s summer festival calendar has no shortage of concerts, but On the Way Festival is setting out to offer something different.
Returning to The Bentway on August 15, the independently produced festival brings together a carefully curated lineup of music, food, wine and local culture, transforming the unique urban space beneath the Gardiner Expressway into an immersive celebration of the city’s creative spirit.
On the Way Festival began as a grassroots collaboration between two Toronto businesses, Community Wines and Standard Time. Now, On the Way has quickly become one of Toronto’s most anticipated boutique festivals, bringing together internationally recognized artists including The Dare, Ross From Friends, DJ sets from members of BADBADNOTGOOD, Patrick Holland, Doss and Young Teesh.
Beyond the music, festivalgoers can expect some of the city’s favourite independent food and beverage vendors, including Matty’s Patties, Ruru Baked, Rizzo’s, Rooms Coffee, Barbet and, of course, Community Wines. Festival vibes are curated in partnership with the venue expertise behind Geary Avenue bar and record shop Standard Time.
For Community Wines founder Blake Pearson, the festival grew naturally from years of collaboration between the two Toronto businesses.
“Community Wines and Standard Time have been throwing parties together for a few years now, and OTW is the natural evolution of that,” Pearson says. “We share the same values, the same love for Toronto and its music community, and we both felt like there was a real gap. The talent, the taste, the audience is all there, but the festival side of the city hasn’t kept up with it.”
Rather than simply assembling an impressive lineup, the organizers wanted to create an event that reflects the city’s interconnected creative communities.
“The intention has never been just to book artists individually, but to create a broader cultural atmosphere,” explains Standard Time’s Malcolm Levy. “Blending nightlife, hospitality, food, wine and culture into something that felt less like a traditional festival and more like a reflection of the overlapping creative communities shaping contemporary culture today.”
On the Way places a deliberate focus on independent businesses, highlighting the restaurants, cafés and beverage makers that help define Toronto’s cultural identity.
“That’s actually what makes Toronto’s scene great,” Pearson says. “It’s not the big obvious names and corporations, it’s the network underneath them—from the artists to the chefs, the people running rooms and pop-ups all over the city. If we’re saying OTW is a snapshot of Toronto’s culture right now, it has to include them.”
Levy agrees, adding that independent businesses are “the foundation of Toronto’s cultural identity,” and bringing them together creates an ecosystem where artists, audiences and local communities can all thrive.
That holistic approach is something attendees will experience from the moment they arrive. Levy says every detail has been thoughtfully considered, from the visual design and lighting to the hospitality and culinary offerings.
“For us, music is only one part of the experience,” he says. “Every element, from the lighting, visuals and stage design to the food, natural wine and hospitality, has been intentionally curated to create an immersive environment where people can slow down, explore and enjoy the moment. We want guests to leave remembering not just who they saw perform, but how the entire festival felt.”
Ultimately, the founders hope On the Way leaves attendees with more than memories of great performances.
“The best festivals don’t just entertain you, they remind you why you love the city,” says Pearson. “We want to keep pushing Toronto pride and putting on this incredible community we have. At the end of the day we just want people to have the best day and leave feeling inspired to keep creating in this city.”
With a thoughtfully curated lineup, a strong emphasis on independent businesses and a distinctly local point of view, On the Way Festival continues to carve out its own space in Toronto’s cultural landscape, one that celebrates not only the artists on stage, but the creative community that makes the city what it is.
For tickets click here and check out the lineup below.
*images by Melissa Matheson
Nadia Elkharadly