Since opening our doors in 2010, Side Street Surfing has been the heartbeat of Longboard Living. What started as a simple idea—bringing riders together to share our passion for longboarding—has grown into something truly special. This year alone, we hosted over 25 Side Street Surfing events, and each one reminded us why we do this.

More Than Just a Ride

Every week, we gather at our Kensington Market shop at 7pm. Staff, customers, friends, followers—everyone's welcome. The route changes each time, but the vibe stays the same. We cruise low-traffic side streets, discover hidden alleyways, parks with paths, and find those cool spots that make Toronto such an incredible city to skate.

Side Street Surfing is guiding light synonymous with who we are as a brand. It's our dedicated time each week to roll together, to develop skills, to try new boards, and to experience all the benefits that come from sharing your passion with like-minded people.

The Community We've Built

Over 15 years, we've watched friendships form, skills progress, and a true community take shape. Whether you're testing out a new deck, pushing your carving technique, or just enjoying the ride, Side Street Surfing is where it happens. It's where beginners find their confidence and experienced riders find their crew.

This is what longboarding is all about—the freedom of the ride, the energy of the group, and the shared stoke that keeps us coming back week after week.

2025 Season Highlights

Check out some of our favorite moments from this year's Side Street Surfing sessions below. Here's to many more years of rolling together!

Join us for our next Side Street Surfing session—7pm at Longboard Living, Kensington Market. All skill levels welcome.