Each year, late summer invites paddlers to gather at Scarborough’s Cherry Beach for a unique test of water and will—the Annual Cherry Beach Paddle-In. This event is more than just a casual float; it’s an immersive experience where participants navigate Lake Ontario’s currents, engage with other outdoor enthusiasts, and celebrate the city’s lakeside edges. The journey begins on the water, with a route that challenges beginners and seasoned paddlers alike by weaving through open waves and protected bays, each section daring you to keep pace with the lake's own restless rhythm.

The Paddle-In covers approximately 10 kilometers from starting points along the Scarborough Bluffs, moving toward Cherry Beach’s sandy shores. As the lake breeze pushes you forward, the shoreline changes from towering cliffs to open waterfront parkland, offering views that demand your attention—not just as background scenery but as active players in this aquatic adventure. The water, ever dynamic, shifts from placid to choppy, requiring paddlers to stay alert and adjust stroke and stance accordingly.

Gear up for this event with practical precision. Choose a stable kayak or canoe to handle shifting waves and bring a good-quality life jacket, hydration pack, and layered clothing adaptable to sudden temperature changes on the water. Timing is critical: set out early to avoid afternoon winds that can whip the lake into more unpredictable moods. Participants typically finish in 3 to 4 hours depending on skill and conditions.

Besides the physical challenge, the Paddle-In is a social occasion anchored by local culture. After paddling, expect to find local food vendors, live music, and community groups sharing stories and gear tips on the beach—making this a full-day affair that balances activity with relaxation.

For those planning to join, note the elevation gain is minimal since the route is water-based, but the water’s varying temperament demands fitness and readiness. Shore access points along the route provide spots to rest or regroup but expect the lake to assert itself as a force to respect, invigorate, and understand.

Whether you’re paddling solo or with a group, the Annual Cherry Beach Paddle-In offers an accessible yet invigorating way to interact with Lake Ontario’s shoreline. It’s a rare chance to feel the water’s pulse, discover new routes, and appreciate Scarborough’s outdoor charm without leaving the city’s orbit.