Trail Running calendar near Appleton 2026-2027

Join Hope in Motion 2026 in Caledon East for a day of cycling, running, and walking to support mental health services. Choose from distances up to 100 km and help make a direct impact in the Peel Dufferin community.

Experience an evening trail run through Mendon Ponds Park with 4 mile and 8 mile options. This self-sufficient race features a loop course through scenic meadows and eskers followed by a post-race cookout.

The Boomerang Trail Run is a 7 km looped trail race in the hills of Batawa, Ontario. Choose your challenge by running as many laps as you can in 2, 4, or 6 hours. The event has a relaxed vibe, with a cup-less aid station and manual lap timi..

The Northumberland Run Forest Run offers four trail challenges on June 14, 2026. Choose from a 4-hour 3 km loop, a 7.5 km loop, a 9 km loop, or a combined 24.6 km course through the forest. This is a self-supported event with a relaxed, "Fo..

The 19th Uxbridge Run for the Diamond offers 5K and 10K trail run/walk events and a Kids Dash. Proceeds benefit the local hospital, and adult participants are entered into a special diamond draw.

Many On The Genny is a 45-mile trail ultra taking runners along both sides of Letchworth State Park's famed gorge. The course features beautiful vistas, steep climbs, and remote sections where self-sufficiency is key. It offers both a solo..

The Whole Enchilada is a trail running event set in Durham Region, Canada's trail capital. It features distances from a 1 km fun run to a demanding 50 km route. The race focuses on sustainability, being cup-free and supporting local environ..

Trail running event at Kelso Conservation on June 27, 2026 offering 2K, 5K, 10K, MAX Elevation and a 20K relay. Courses include aid stations, professional chip timing and a post event village with awards.

Run through the night at the Dark & Dirty trail event in Batawa. Choose between a 7 km or 14 km course on marked, technical trails where a headlamp is required. All finishers get a medal, and there are prizes for top performers.

A point-to-point trail adventure on Ontario's iconic Bruce Trail. Choose from three distances, exploring unique conservation areas and historic trail sections. This grassroots event supports trail maintenance and offers a true back-to-natur..

Run or walk through the historic Liberty Vineyard & Winery. Choose a 5K for a finisher medal and finish line wine, or a leisurely 1K with four wine tastings. Enjoy an after party with games, contests, and food trucks at this scenic family f..

The Webster Trail Classic is a scenic trail run through three distinct parks in Webster, NY. Runners can choose between a 10-mile or a 3.5-mile course, each offering varied terrain. A free kids fun run is also part of the event.

The Mighty Mosquito Trail Race in Mendon Ponds, NY offers a weekend of trail running with distances from 5 to 100 miles, plus relay options. The event features solo and team formats, including a unique nighttime 50K. All proceeds support th..

Run a 7 km loop through the Carolinian forest of Dundas Valley. Choose from distances ranging from a single loop to a 100-mile ultra or the unique "Gong Show" elimination race. All finishers get a medal, and early registrants receive a race..

Run steep ski slopes at Swain Ski Resort in a mountain trail race with two loops and nearly 2,500 feet of climbing, including the Robinson ascent. Enjoy post race food and drinks and chase championship and age group prizes.

The Beast of Burden - Summer is an ultra-marathon on New York's historic Erie Canal towpath. Runners can tackle 100, 50, or 25 mile distances on a course featuring fully stocked aid stations. A special buckle awaits those who conquer both t..

The 5 Peaks Albion Hills trail run takes place in the scenic Albion Hills Conservation Park. With distances from 7.5 km to 22.75 km, it offers singletrack trails and family-friendly activities like camping and a pool.

This 5K trail run and 2-mile walk supports the Bread of Life Outreach Center at Sprague Brook County Park. The event features professional timing and a post-race celebration with a wellness fair. The first 100 registrants receive a special..

A hybrid in-person and virtual fundraiser on September 13, 2026 in Henrietta NY, offering 5k and 10k options to support ROCovery's recovery programs and remember lives lost. Early bird registration and race swag are available.

Run through the scenic "Grand Canyon of the East" at Letchworth State Park. Choose a 5K or 10K trail course, both starting near the Trout Pond. All finishers receive a medal and post-race food.