Trail Running calendar near Appleton 2026-2027

Join the Dion Mighty Chickadee Snowshoe Race at Cold Creek for a scenic 6.5 km through forest and meadow with a few climbs. Limited entries, snowshoe rentals and post run food plus awards make this a fun winter challenge.

Shake off winter with the Old Man Winter Trail Race at Marjim Manor, a scenic 3.2 miles through winery grounds and apple orchards on January 24, 2026. Register by Jan 16 for a special embroidered hat, chip timing, finish photos, and awards.

Experience a winter trail challenge on January 31, 2026 at Mendon Ponds Park, with a scenic loop around Devil's Bathtub and warm aid station comforts at Hopkins Point Lodge. Choose from 50k, 25k or 5 mile options as part of the Common Groun..

Beast of Burden Winter is a chilly ultramarathon in Lockport, NY with 25, 50 and 100 mile options on February 7, 2026. Run the scenic Erie Canal towpath where snow is possible and enjoy warming shelters and hot aid station fare.

Shake off winter with the Cabin Fever Trail Races at Webster Park, offering 5 and 10 mile trail loops through scenic, rolling terrain. Expect variable winter trail conditions, warm post race food, and a friendly community vibe.

Run the DSpring Fling 5 km along Hamilton's scenic waterfront and Bayfront Park on a flat, traffic free, fan friendly course. Enjoy chip timing, a custom finisher medal and post race food and photos.

Run a scenic 5K through trails and vineyards at Spring Lake Winery in Lockport on April 4, 2026. Enjoy finish line snacks, a keepsake wine glass, and post race food and drinks with live music and festivities.

Challenge yourself on the Foxtail Rail Trail Race in Dundas Valley, offering 5, 10, 25 and 50 km options on a fast, wide rail trail with start and finish at the Trail Centre. Enjoy aid stations, chip timing, race photos and finisher medals..

DENFIT ULTRA at Buffalo Ski Center is a 10 km ski slope loop with 50k or 100k options, offering big elevation and possible snow. Parts are unlit so headlamps are required and finishers earn medals and custom spears.

Join the 5 Peaks Trail Running Series at Kelso in Milton for forest trails with steep climbs and flowing descents. Pick distances from kids races to 20.6 km and enjoy scenic singletrack, aid stations and a lively finish.

Hit the trails at Medved Madness in Mendon Ponds Park with long, short and kids course options. Long and short finishers receive gender specific technical shirts and everyone can unwind at an after race barbecue.

Explore the Seaton Scramble Trail Race in Pickering on May 9, 2026 with scenic single and double track, creek crossings, stairs and viewpoints. Distances from a kids 1K to a challenging 50K suit every trail runner.

The First Hour : event details The First Hour is the first event in the Happy Hour Friday Night Series. It takes place on May 15, 2026, at Goodrich-Loomis Conservation Area in Castleton, Ontario. The event is organized by Dirty Soles Trail..

Run Letchworth State Park's dramatic gorge at the Sehgahunda weekend, with distances from 5K and relays to a two day 72K. Cup free aid stations, post race food, event shirts and unique finisher items await.

Run through Letchworth State Park at the Vale of Three Falls on May 17, 2026, choosing from 5K, 10K, or 15K distances. Expect rolling hills, scenic Genesee River overlooks on stone and gravel roads, and a festive finish at the Parade Ground..

Sulphur Springs Trail Race in Dundas Valley, Hamilton on May 23 and 24 offers looped 20K terrain with distances from 10K to 100 miles plus team relays. Rugged trails, big climbs, and crew access make for a classic spring ultra.

UltraTrax Holiday Valley is a timed outdoor trek across wooded single track trails and ridgelines at Holiday Valley, with options from 7 to 28 miles and a 10 hour cutoff. Enjoy a marked course, finishers gear and a post trek party with food..

Join Hope in Motion 2026 on June 7 in Caledon East for a community fundraiser supporting CMHA Peel Dufferin with cycling, walking, running and rolling for all abilities. Choose distances from 5 km trails to 100 km rides and help raise funds..

Test your endurance at the Boomerang Trail Run on June 13 at Batawa Ski Hill and complete as many 7km+ loops as you can in 2, 4 or 6 hours. Techy trails, hills and a midway aid station make for a rugged, social challenge with limited spots.

Run scenic Northumberland forest trails on Sunday June 14, 2026 while supporting St. John Ambulance. Choose 3 km, 7.5 km, 9 km or a 24.6 km self supported course and grab one of just 100 spots.