Trail Running calendar near Chelsea 2025-2026

Explore Waterville Valley trails at the Black Bear Trail Races on August 29. Choose from a family friendly 1 mile fun run up to a challenging 50K around nearby 4,000 foot peaks, with finishers awards, post race snacks and a finish festival.

Take on the Kilkenny Ridge Race in the White Mountain National Forest, a remote, rugged traverse of peaks including Mount Cabot and Mount Waumbek. Choose 50 Miler, 25 Miler or 25K and come prepared with navigation and mandatory gear.

Run the Westmore Mountain Challenge in East Charleston, Vermont, a rugged trail marathon that crosses five peaks over 26 miles and 6,100 ft of climbing. Shorter distances and limited entries create a scenic, low impact mountain experience.

Challenge yourself at the Vermont 50, a legendary mountain bike and ultra run at Ascutney Outdoors. Join racers, relays, vendors and kids fun races while supporting Vermont Adaptive on Sept 27, 2026.

Amy's Adventure Race for the Lake features scenic 4.5 mile and 10 mile trail courses through Amy's Park with ponds, marshes and about 700 feet of climbing. Proceeds benefit Lake George Land Conservancy and virtual entries are welcome.

Run the Trapp Lodge Mountain Marathon in Stowe, Vermont, with marathon and half options on a scenic 13.1 mile loop through Green Mountains trails. Expect steep climbs, scrambling and big elevation changes amid Vermont views.