Trail Running calendar near Websterville 2026-2027

Run rugged singletrack to Mount Moosalamoo in Goshen Vermont with Lake Dunmore views, choosing 14 mile or 36 mile distances that test your climbing legs. Entry includes a shirt, postrace meal, finishers award and primitive camping.

Jigger Johnson Ultras offers rugged, technical trail races in New Hampshire's White Mountain National Forest, August 14 to 16, 2026. Choose 20, 50 or 100 mile routes that test navigation, endurance and reward big mountain views.

Run the Triple Dam 10K in Perkinsville VT on a scenic loop of grassy trails, dirt roads and a shallow river crossing. Open to runners and walkers, this fundraiser for Springfield XC finishes by a swimming hole with post race treats.

Join the Black Bear Trail Races in Waterville Valley on Aug 29, 2026. Distances range from a rugged 50K with big climbs to a family friendly 1 mile fun run on beautiful single and double track trails.

Trek Cannon Mountain in Franconia New Hampshire and choose 7, 14, 21 or 28 mile routes with ten hours to finish. Rugged trails, sweeping White Mountain views, camaraderie and a post trek gathering with proceeds benefiting conservation.

Run the rugged Kilkenny Ridge in the White Mountain National Forest with 50 mile, 25 mile or 25K options over remote, scenic summits and huge climbs. The unmarked course requires GPS, mandatory gear and carries limited aid.

The Tam Trek will take place in Middlebury on Sunday 20 September 2026. You can run between 5 and 19 miles.

Tackle five Vermont peaks at the Westmore Mountain Challenge on September 26, 2026, a community focused mountain marathon that benefits NorthWoods Stewardship Center. Choose the full marathon or 20 mile trail course and savor rugged single..

The Vermont 50 is a classic late September mountain bike and ultra run at Mount Ascutney offering 50 mile and 50K options, plus family fun and kids activities on Saturday. Proceeds support Vermont Adaptive Ski and Sports.

Run wooded trails at Amy's Park in Bolton Landing with 4.5 mile and 10 mile options or run virtually. Proceeds support the Lake George Land Conservancy and its work protecting wetlands and watersheds.

Devil's Den Ultra near Bradford VT challenges runners with a rugged 10K loop offering 30 hour, 12 hour and 10K options on rocky, rooty mountain trails. Entries are capped at 100 and registration opens Jan 1 2026.

Join the von Trapp Mountain Marathon in Stowe Vermont with full and half marathon options on a rugged 13.1 mile loop. Steep climbs, a scramble to Round Top and sweeping views of Mount Mansfield create a rewarding mountain trail.

Run the Ghostly Gallop Trail 5K in Milton VT on October 25. This Halloween themed, costume friendly trail race on Laura's Tears at Arrowhead Golf Course offers prizes, post race refreshments, and family friendly fun for ages 12 and up.

UltraTrax Burke Mountain is a timed trekking challenge on scenic trails across Burke Mountain. Choose 7, 14, 21 or 28 miles and finish within 10 hours to earn a shirt, patch and longer distance medals, plus post trek food and activities.