Trail Running calendar near Chester 2025-2026

Run single track up to Mount Moosalamoo with lake views at the Moosalamoo Ultra in Goshen Vermont on August 1, 2026. Choose 14 miles with 2400 feet climb or 36 miles with 5000 plus feet for a rugged Green Mountain challenge.

Join the Sweltering Summer Ultra, an 8 hour track challenge at Clapp Park in Pittsfield where runners and walkers lap a cinder loop and hit a marathon split. Chip timing, live leaderboard, refreshments and awards support the AYJ Fund.

Run the Jigger Johnson Ultras in Waterville Valley, NH, across rugged White Mountain trails and exposed ridgelines for an epic mountain challenge. Multiple distances demand GPX navigation and mandatory gear for remote and night sections.

Run the Triple Dam 10K in Perkinsville VT on August 23, 2026 for a scenic road and trail loop with a fun calf deep river crossing. Open to runners and walkers, proceeds support Springfield High School cross country.

Take on the Black Bear Trail Races in Waterville Valley on August 29, 2026, with distances from a rugged 50K circling 4,000 foot peaks to a family friendly 1 mile fun run. Scenic trails, big climbs, and alpine views await runners of all lev..

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.

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.

Run scenic, rooty trails in Groton Town Forest on October 4 with 9.5 mile and 3.4 mile options through rolling hills and rocks. Limited to 250 runners with refreshments and awards.

Hit the trails at the Keene Family YMCA Fall Foliage Trail Races in Keene, NH on Sunday, October 4, 2026, with 5K and 10K options through scenic fall woods. Enjoy chip timing, shirts for early registrants, and support local YMCA programs.

Tackle the Midstate Massive Ultra Trail, a UTMB Index point to point across New England following the historic Midstate Trail. Choose 100 mile, 50 mile or 50k routes through mountains, fields, roads and rivers for a multi state adventure.