Trail Running calendar near Chester 2026-2027

A timed walking and trekking event on Cannon Mountain in Franconia, NH with 7, 14, 21, and 28 mile loop options across forest, rocky scrambles, and ridgelines. Optional weighted vests are allowed and finishers within 10 hours earn patches o..

Wilcox Wild on September 6, 2026 in Stony Creek New York is a 31 miles trail ultra that loops from Harrisburg Lake to Wilcox Lake via scenic singletrack and waterfalls. Limited entries require prior experience and include a catered post rac..

A trail race in Hooksett on September 19, 2026, featuring a 5k on stone dust and wooded conservation trails and a half mile kids run for ages 12 and under. Proceeds support Hooksett Kiwanis community and youth programs.

A community trail race on September 20, 2026 offering a 19 mile course, 10K and youth 10K, a 5K, and a 2 mile fun run around Wright Park in Middlebury, Vermont.

The Vermont 50 offers rugged 50 mile mountain bike and ultrarun courses around Mount Ascutney in West Windsor, Vermont. Held each September, it raises funds for Vermont Adaptive Ski and Sports and includes relays, a 50K and kids activities.

The Amy's Adventure Race for the Lake will take place in Bolton Landing on Saturday 3 October 2026. You can run between 5 and 10 miles.

Take on Flutters and Foliage Endurance Race in Cohoes NY on Oct 3 2026 with 6 hour, 3 hour and 1 hour solo options plus relays and vendors. Family and dog friendly, proceeds support Flutters of Hope and eating disorder services.

Run the winding single lane trails of Groton Town Forest with a choice of 9.5 mile or 3.4 mile courses featuring roots, rocks and rolling climbs. Limited to 250 runners, this community race supports Groton trail maintenance and finishes wit..

Enjoy autumn trails at the Keene Family YMCA Fall Foliage Trail Races on October 4, 2026, with 5K and 10K options around scenic Keene, NH. Run for community impact while enjoying chip timed courses and seasonal views.

Run a point to point ultramarathon on the Midstate Trail across Massachusetts with crossings into NH, RI and CT. Choose 100 Mile, 50 Mile or 50K routes through woodlands, fields and rivers at peak fall.

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.

An annual October trail event on the Granite Town Rail Trail near Brookline and Milford, NH, offering distances from 7.5 miles to a 30-hour ultramarathon. Proceeds support local Conservation Commissions for trail maintenance.

Krampuslauf at Dartmouth Skiway brings a Central European Krampus run to New England with 5K, 10K, and a 9 hour 10K lap option. Finishers receive medals and lap runners earn pins and a 50K medal.