Chester
Trail Running Calendar near Chester 2026-2027
Explore the top trail runs near Chester for 2026-2027! We've gathered 14 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
August 2026
Timed 6 hour and 12 hour loop races in Chester, Vermont on mixed single and double track trails with basic aid and town park amenities.
Trail races at Okemo's Jackson Gore area feature a 7.6 mile summit course with 2500 vertical feet plus short family fun runs, post-race lunch and awards.
A summit trail race on Stratton Mountain with youth and open distances, prizes, raffle awards, and proceeds supporting the SMST2 professional ski team.
A 4.61 mile trail race at Moody Park in Claremont NH featuring narrow single track, wet sections and a steep drop and climb at Gravity Cavity. The event is part of the Western NH Trail Running Series and benefits the local parks department.
A 10 km trail loop in Perkinsville VT along the Black River with a shallow river crossing, mixed grassy trails and dirt roads, and post run refreshments.
September 2026
Three community races at Springfield Dam include a free kids 0.5 mile, a 1 mile Maniac Mile for ages 10 and up, and a scenic 3.1 mile course with trails, food vendors, and family activities.
Pisgah Mountain Trail Races in Chesterfield, NH offers 50k and 23k mountain trail ultraruns on Sunday 9/13/26. Aid stations provide LMNT, Tailwinds, and Untapped and proceeds support New Hampshire Special Olympics.
Mountain bike and ultra-run event at Ascutney Outdoors near West Windsor VT with 50 mile and 50K options, relays and kids races, benefits Vermont Adaptive.
October 2026
A 4.9 mile mountain trail race in Keene, NH featuring four up and down laps on varied ski and single-track trails, with proceeds and food donations benefiting the Keene Community Kitchen.
November 2026
A Last Person Standing mountain event with hourly 2.25 mile laps that climb about 1,209 feet each. Aid, hot food, camping, elevation milestone prizes, and awards are provided; conditions may include cold, snow, or ice.
July 2027
Trail relay held in July at Ascutney Outdoor Center in Brownsville VT featuring multi-runner team divisions, single track trails, camping and glamping options.