West Windsor
Trail Running Calendar near West Windsor 2026-2027
Explore the top trail runs near West Windsor for 2026-2027! We've gathered 16 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 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 family friendly 5K on the Webb Forest trails organized by Wilmot Learning Place, featuring a signed course, water stations, timing for runners, post-race recognition, and nearby parking with overflow at local fields.
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.
An obstacle course weekend at Killington Ski Resort on Sep 19 to 20, 2026 featuring Sprint, Beast, Ultra and kids races with spectator access.
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 community run on October 10, 2026, organized by the Lebanon Recreation, Arts, and Parks Department, following the Rail Trail from Enfield along Mascoma Lake and the Mascoma River to a finish in Lebanon. Fees change before race week and parking is a..
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.
December 2026
June 2027
A multi-day trail ultramarathon in Pittsfield, Vermont featuring distances from 10 miles to 200 miles on Green Mountain trails with mandatory headlamps for the longest events.
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.
July ultramarathon in Vermont offering 100 mile and 100 kilometer options, 17,000 feet of climbing, with proceeds supporting Vermont Adaptive Ski and Sport.