Woodstock
Trail Running Calendar near Woodstock 2026-2027
Explore the top trail runs near Woodstock for 2026-2027! We've gathered 17 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
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
February 2027
A multi-day winter endurance race in Pittsfield, VT with snow terrain, physical obstacles and unknown start and end times; entry is by application only.
April 2027
A 50K trail race at Saskadena Six in South Pomfret, VT on April 10, 2027, featuring hilly dirt roads, 3,726 ft of gain, variable weather, and an 8 hour cutoff.
May 2027
A multi-distance trail ultramarathon at Riverside Farm in Pittsfield, Vermont, offering 10M, 50K, 50M, 100M and 200M races on Green Mountain trails.
June 2027
A 72-hour application-only endurance obstacle race held June 23–26, 2027 at Riverside Farm in Pittsfield, VT, with team options and a GOVX service-member discount.
A three-stage Hurricane Heat endurance event at Riverside Farm in Pittsfield VT offering 4 hour, 12 hour, and 24 hour options with tickets from USD 79.
An endurance event at Riverside Farm in Pittsfield VT offering a 24 Hour Challenge and a Last Spartan Standing format with 45 minute loop intervals and 970 feet of gain per loop.
Cirque Series at Killington is an 8.2 mile trail race with 3,010 feet of vertical gain, featuring Sport, Expert and Pro divisions and gear and cash prizes.
July 2027
A community 4th of July 5k trail run and walk in Rochester, VT with a well marked course on single track and connector trails.
A two day trail relay at Ascutney Outdoor Center with single track and switchbacks, camping options, and team formats for 2 to 8 runners.
July ultramarathon in Vermont offering 100 mile and 100 kilometer options, 17,000 feet of climbing, with proceeds supporting Vermont Adaptive Ski and Sport.
September 2027
Obstacle course weekend at Killington Ski Resort on Sep 18 to 19, 2027 with Sprint 5 km, Beast 21 km, Ultra 50 km and Kids races.
October 2027
A 10K point to point downhill run along Mascoma Lake and the Mascoma River on the Northern Rail Trail in Lebanon NH on October 9, 2027.