Pittsfield
Trail Running Calendar near Pittsfield 2026-2027
Explore the top trail runs near Pittsfield 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.
October 2026
A traffic-free point to point 10K on the Northern Rail Trail along Mascoma Lake and the Mascoma River with bag drop, finish parking, and modest awards.
A family-friendly 5K walk or run at Billings Farm & Museum in Woodstock, VT with live music, cider donuts at the finish, prizes, and museum admission included.
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.
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.
May 2027
Trail ultramarathon at Riverside Farm in Pittsfield VT offering distances from 10 miles to 200 miles through Green Mountain terrain.
A multi day trail running festival in Ripton, Vermont featuring races from a 9 mile course up to multi day marathon series and ultra distances. Held at Silver Towers Camp in Green Mountain National Forest with on site camping for a small fee.
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 marked 5k trail run and walk on July 4 in Rochester starting and finishing at River Brook Park, following single-track trails through Chantrea Field and the VCR Connector.
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.