Pittsfield
Trail Running Calendar near Pittsfield 2026-2027
Explore the top trail runs near Pittsfield for 2026-2027! We've gathered 19 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
November 2026
Hourly 2.25 mile laps gaining about 1,209 feet near Brownsville VT until one runner remains, with an aid station, camping options, and possible winter conditions.
February 2027
Multi-day winter endurance race at Riverside Farm in Pittsfield, VT on Feb 18 to 20, 2027; unknown start and end times, snow terrain, heavy obstacles, entry by application.
April 2027
Runamuck 50K in South Pomfret VT is a mostly dirt road ultramarathon at Saskadena Six with 3,726 feet of climb, multiple aid stations, and an eight hour cutoff.
May 2027
A 10K trail run through Marsh-Billings-Rockefeller National Historic Park in Woodstock VT with rolling terrain and proceeds benefiting The Community Campus.
A multi-distance trail ultra at Riverside Farm in Pittsfield, Vermont featuring 10M, 50K, 50M, 100M and 200M courses on rugged 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 obstacle course endurance event at Riverside Farm in Pittsfield, Vermont from June 23 to June 26, 2027; participation requires an application.
Three-stage Hurricane Heat endurance event at Riverside Farm in Pittsfield VT with 4 hour, 12 hour and 24 hour options and more than 40 challenges.
Endurance event at Riverside Farm, Pittsfield VT offering a 24 hour challenge and Last Spartan Standing format with repeated 2 mile loops and 970 feet gain every 45 minutes.
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.
Endurance weekend at Ascutney Outdoors with 50 mile and 50 km runs, mountain bike options, relays, and kids races supporting Vermont Adaptive.
October 2027
Point to point 10K downhill on the Northern Rail Trail along Mascoma Lake and River in Lebanon NH on October 9 2027, part of the Upper Valley Running Series.
Time based trail ultra in South Royalton, VT on October 16, 2027 featuring a 3.8 mile loop with 570 ft gain and 6 hour and 12 hour options.