Pittsfield
Trail Running Calendar near Pittsfield 2026-2027
Explore the top trail runs near Pittsfield 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
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.
September 2026
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.
Trail races at Paine Mountain in Northfield VT featuring a 7.5 mile summit course, a 6K Anchor route, and free youth races supporting local trail management and XC programs.
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.
May 2027
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 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.