Middlebury
Trail Running Calendar near Middlebury 2026-2027
Explore the top trail runs near Middlebury for 2026-2027! We've gathered 8 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
August 2026
September 2026
Scenic 5K cross-country and a 2 Mile fun run/walk at Crown Point State Historic Site supporting online safety awareness and the NYS Parks wellness challenge.
A 3.1-mile race at Shelburne Farms on 09/27/2026 with a course that mixes gravel paths (not loose), wooded trails, fields and dirt roads. Field limited to 200 racers; registration through Racevermont.com includes a finishers medal.
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.
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