Middlebury
Trail Running Calendar near Middlebury 2026-2027
Explore the top trail runs near Middlebury for 2026-2027! We've gathered 12 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
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 Shaw Outdoor Center Northfield VT on Sep 27 2026 featuring a Paine Summit 7+ mile and a 6k Anchor Challenge with a 4-person team option.
October 2026
February 2027
A multi-day winter endurance race in Pittsfield, Vermont with snow-covered trails, physical obstacles, problem-solving tasks, and continuous efforts that can run 40 hours or more.
May 2027
Bloodroot Ultra is a multi distance trail event May 5 to 8, 2027 in Pittsfield Vermont featuring races from 10M to 200M on Green Mountain trails.
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 in Pittsfield, Vermont from June 24 to 26, 2027 at Riverside Farm, with team entry options and a service member discount.
A three stage Hurricane Heat endurance event at Riverside Farm on June 25 to 26, 2027 offering 4 hour, 12 hour, and 24 hour options with an 18 plus age requirement.
Two endurance formats at Riverside Farm VT: a 24 hour loop challenge and Last Spartan Standing with 45 minute laps of about 2 miles and 970 feet gain.
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.