Middlebury
Trail Running Calendar near Middlebury 2026-2027
Explore the top trail runs near Middlebury for 2026-2027! We've gathered 13 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.
Experience the Anchor Challenge at Norwich University with a summit trail run or a 6k team race on the scenic Paine Mountain trail system.
October 2026
Dog friendly 5K and 10K trail runs at Bolton Valley Resort in Vermont on October 3, 2026, with mixed mountain and ski trails and on course medical support.
February 2027
Multi day winter endurance race in Pittsfield, Vermont (Feb 18 to 20, 2027) on snow covered terrain; entry requires application and acceptance to receive a ticket code.
May 2027
Experience the original Spartan Trail race at Riverside Farm with distances ranging from 10 miles to a 200 mile ultra through the rugged Vermont Green Mountains.
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 endurance obstacle course event in Pittsfield, Vermont from June 23 to 26, 2027, requiring prior application and acceptance for ticket access.
A three stage Hurricane Heat endurance event at Riverside Farm near Pittsfield, VT offering 4 hour, 12 hour, and 24 hour options with 40 plus challenges and age 18 plus.
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.
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.