Vermont
Vermont Trail Running Calendar 2026-2027
Explore the best trail runs in Vermont for 2026-2027! Our updated list features 34 exciting trail runs across the region. Find your next trail run in Vermont below and join the trail community at these great events!
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.
A historic ski race from Mt. Mansfield to Stowe Village with 6 km and 20 km divisions in classic, skate, and fixed heel formats.
May 2027
Trail ultramarathon at Riverside Farm in Pittsfield VT offering distances from 10 miles to 200 miles through 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 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.
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 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.
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.
Test your endurance on a 1 mile loop at Northeast Slopes in this last runner standing event honoring the legacy of the Magnificent Bastards Marine battalion.
September 2027
Jay Peak Trail Running Festival in Vermont offers seven races over Labor Day weekend, from a kids trail race to a 53.1 km ultra with 9000+ ft elevation.