Rochester
Trail Running Calendar near Rochester 2026-2027
Explore the top trail runs near Rochester for 2026-2027! We've gathered 15 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
September 2026
A two day Spartan obstacle race weekend at Killington Ski Resort featuring Sprint, Beast, Ultra and kids races on steep, off trail mountain terrain.
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
A family friendly 5K walk or run at Billings Farm & Museum in Woodstock VT with live music, a cider donut at the finish, and awards for top finishers and best costumes.
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.
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.
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.