Woodstock
Trail Running Calendar near Woodstock 2026-2027
Explore the top trail runs near Woodstock for 2026-2027! We've gathered 16 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
October 2026
Blackhawk Blaze in Meriden, NH on October 4, 2026 offers a 1 mile fun run plus a 5K trail and a virtual 5K, with proceeds supporting Plainfield school programs.
A traffic-free point to point 10K on the Northern Rail Trail along Mascoma Lake and the Mascoma River with bag drop, finish parking, and modest awards.
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.
November 2026
A Last Person Standing mountain event with hourly 2.25 mile laps that climb about 1,209 feet each. Aid, hot food, camping, elevation milestone prizes, and awards are provided; conditions may include cold, snow, or ice.
December 2026
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
Trail ultramarathon at Riverside Farm in Pittsfield VT offering distances from 10 miles to 200 miles through Green Mountain terrain.
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.
September 2027
Obstacle course weekend at Killington Ski Resort on Sep 18 to 19, 2027 with Sprint 5 km, Beast 21 km, Ultra 50 km and Kids races.