West Windsor
Trail Running Calendar near West Windsor 2026-2027
Explore the top trail runs near West Windsor for 2026-2027! We've gathered 21 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
August 2026
A 10K trail loop along the Black River in Perkinsville, VT with a shallow river crossing, post-race swim access, and proceeds supporting Springfield High School Cross Country.
September 2026
Three community races at Springfield Dam include a free kids 0.5 mile, a 1 mile Maniac Mile for ages 10 and up, and a scenic 3.1 mile course with trails, food vendors, and family activities.
Trail event at Ascutney Outdoors with a timed 3.2 mile 5K and a 1 mile option supporting Lucy Mackenzie Humane Society; dogs welcome.
A roughly 5.5 mile trail run at Farnum Hill Preserve on September 12, 2026, featuring a fast opening section, steep climbs, ridge running, and proceeds for local trail development.
A weekend of mountain obstacle races at Killington Ski Resort with Sprint, Beast, Ultra, kids races, and spectator access on September 19–20, 2026.
Mountain bike and ultra-run event at Ascutney Outdoors near West Windsor VT with 50 mile and 50K options, relays and kids races, benefits Vermont Adaptive.
October 2026
Fourth annual CLTA 5K honors a Purple Heart recipient and USAF Major General with a trail course through fall foliage near Manchester, Vermont.
Blackhawk Blaze in Meriden NH on October 4, 2026 features a 5K trail on French's Ledges, a 1 mile fun run, and a virtual 5K with proceeds to local school groups.
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.
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
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.
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.
An 8.2-mile trail race at Killington, VT on June 26, 2027 with 3,010 ft of ascent, multiple divisions, prizes, and a 500-entry cap.
July 2027
A multi day trail relay at Ascutney Outdoor Center in Brownsville, VT, featuring 118 miles of single track, switchbacks, riverside views and on site camping and glamping options.