Killington
Trail Running Calendar near Killington 2026-2027
Explore the top trail runs near Killington for 2026-2027! We've gathered 20 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
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
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.
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.
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 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 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 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.
July ultramarathon in Vermont offering 100 mile and 100 kilometer options, 17,000 feet of climbing, with proceeds supporting Vermont Adaptive Ski and Sport.