Jackson
Trail Running Calendar near Jackson 2026-2027
Explore the top trail runs near Jackson 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.
August 2026
Trail races in Waterville Valley NH with 50K, 23K, 4 mile and 1 mile options, cup less aid stations, required 50K gear, and finisher awards.
September 2026
A weekly fall trail running and walking series at Great Glen Trails in Gorham, NH from Sep 3 to Oct 8, 2026. Choose from 5 km, 3 km or 1.5 km courses; dogs on leash are welcome and one-time entries are available on-site.
Whites 100 is a noncompetitive trail event on September 11, 2026 in Shelburne NH offering five drop bag stations, transport, and required Garmin inReach.
A mountain footrace from the Mount Washington Cog Railway base to the summit with 2.75 mile climb or a 5.5 mile roundtrip across steep, rocky, and exposed terrain.
A 5K trail race at Loon Mountain on September 20, 2026, as part of the 51st NH Highland Games, with 800 ft of elevation gain across dirt trails, service roads and ski trails. Registration includes a race shirt and festival admission.
A one lap up and down mountain race in Waterville Valley, New Hampshire on September 20, 2026, part of the USATF-New England Mountain Racing Circuit. The course uses grassy ski slopes and gravel service roads and includes three aid stations.
Charity 5K run/walk at Castle in the Clouds supporting the New Hampshire Humane Society, a 3.2 miles course on trails and roads with awards, superhero swag, and leashed dogs welcome.
A 21k trail race on Pleasant Mountain in Bridgton ME featuring technical single-track, significant climbs, one aid station, post-race food and beer, and proceeds supporting land conservation.
October 2026
A last person standing trail ultra in Center Conway NH on October 3, 2026 run on a 3.5 mile forest loop with a minimal aid station, camping option, and a Sunday Beer Mile.
A rugged self supported 10 km trail race in the Great North Woods near Randolph, New Hampshire, run without aid stations and requiring a mandatory gear list.
November 2026
Thanksgiving morning trail 5k and a kids 1k in Jackson, NH, through nordic trails and Eagle Mountain House, with proceeds supporting local youth programs.
June 2027
A 6.9 mile trail race at Cannon Mountain with 3,080 feet of vertical gain, multiple divisions with cash and gear prizes, and season points toward a PEAK FREAK buckle.