Jackson
Trail Running Calendar near Jackson 2026-2027
Explore the top trail runs near Jackson for 2026-2027! We've gathered 13 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
September 2026
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.
A memorial family fun run and kids dash on scenic trails at White Mountains Regional High School, featuring prizes, music, a participant brunch, and a scholarship fund.
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 mountain race in Bridgton featuring technical single track trails and significant elevation gain across the iconic ridge of Pleasant Mountain.
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 community race day in Waterville Valley offering a 10 mile trail race, a mostly flat 5K road race, and a 1 mile kids run during the town's fall festival.
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 event in Jackson, NH with a 5 km turkey trot and a 1 km kids fun run, plus awards and local school beneficiaries.
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.
August 2027
Multi-distance trail ultras in the White Mountains centered on Waterville Valley with long mountain routes, large elevation gains, strict mandatory gear, and limited crew access.