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Trail Running Calendar near Conway 2026-2027

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Explore the top trail runs near Conway for 2026-2027! We've gathered 12 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.
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.
Mountain up-and-down race at Cranmore Mountain in North Conway offering 10 km and 5 km options, USATF sanctioned and $7,500 in prize money for 2026.
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
Night mountain race at Cranmore Resort offering 5 km and 10 km courses marked with reflective flagging and LED lanterns; headlamps required.
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.
August 2027
A trail 5K through Wanakee campland on August 14, 2027, supporting the camp scholarship fund and followed by a Homecoming BBQ and awards ceremony.
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.
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