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Trail Running Calendar near Chatham 2026-2027

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Explore the top trail runs near Chatham 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.

October 2026
Trail 5k in Oxford, Maine with in person and virtual options, starting and ending at Oxbow Beer Garden to benefit Mission Working Dogs.
The 26th North American Wife Carrying Championship returns to Sunday River in Newry, Maine on October 10, 2026. Teams of one man and one woman race a 278 yards obstacle course with log hurdles, a sand trap, and the Widow Maker water hazard.
A set of road, trail and kids races in Waterville Valley on October 11, 2026, featuring a scenic 10 mile trail with mountain views and a mostly flat 5K.
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
An evening mountain race at Cranmore Resort offering 5 km and 10 km courses with marked trails and required headlamps.
A trail-based 5 km and a 1 km kids fun run in Jackson, NH with staging and parking at Eagle Mountain House, awards for top finishers, and local school beneficiaries.
May 2027
Timed trail racing on a slightly technical 2.0 mile single track loop at White Lake State Park with 6, 12 and 24 hour options and on-site aid and crew areas.
June 2027
A 23K mountain trail race in Tamworth, New Hampshire with about 4,500 to 4,800 feet of elevation gain and technical, rocky summit terrain.
July 2027
A 5K obstacle course at Sunday River Resort in Newry, Maine, featuring ski-trail and wooded terrain with custom built obstacles.
29 km and 14 km trail races in the White Mountain National Forest featuring exposed ledges, scrambling, mandatory mountain safety gear and specific aid station rules.
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.
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