Trail Running calendar near Chatham 2026-2027

A weekly Tuesday cross country series in Craftsbury, VT from June 9 to August 25, 2026, with two 5 km courses, kids courses, and a bike race. The series is free for all and uses single track and ski trails; weather and air quality guide can..

A 6.9 miles mountain trail race at Cannon Mountain, New Hampshire with 3,080 ft of elevation gain and a summit at 4,031 feet. The route features a 2 mile Kinsman Ridge section on steep technical trails and a strict 2 hour summit cutoff.

A community fun run on 06/13/2026 behind Madbury Town Hall with a 1K kids run and a 5K route through Kingman Farm trails. Registration is free and donations for park improvements are accepted on the day.

A mountain footrace beside the Mount Washington Cog Railway offering a 2.75 mile summit climb or a 5.5 mile roundtrip, steep grades and boulder fields, and highly variable summit weather.

A six hour endurance event on a flat 4 mile rail trail loop in Poland, Maine, where participants run as many loops as they wish and recorded mileage is recognized; shirts included with paid entry.

A timed 5K loop through woods and fields at the Maine Outdoor Wellness Center on June 20, 2026. Bibs, water, snacks, and family activities are provided and a $15 registration supports community building and programming.

Field & Forest 5 Miler is a roughly 5 mile trail race on the Crystal Spring property in Brunswick, ME. The mostly off pavement course has single track and wood bridges, and the field is limited to 50 runners.

A trail 5 km race at Libby Hill Forest Trails in Gray, ME on June 21, 2026. Online registration is $15 through June 19, race day registration is $20 and students enter free. Proceeds support trail maintenance and door prize drawings are pla..

A community trail event in Freeport, Maine on June 21, 2026 featuring a 5K loop through the school property plus a one mile kids run, part of Faith Fest with free registration from May 20 to June 21.

A small weeknight trail race series around Portland Maine from June 25 to July 30 2026, featuring races of about 5K to 6.5 miles, capped fields, partnerships with local land trusts, and series prizes for those who complete three races.

A single-day endurance walk on Cranmore Mountain with looped distances from 7 to 28 miles, optional weighted rucking, timed tracking, aid stations, and mountain views over North Conway and the White Mountains.

A charity team challenge on June 27, 2026 in Bristol, NH that recreates Special Forces mission tasks. Teams of 6–12 choose Operator or Recruit levels, with awards for top teams, MVPs, fundraising leaders, and participant milestones.

Second annual Kennebec Savings Bank East Bayside Trail Fest in Portland on June 28 2026 offers three trail events plus a post event celebration with music, food trucks and local beer. Proceeds support Portland Trails and the Bicycle Coaliti..

A women only 5K obstacle mud run with 18+ obstacles at Hemond's MX & Offroad Park in Minot, Maine on June 28, 2026. Open to females aged seven and up who may run, jog, or walk the course.

A roughly 4.5 mile trail run in Webb Forest near Sunapee, New Hampshire on June 28, 2026, benefiting the Sunapee Middle High School Track and Field program. The course features mountain vistas, single track and varied terrain, with raffle p..

A Fourth of July run/walk in Newport and Derby, VT, on gravel paths and wooded trails with distances from 2 miles to a half marathon; a portion of fees supports NAMI Vermont and ice cream follows the event.

A family oriented 5k on July 4 in Tamworth that begins at historic Ordination Rock, tours village streets and museum trails, includes a bandana, ice cream and a bib raffle, and supports the Tamworth Outing Club.

A backyard ultra on Portland's Back Cove Trail featuring repeated 4.16 mile loops along a tidal estuary. Two aid stations, on site personnel, free adjacent parking, and volunteer support are provided; refunds are restricted.

A looped trail ultramarathon in Northfield, NH on July 11, 2026, the Spaulding Woods 50K runs five 10K singletrack loops with aid stations, a ten hour finish limit, and an eight hour cutoff to start the final loop.

The 46th annual Bear Swamp Run is held July 11, 2026 in Middlesex, Vermont, featuring a 5.7 miles course from Rumney Memorial School. Age-group and gender divisions are included, with awards for overall and age-category top finishers.