Trail Running calendar near Gilford 2026-2027

A traditional up and down mountain race in Waterville Valley, NH on September 20, 2026 covering about 7 miles with 3000 feet of ascent; youth entry is available and day of registration is offered.

Trail races on the ACT Multi-Purpose Trail and Eastern Trail in Arundel with 5k, 10k, half marathon and a free kids bike race, plus medals, shirts, live music and food.

An inclusive multisport festival at Pawtuckaway State Park on 09/26/2026 offering a 0.4 mile swim, 5.5 mile trail bike and 3 mile run in single sport, two sport, relay or full triathlon formats. No chip timing; safety gear is required.

A trail based 5K obstacle course race at Wasserman Park on September 26, 2026, featuring 12 or more beginner to intermediate obstacles. Entry is limited to 200 participants and the fee is $40.

A trail event at Ascutney Outdoors offering 50 mile and 50K ultra runs, team relays, mountain bike races and kids fun races. Proceeds support Vermont Adaptive and registration details are published for the 2026 race weekend.

A looped trail ultra at Wolfe's Neck Farm on dirt roads and conservation trails, featuring 5-mile loops with bridges, stairs, and about 570 ft gain per loop; distances include 50, 30, and 10 miles plus relays.

A 21k trail race at Pleasant Mountain in Bridgton, ME, featuring steep ridge climbs, technical single-track, one aid station, and an afterparty with food, live music, and beer for attendees 21 and older.

A community run at Shedd Park featuring a 5K, a 10K trail run, and a 1-mile kids fun run, with educational displays and proceeds supporting LP&CT's conservation and education programs.

The 4th annual Paine Mountain races in Northfield Vermont on September 27, 2026 include the Anchor Challenge 6k, a 7.5 mile summit race and free youth races. Proceeds benefit the Northfield Town Forest and Norwich cross country program.

A last person standing trail event in Center Conway, New Hampshire on October 3, 2026. Runners repeat a roughly 3.5 mile forest loop with minimal aid, camping options, food and event swag.

A 25 kilometer trail race through the Edwin L. Smith Preserve in Kennebunkport, Maine on October 3, 2026. Proceeds support the Kennebunkport Conservation Trust and registration is limited to 100 entrants.

Trail races in Groton, Massachusetts on October 4, 2026, organized by local running and trails groups. Two distances, 9.5 miles and 3.4 miles, total entries limited to 250, online registration closes October 3.

Keene Family YMCA Fall Foliage Trail Races feature 5K and 10K trail courses starting and finishing at the Keene YMCA, with chip timing, age-group prizes, and proceeds supporting YMCA programs and access.

A one-mile charity run at Gunstock Mountain Resort on October 4, 2026, benefiting Big Brothers Big Sisters of New Hampshire & Vermont. Online registration closes October 2; adult and teen entries are $20, children under 12 enter free.

A 5K trail race and 1-mile fun run at Tibbetts Field in Madbury, NH on October 4, 2026, featuring a 2-mile loop through Powder Major Forest over natural terrain. A portion of proceeds will support a local family in need.

Experience the peak of New England autumn on a journey through the mountains and fields of central Massachusetts. This trail event offers three distances crossing state borders for runners seeking adventure on the Midstate Trail.

Devil's Den Ultra is a trail event on Wright's Mountain in Bradford, VT on October 10 and 11, 2026. Runners complete laps of a 10K loop on mixed rocky and rooty terrain, with a 100 runner cap and themed tarot awards.

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 rugged trail race at Pawtuckaway State Park featuring technical terrain, boulders, streams and a rocky climb. It offers a half marathon and a 5 mile option and lists $7500 in prize money for 2026.

A mixed 100k event near Virgil Parris Preserve combining about 25k running and 75k cycling across six trail parcels, cupless aid stations, and beneficiary support for local land trust and youth nonprofit.