Trail Running calendar near Plymouth 2026-2027

Mountain bike and ultra-run event at Ascutney Outdoors near West Windsor VT with 50 mile and 50K options, relays and kids races, benefits Vermont Adaptive.

Bike, run, or walk on the Lamoille Valley Rail Trail in Morrisville, Vermont. Proceeds support services for healthy aging in Central Vermont including groceries, emergency fuel, prescription assistance, and exercise classes.

A 21k trail race on Pleasant Mountain in Bridgton, ME, featuring steep ridge climbs, technical single-track, one aid station, and a finish-area afterparty with food and beer.

Trail races at Paine Mountain in Northfield VT featuring a 7.5 mile summit course, a 6K Anchor route, and free youth races supporting local trail management and XC programs.

Last person standing trail ultra in Center Conway, NH on a 3.5 mile forest loop with camping, meals, swag and a beer mile the following day.

A 25K trail race at Edwin L. Smith Preserve in Kennebunkport, ME on October 3, 2026, with proceeds benefiting the Kennebunkport Conservation Trust and registration capped at 100.

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.

Trail running at Tibbetts Field in Madbury includes a 5K and a 1 mile fun run over natural terrain through Powder Major Forest, with proceeds supporting youth recreation scholarships.

Trail 5k in Oxford, Maine starting and ending at Oxbow Beer Garden to benefit Mission Working Dogs; properly trained service dogs only and beer tickets for those 21 or older.

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.

Trail event in Bradford Vermont with looped mountain course, 30 hour, 12 hour and 6 mile options, tarot themed awards and a 100 runner cap.

A community run on October 10, 2026, organized by the Lebanon Recreation, Arts, and Parks Department, following the Rail Trail from Enfield along Mascoma Lake and the Mascoma River to a finish in Lebanon. Fees change before race week and pa..

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 fully human powered 100K in Norway, Maine mixing 25k of trail running and 75k of cycling across six preserves, offered as solo and duo with charitable beneficiaries.

Trail marathon and half marathon at Trapp Family Lodge in Stowe, VT on October 17, 2026, run on a 13.1 mile loop with steep climbs and single track.

Trail event in Brookline, NH with multiple races on the Granite Town Rail Trail and proceeds supporting local conservation.

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.

Trail running event in Windham, ME offering a 50k of five 6.5 mile loops and a single-loop 10k with aid stations and volunteer support.