Trail Running calendar near Bridgewater 2026-2027

An 18 mile out and back trail run from Windblown Ski Area toward Watatic Mountain Reservation, featuring steep, technical single track and uneven terrain. Prior trail running experience is strongly recommended.

TAM Trek is a trail race and fun run in Middlebury, Vermont supporting the Trail Around Middlebury. Events range from a full 19 mile route around the village to shorter trail races and a family friendly two mile run.

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.

Pair up for a three hour endurance relay on a two mile loop of trails and fields. Alternate laps with your partner to accumulate the maximum distance possible in this team based challenge.

A community 5K in Hillsborough, NH on September 20, 2026, organized by the Hillsboro Fire Department. The off-road course may be uneven and strollers are not recommended; registration runs March 25 to September 19 with a $30 fee.

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..

An 8.5 mile trail loop at Merck Forest in Rupert, Vermont with about 1,800 ft of climbing, two aid stations, and a separate 0.75 mile kids loop. Field limits apply and all proceeds support Merck Forest & Farmland Center.

Trail races on maintained local trails in Arundel, ME offering 5k, 10k and half marathon options, plus a kid's bike race, participant medals and shirts, live music and food.

A multisport festival at Pawtuckaway State Park offering swim, bike and run options for people who identify as women. Choose an individual triathlon, two sport combo, single sport or a relay team in a non competitive setting.

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.

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 on September 27, 2026 featuring steep ridge climbs, technical single track, one aid station, mandatory mountain gear checks, and postrace food and beer for ages 21 and over.

Run for Nature in Lowell on September 27, 2026 features a 10K trail run, a 5K run or walk and a kids one mile fun run, with marked trails and community activities supporting local conservation and education.

Trail races in Northfield, Vermont centered at the Norwich Shaw Outdoor Center, featuring a 7.5 mile summit race, an Anchor Challenge 6k, and free youth races. The event raises funds for the Northfield Town Forest and the Norwich cross coun..

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 community event in Gilford, New Hampshire on October 4, 2026, with categories for adults, youth, and children and a complimentary shirt for those who register before September 16.