Trail Running calendar near Plymouth 2026-2027

A weekend of Spartan obstacle races at Killington Ski Resort in the Green Mountains, featuring Sprint, Beast, Ultra and a Kids Race across steep, off-trail terrain. The event listing includes obstacle counts, sample pricing, and participant..

A remote trail event on Kilkenny Ridge with 50 Mile, 25 Mile and 25K options along unmarked forest ridgelines. Navigation, mandatory safety gear and limited backcountry aid stations are required.

Experience the summit of Mount Agamenticus with a 5K or 1 mile trail race. Support local conservation efforts while running or hiking through Maine trails and participate in a raffle for all entrants.

A community 5K trail race in Hooksett that runs from Heads Pond trail through wooded conservation land to the Hooksett Public Library. A separate 0.5 mile kids fun run is available and proceeds support local youth programs.

A community 5K in Jaffrey, NH offering a woods trail and a rail trail out and back. Proceeds support the volunteer Jaffrey Firefighters Company and equipment needs of the Jaffrey Fire Department.

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..

A one day mountain trail challenge visiting five peaks around Westmore, Vermont, covering roughly 26 miles and about 6,142 feet of ascent. Staffed water and aid stations appear along the route and morning shuttles run from NorthWoods campus..

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.

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.