Trail Running calendar near Drakes Island Beach 2026-2027

Big Brad Ultras at Bradbury Mountain State Park offers 25K and 50K options on a 15.5-mile single-track loop with technical, hilly terrain, significant elevation gain, aid stations, and drop-bag access.

A community 5K trail run and walk at Skyline Farm on Sunday, September 13, 2026, across fields, hills and woods. The day includes a free kids' 1K fun run, post-event food and music, and prizes for individual and team finishers.

GBTC XC Invite in Carlisle, MA features youth and Open/Masters cross-country races at Great Brook Farm State Park on September 13, 2026. Distances include a 2K youth race and multiple 5K races; registration runs August 1 to September 11.

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 trail-based 5K run/walk and a 3K walking route at Mine Falls Park supporting Meals on Wheels of Hillsborough County, with a $30 registration and a 2026 event T-shirt for early registrants.

An 18 mile out and back trail race in New Ipswich, New Hampshire, climbing toward Watatic Mountain Reservation with technical, rugged single-track terrain. Registration opens June 15 2026 and the fee is $55.

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..

The Arc'teryx Run Boston will take place in Milton on Sunday 20 September 2026. You can run 10 kilometers.

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 at Wasserman Park on September 26, 2026, featuring 12+ beginner to intermediate obstacles. Entry is limited to 200 participants, costs $40, and early registrants receive a race shirt and finisher medal.

A trail ultramarathon on September 27, 2026 in Freeport ME using a roughly 5 mile loop repeated for 10, 6, or 2 laps. The route is all dirt trails with bridges, stairs, and roots and has a single aid area at the start and finish.

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 at the Assabet River National Wildlife Refuge in Sudbury MA include a 10K, a 30K and a 6 hour timed event. The course uses dirt and gravel double track trails with two aid stations and cupless fueling.

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.

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.