Trail Running calendar near Ashford 2026-2027

An inclusive trail festival at Northfield Mountain on August 29, 2026 that centers queer and trans runners and allies. It offers a 20k prediction race, an untimed 5k fun run or hike, and a Kid's Run with community-focused prizes.

Timed loop trails on Wachusett Mountain with 7, 14, 21, and 28 mile options over ski slopes and single-track. Participants have 10 hours to finish, with weighted vest options and marked courses; finishers receive a shirt and patch.

Experience a scenic 3.3 mile trail run or hike through the Oswegatchie Hills Nature Preserve. Support local land conservation while enjoying a timed course around Clark Pond followed by an awards ceremony with refreshments.

Trail Animals Running Club hosts a multi distance trail event at Great Brook Farm State Park on September 5, 2026. Looped 10K and 10 mile courses cover distances from 10K to 50 miles, plus a youth fun run and a Yeti Mischief Mile.

A community 5K run and walk in Nashua, NH on September 5, 2026 with free registration for veterans and children, a fee for participants 13 and older, event shirts, donation options and volunteer opportunities. Use #nashua5k for photos.

A family friendly beach 5k obstacle race in Stratford each September, featuring 18 plus obstacles and community fundraising for Sterling Community Center programs. Participants and teams raise funds while running, walking, or navigating obs..

A group run along the Farmington Canal Heritage Trail covering roughly 56 miles from West Suffield to New Haven, held as a fundraiser for Mental Health Connecticut. The event is largely self supported with basic volunteer aid stations and a..

A Keene State College alumni cross-country meet on 09/12/2026 at the Keene State Athletic Complex featuring a men's 5K and a women's 2 Mile race; registration runs 09/06 to 09/12 with a $25 fee per event.

A trail race day at Pittsfield State Forest with 50k, 25k, 15k and a new 5 mile option, a double-loop course with three aid stations and charity fundraising through BURCS and Free to Run.

Experience the rugged beauty of northwest Connecticut at Macedonia Brook State Park. Featuring single track trails and views of the Catskill Mountains, this event offers 12K, 25K, and 50K distances for trail runners.

Pisgah Mountain Trail Races in Chesterfield, NH offers 50k and 23k mountain trail ultraruns on Sunday 9/13/26. Aid stations provide LMNT, Tailwinds, and Untapped and proceeds support New Hampshire Special Olympics.

A USATF New England Cross Country Grand Prix meet at Great Brook Farm Ski Touring Center in Carlisle, MA on September 13, 2026, featuring a youth 2K and several 5K races across open and masters categories.

A free 3 mile out-and-back beach run at Westerly Town Beach held at low tide. The community event is organized by the Westerly Track Club and the Stavros family as a memorial run.

A multi-race trail festival at Lakeside Park in Pawling, NY offering timed 24, 12 day, 12 night, 6 and 3 hour events on an about 1.68 mile loop with on-course aid, music, and finisher medals.

A community fundraiser in Pomfret Center with a trail 5K and a 0.5 mile kids run supporting the Pomfret Community School PTO. Early and later registration fees differ and awards plus finisher medals are given.

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.

A one mile obstacle course in Warren, RI with two giant mud pits, kids play area, food and giveaways. Proceeds support Thrive Outside and its programs to expand youth access to nature.

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.

A 5K trail run at Winding Trails in Farmington on the designated course around Walton Pond, with registration from February 20 to September 20 and a $35 fee; overall and age-group awards plus a prize for the first local finishers.

Experience the technical terrain of Cockaponsett State Forest with 4 and 9 mile trail races. Navigate hills and rocky paths in Chester to support PanCAN and the Blue Blazed Trail Race series.