Trail Running calendar near Winchendon 2026-2027

A five mile fun run along the Cheshire Rail Trail from Fitzwilliam Depot to the restored Troy Depot on June 13, 2026. The day features food and festivities, a children's loop, return transport on request, and benefits local historical socie..

Experience a day of trail running and mountain biking at the Norbrook Farm Brewery Trail Festival. Enjoy multiple race distances, local food trucks, and rewards at this scenic Connecticut brewery.

A second annual trail event in Dunstable, Massachusetts offering a 5 mile loop or a six hour race of repeated 5 mile loops. The course follows an old railroad bed, an arched stone bridge, woods, peaks, and single track trails.

A trail event in Ashfield MA on June 13 2026 offering 50k, 30k and 10k courses across single track, dirt roads, and former golf course terrain. Aid stations, basic race food, and first aid are provided; proceeds support local land conservat..

A loop based endurance race near Big River Management Area in West Greenwich, RI where runners must complete each circuit within 60 minutes to continue; laps repeat at one hour intervals until only one runner remains.

A trail race in the Newport town forest with 6- and 3-mile options on rocky, rooty, hilly singletrack. Starts and finishes at Newport High School; proceeds support local recreation and town forest trails.

A trail 5K and 10K at Pleasant Valley Wildlife Sanctuary on June 13, 2026, with routes on single track trails and carriage roads. Proceeds support Mass Audubon conservation; water stations, finish area refreshments, and limited parking.

A mixed-surface 5 km race and one-mile fun run at Hampshire Regional High School in Westhampton on June 13, 2026. The 5 km combines paved roads and wooded trails; awards, refreshments, restrooms and parking are provided.

A community fun run on 06/13/2026 behind Madbury Town Hall with a 1K kids run and a 5K route through Kingman Farm trails. Registration is free and donations for park improvements are accepted on the day.

Trail races at Mansfield Hollow State Park with a 15-mile out-and-back on the Nipmuck Trail and a new 5K route; proceeds support Connecticut trail stewardship and the event is organized by Shenipsit Striders.

A family-friendly three-loop course of about 5 km through Natick Community Organic Farm with mixed trail, field and road surfaces. All participants receive a chicken medal and proceeds support the farm’s education and teen programs.

A 5.6 K trail run and walk at Berry Pond in Harold Parker State Forest on June 14, 2026. Walkers and leashed dogs are welcome; prizes are awarded, all entrants receive a bandana, and hotdogs are provided after the race.

Teams are driven blindfolded several miles to an unknown location, then must navigate back to the start by the shortest route. This free team event uses cross country scoring and prohibits GPS, phones, and running on I 95 or I 495.

A morning trail run at Gay City State Park on June 20, 2026, offering 8 mile, 5 mile and 3 mile races. The 8 mile joins regional trail series and includes team competition with prize money.

A trail race at the Dublin School Outdoor Center on June 20, 2026 offering a 10K and a half marathon with significant elevation gain, rugged terrain, and views of Mount Monadnock.

A 5K through Camp Jewell’s roads and wooded trails including a covered bridge, plus a free one mile kids run. Pre entry is $30 before June 6 and increases to $35 afterward.

A trail half marathon in Lynn Woods Reservation on June 21, 2026, run as three identical loops over forested singletrack and carriage roads. The event emphasizes environmental stewardship and uses a centralized start and finish at the main..

A women only 5K obstacle mud run at Kimball Farm in Haverhill, MA on June 21, 2026. The course features 18 plus obstacles and welcomes participants age 7 and up with an emphasis on fun and teamwork rather than competition.

TSR Trail Race is a loop-format trail run on June 21, 2026, in Adams, MA, featuring hand and machine built singletrack with climbs, descents, and a gravel meadow loop; proceeds support Thunderbolt Ski Runners' trail stewardship.

Three summer trail races at West Hill Dam in Uxbridge, MA, with well-marked wooded single and double-track courses, limited fields, age-group prizes, and a portion of fees donated to local food pantries.