Trail Running calendar near Holliston 2026-2027

A choose your own adventure trail event at Chesterfield Gorge Reservation on a rolling jeep road alongside the river. Multiple ultra and shorter distances are offered, with a 30 hour window for ultras, water and manned aid stations, and non..

A scenic 2.5 mile off-road run or walk around Horn Pond paired with a festival at Ice House Park featuring food trucks, a DJ, raffles, kids activities, and over 25 local mental health and substance use providers.

A themed Monday night in the Mine Falls Summer Trail Series at Stellos Stadium, featuring 5K and 5 mile options, music, giveaways and both in person and flexible virtual participation.

Point to point trail ultramarathon along the New England Trail with 112 mile and 50 mile options through Connecticut. Entrants must donate to the Connecticut Forest and Park Association and arrange their own crew and navigation support.

Run a flat, out-and-back course on the scenic Holliston Rail Trail. This event offers a 5K and a 10K for adults, plus a fun run for kids with distances based on age. The community gathering point is Blair Square in Holliston.

A timed 20 mile hiking event on June 6, 2026 at Wompatuck State Park in Hingham, MA, set in 3,500 acres of wooded trails. The event is sold out and a wait list is maintained for openings.

Enjoy a 3 mile trail run through the scenic Westport Rivers Vineyard & Winery followed by a vineyard celebration with dinner, wine, and live music.

A community event at Stanley Park on June 7, 2026 featuring a 5K trail run or a one mile accessible route. Proceeds support renal medullary carcinoma awareness and related programs.

A 5.4 mile trail race through Dogtown in Rockport and Gloucester, MA featuring varied terrain and named historic trails. Runners and walkers are welcome; early registrants receive T-shirts and prizes are awarded by overall and age categorie..

A five mile fun run along the Cheshire Rail Trail from the Fitzwilliam Railroad Depot to the restored Troy Depot, with a short children's loop and food and festivities at both depots. The event raises funds for local historical societies.

Experience a scenic New England trail event in Dunstable with a 5 mile loop or a 6 hour timed challenge. Support the Humane Society while running through historic quarries and former ski hills.

Trail race options of 50k, 30k and 10k around Edge Hill Conservation Area in Ashfield Massachusetts, run on single track and dirt roads. The event partners with Franklin Land Trust and supports habitat restoration and land conservation.

A Last Human Standing trail race near Big River Management Area in West Greenwich, RI. Runners repeat the same loop each hour and must complete each lap within 60 minutes to remain in the field until only one athlete remains.

Trail races at Mansfield Hollow State Park include a roughly 15.7 mile out and back on the Nipmuck Trail and a new 5K single track loop; proceeds benefit Connecticut trail stewardship and the event is organized by the Shenipsit Striders.

Celebrate the switch to summer with a trail race through the landscape of Hebron Connecticut. Choose between three different distances for a run through the woods during the solstice.

Run a scenic yet rugged half marathon trail race at Lynn Woods Reservation in Massachusetts. This 13.1-mile event features three challenging loops showcasing the historic Stone Tower. The focus is on sustainability and a centralized start/f..

Experience a 5k obstacle mud run designed for unity and women empowerment at Kimball Farm in Haverhill. Join a supportive community for a day of teamwork and mud while supporting the National Breast Cancer Foundation.

A three-race summer trail series at West Hill Dam featuring well-marked wooded single and double-track trails, limited fields, age-group prizes, and a portion of fees donated to local food pantries.

A Spartan obstacle race weekend at Carter & Stevens Farm in Barre, MA, featuring a Sprint 5 km with 20 obstacles, a Super 10 km with 25 obstacles, and kids races. The farm venue includes mud, woods, rolling hills and a farm store.

A point to point 5K in East Hampton beginning at the Connecticut Draft Horse Rescue with shuttle transport from Center School. Bib pick-up is at Center School gym and awards are presented by age group after the race.