Trail Running calendar near Gloucester 2025-2026

Stairs4RTroops 2025 at Gillette Stadium in Foxboro, Massachusetts is a stair climb, walk, or run up the stadium stairs and around the lower concourses. Held on October 5, 2025, the event features multiple waves roughly every 15 to 30 minutes, including a special Firefighter Wave. The first 2,000 reg..

Midstate Massive Ultra Trail is a UTMB Index endurance race held October 11–12, 2025, spanning New Ipswich, NH, and central Massachusetts with border crossings into New Hampshire and Rhode Island. Runners choose from three point-to-point options—100 miles, 50 miles, and 50 kilometers—following the A..

The Wayland / HFC Striders XC Festival, held in Wayland, Massachusetts, is a vibrant cross-country running event featuring three youth 3K races and two open 5K races for adults. The course winds through scenic fields and wooded trails, offering a challenging and enjoyable experience for runners of a..

Vulcan's Fury Trail Race in Nottingham, New Hampshire offers two rugged courses—the Half Marathon and the 5 Miler—set on hiking trails through a once volcanic landscape at Pawtuck. The course is described as technical and scenic, featuring a massive boulder field, dense forest, single-track switchba..

The Ghost Train Trail Races, held in Brookline, New Hampshire, are a series of trail running events along the historic Granite Town Rail Trail. This mostly flat, well-groomed course follows an old railroad bed used in the late 19th and early 20th centuries, featuring a mix of dirt and about one mile..

United We Move Trailfest, held annually in Fall River, MA, takes place in the scenic Fall River Bioreserve. Participants can choose to walk, run, or ride on various courses: a 1.1-mile Tattapanum Trail or 5K walk; 5K or 10-mile runs on mixed terrain including paved, dirt, and grassy trails; and 10 o..

Located on Mansfield's WWII Veterans Memorial Trail in Massachusetts, the WWII Veterans Memorial Trail Weighted Race is a 2.5-mile out-and-back loop on a rail trail with paved, gravel, and grass sections. In this 6-hour timed event, participants carry weight per lap, with their lap distance multipli..

The Weir River Farm Trail Race, held annually in Hingham, Massachusetts, offers runners three trail distances: 10 miles, 6 miles, and 3.4 miles. The race courses wind through the scenic trails of Weir River Farm, Whitney, and Thayer Woods, with the 10-mile route including additional loops in Wompatu..

The Ravenswood Trail Race will take place in Gloucester on Sunday 19 October 2025. You can run between 4 and 4 miles.

Womp Romp Trail Race is held in Hingham, Massachusetts at Wompatuck State Park (South Field). It offers a 50K (three loops plus a mile) and a single-loop 10-mile option. The course blends single-track, wide trails, and some pavement, with about two miles of pavement per loop.It’s a cupless race, so..

Pumpkin Pacer 5k @ White Barn Farm is a 5K off-road trail run/walk held at White Barn Farm, 431 South Street, Wrentham, MA 02093. It’s the final race in the Farm To Trail 5K Series and is open to all ages and abilities. The course weaves through scenic conservation land and farm property, featuring..

Powisset Farm Trail Run - Fall is a Barn to Run Trail Race Series event held at Powisset Farm in Dover, MA, on October 26, 2025. The course spans Powisset Farm and adjacent Noanet Woodlands, with four distance choices: 8.3, 5.6, 3.1, and 1.5 miles. The atmosphere blends competitive trail running wit..

New Boston, NH hosts The Hamsterwheel, an 11th-year ultrarun along the New Boston Rail Trail by the Piscataquog River. The course is a continuous 4.0-mile loop that is largely flat with one minor speed bump, starting near the Hillsborough County Fairground and turning at Lang’s Station. Runners may..

The TARC Stone Cat Trail Festival will take place in Ipswich on Saturday 1 November 2025. You can run between 10 and 100 kilometers.

The Holistic Hustle 5K/10K is an annual running event held at the scenic Emmons Preserve in Kennebunkport, Maine. The 4th edition, scheduled for November 1, 2025, features timed 5K and 10K run/walk races alongside a kids' half-mile fun run for participants aged 13 and under. The event offers a livel..

The Hugs from Vets Trail will take place in Henniker on Sunday 2 November 2025. You can run 10 kilometers.

Race for DFL is a last-runner-standing backyard ultra held at Kenty’s Farm in Winchendon, Massachusetts. The event uses a single lap of about 4.17 miles, with a course mixture of grassy field, forest trail, crushed gravel bike path, and a dirt road, totaling around 150 feet of elevation gain per lap..

The Centerville Bank Thompson Turkey Trot is an annual event held at the West Thompson Dam Overlook Shelter in Thompson, Connecticut. It features a 5K timed trail run, a 3K untimed walk called the "Wobble" where dogs on leashes are welcome, and a free kids' fun run for children 12 and under. The eve..

Set in Upton State Forest in Upton, MA, the Upton 10.5K and Half Marathon Trail Race offers two distances: a 10.5K trail run and a 21K half marathon, run as two laps. The course features technical, hilly single-track trails and forest roads, with about 720 feet of elevation gain per lap. Aid station..

The Tarckey Trot 6 Hour - Winchester, MA will take place in Winchester on Saturday 15 November 2025. You can run between 6 and 6 kilometers.