Trail Running calendar near Buzzards Bay 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..

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..

The Tackle the Trail - Pomfret, CT will take place in Pomfret on Saturday 18 October 2025. You can run between 10 and 42 kilometers.

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.

The Grills Trail Run, hosted by the Westerly Track & Athletic Club, takes place at Grills Preserve in Westerly, Rhode Island. Scheduled for October 25, 2025, it features two race distances: a 10-mile and a 10K. Both courses start and finish at Grills Preserve, showcasing scenic trails with about 80%..

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..

Run for the Hills in Harvard, Massachusetts is a pair of off‑road trail races held at the Community Harvest Project Orchard (115 Prospect Hill Rd). The event features a challenging 5K trail run through orchard, woods, and fields, plus a 1‑mile kids’ fun run staying within orchard trails. The course..

Powisset Farm Trail Run - Fall invites runners to Powisset Farm in Dover, MA, for a scenic trek through Powisset Farm and nearby Noanet Woodlands. The event offers four distances—8.3, 5.6, 3.1 and 1.5 miles—catering to both experienced trail runners and newcomers. It’s part of the Barn to Run Trail..

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

Stonington Vineyards hosts the Wine Run Turkey Trot 5k at Stonington Vineyards in Stonington, CT. This timed 5k offers a run or walk on a two-lap cross-country course that begins and ends at the winery, weaving through vineyard lanes with occasional uneven footing. The atmosphere blends fitness with..

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..

Located in Upton State Forest, Upton, MA, the Upton 10.5K and Half Marathon Trail Race offers two trail options: a 10.5K and a half marathon run as two laps on technical, hilly single-track trails and forest roads. Each lap is about 6.5 miles with roughly 720 feet of elevation gain. The course featu..

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.

The Baystate Dirty Dog Trail Run-Ruck-Walk 5k is a rugged outdoor event held in Berkley, Massachusetts, honoring military personnel, first responders, and their K-9 partners. Participants can run, ruck with weighted packs, or walk a challenging 5k trail through scenic natural landscapes, often muddy..

Li'l Rhody Runaround Trail Run is held at Burlingame State Park in Charlestown, Rhode Island. It is the fourth and final race in WTAC’s Fall Trail Race Series, offering two trail distances: 8 miles and 4 miles on Watchaug Pond area trails. Expect a classic, wooded trail course around the pond, with..

TARC Winter Classic is a trail ultrarunning event at the Middlesex Fells Reservation in Stoneham, MA. Runners choose 8, 32, or 40 miles, starting and finishing at Fallon Road. The Skyline Trail offers a rugged New England course of roots, rocks, and elevation, with constant climbs and descents and o..