Trail Running calendar near Falmouth 2025-2026

The WWII Veterans Memorial Trail Weighted Race is a unique endurance event held in Mansfield, Massachusetts, on a 2.5-mile out-and-back rail trail featuring paved, gravel, and grass surfaces. Participants have six hours to complete as many laps as possible while carrying weighted packs, with their s..

The Weir River Farm Trail Race will take place in Hingham on Sunday 19 October 2025. You can run between 3 and 10 miles.

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 is an annual trail running event held at Wompatuck State Park in Hingham, Massachusetts, featuring a 10-mile loop race and a 50K race consisting of three loops plus an additional mile. The course offers a mix of single track, wide trails, and some paved sections, suitable for both novice a..

The Pumpkin Pacer 5k at White Barn Farm in Wrentham, Massachusetts, is a scenic trail run/walk/hike held annually in late October. This off-road 5K course features dirt and gravel paths with natural terrain including rocks, roots, and elevation changes, offering a fun challenge for all ages and skil..

The Powisset Farm Trail Run - Fall is a popular trail running event held at Powisset Farm in Dover, Massachusetts. Scheduled for October 26, 2025, it offers four race distances: 8.3, 5.6, 3.1, and 1.5 miles, traversing scenic trails through Powisset Farm and the neighboring Noanet Woodlands. The rac..

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 Stonington Vineyards Wine Run Turkey Trot 5k is a festive running event held at Stonington Vineyards in Stonington, Connecticut. This chip-timed 5k features a two-lap cross-country style course that winds through vineyard lanes, offering scenic views and some uneven terrain suitable for both run..

The Upton Half Marathon Trail Race, held in Upton State Forest, Massachusetts, offers a challenging and scenic trail running experience. Participants can choose between a 10.5K or a half marathon distance, with the half marathon consisting of two laps of a 6.5-mile course featuring technical, hilly..

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..

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 Li'l Rhody Runaround Trail Run will take place in Charlestown on Sunday 16 November 2025. You can run between 4 and 8 miles.

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..

The TARC Winter Classic is a trail running event held annually at Middlesex Fells Reservation in Stoneham, Massachusetts. It offers challenging distances of 8, 32, and 40 miles on the technical Skyline Trail, featuring roots, rocks, and elevation changes typical of New England terrain. Runners exper..

The Mount Hood Nutcracker Challenge will take place in Melrose on Saturday 13 December 2025. You can run 3 miles.

The TARCtic Frozen Yeti is a winter trail running event hosted by the Trail Animals Running Club at Hale Reservation in Westwood, Massachusetts. Scheduled for February 7-8, 2026, it offers two distance options: a 15-mile race and a challenging 30-hour ultra. The course features three roughly 5-mile..

Run Across CT is an ultramarathon event featuring a 123-mile point-to-point course across Connecticut, starting in East Thompson and finishing at the Wakeman Boys & Girls Club in Southport. The route traverses 25 towns and combines approximately 57 miles of well-maintained trails with scenic backroa..

The TARC Spring Classic is a trail running event held annually at Jericho Town Forest in Weston, Massachusetts. Offering 10K, Half Marathon, Marathon, and 50K distances, the course features a relatively flat, smooth 10K loop with twisting trails suitable for all skill levels. Runners complete multip..

The Wildcat 5K Trail Run-Walk-Wag is an annual event held in Boxford, Massachusetts, starting and finishing at the Danvers YMCA Camp overlooking scenic Stiles Pond. The race features separate courses for runners and walkers, including those with dogs ("waggers"), winding through the Wildcat State Fo..