Trail Running calendar near Ashford 2025-2026

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 is a unique 6-hour timed running event set on a scenic 5K loop at Wright Locke Farm in Winchester, MA. Participants can run as many loops as they wish within the time limit, navigating a course filled with natural terrain challenges. The event promotes community engagement, offering..

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 Tarrywile Half Marathon, held at Tarrywile Park in Danbury, Connecticut, is a challenging trail race known for its significant elevation gain of nearly 3,000 feet and technical Northeast single-track terrain. The course offers stunning views of Danbury and the park's tranquil lakes. The event fe..

The Fall Fling will take place in Southington on Saturday 22 November 2025. You can run between 4 and 6 kilometers.

The Novemberfest Race is an annual 4-mile running event held in Nashua, New Hampshire, featuring a scenic course through Mine Falls Park. This community-focused race supports the Nashua Children's Home, with all proceeds benefiting the organization. The event also includes a raffle held at Martha's..

The Roxbury Thanksgiving Day Charity Race is a 5K event held annually in Roxbury, Connecticut. Scheduled for Thanksgiving Day, November 27, 2025, the race takes place at the Everett B. Hurlburt Community Park located at 18 Apple Lane.Participants run a 3.1-mile course, offering a community-focused a..

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 along the white-blazed Skyline Trail, featuring rugged terrain with roots, rocks, and elevation changes typical of New Engl..

The Tower Tag Challenge is a trail running event held at Sleeping Giant State Park in Hamden, Connecticut, known for its scenic views and historic Observation Tower. Participants run repeated loops of the Tower Trail, a 3.3 to 3.4-mile out-and-back course that ascends over 600 feet along a smooth ca..

The Frosty Forest 5K is a trail running event held in Roosevelt Forest, Stratford, Connecticut. This 5-kilometer race offers participants a chance to escape the roads and enjoy a scenic course through nature. Runners, joggers, hikers, and walkers are all welcome, with a requirement of some trail exp..

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..

The Sleeping Giant Trail Runs, held at Sleeping Giant State Park in Hamden, Connecticut, is a challenging trail running event known as one of the toughest in the Northeast. The race offers two distances: a 25K loop featuring over 3,000 feet of vertical gain, and a 50K option consisting of two loops...

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 Merrimack River Trail Race is a USATF-sanctioned 10-mile out-and-back trail run held in Andover, Massachusetts, starting from the DoubleTree by Hilton Hotel parking lot. The course features water stations at miles 2, 4, and 8, with a mix of unmanned and manned aid points. The event offers a frie..

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 Jack Bristol Lake Waramaug Ultra Races, held in Kent, Connecticut, is a historic ultra running event celebrating its 52nd anniversary in 2026. It features three race distances: 100K, 50 miles, and 50K, all conducted on primarily flat, rolling loops around scenic Lake Waramaug on paved roads. The..

The TARC Wapack and Back is a challenging trail running event held annually in Ashburnham, Massachusetts, along the scenic Wapack Trail. Offering three distance options—21.5 miles, 43 miles, and 50 miles—the race features rugged terrain with rocky ledges, boulder fields, granite slabs, and technical..