Trail Running calendar near Deering 2025-2026

Carry your chosen load and tackle the 2.5 mile out and back on the WWII Veterans Memorial Trail in Mansfield, aiming to complete as many laps as you can in a six hour window. Each lap adds to your pound mile score for overall placement.

Soak up autumn on rugged single track at Mt Tom State Park with options from a 5k fun run to a 25k solo or two person relay. This nonprofit fundraiser supports Kestrel Land Trust and serves up aid stations, prizes and a trail challenge.

Run the historic Ghost Train Rail Trail along a mostly flat, well groomed old railroad bed in Brookline and Milford, New Hampshire. Choose from a 30 hour ultramarathon, relays, or shorter distances while supporting local conservation.

The Ravenswood Trail Race, part of the North Shore Trail Series, takes place in Ravenswood Park, featuring a scenic course through single track and carriage roads amid peak fall foliage. This classic fall trail race offers a challenging and..

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,..

Book It for Books 5k & 10k is a charity running event at Lake Accotink Park in Springfield, VA, benefiting Reading is Fundamental of Northern Virginia (RIF NOVA). The weekend features a 1-mile fun run, a 5k trail out-and-back on the lake’s..

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 th..

Enjoy crisp fall trails at the Powisset Farm Trail Run in Dover on October 26, 2025, with distances from 1.5 to 8.3 miles through Powisset Farm and Noanet Woodlands. Family friendly fun, cider donuts and post race food make it a great autum..

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‑m..

Join The Hamsterwheel in New Boston NH for a friendly 4 mile loop ultrarun with 6, 12, 24 and 30 hour solo and relay options. Scenic rail trail, night running, team camaraderie and quirky buckles make it a fun intro or a bold challenge.

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..

Run into the night at Cranmore Resort with a fun 5K or 10K mountain race under LED lanterns and reflective flags. Headlamps required, postrace pizza and apres create the perfect evening of trail racing and celebration.

The TARC Stone Cat Trail Festival is a renowned trail running event held annually in Ipswich, Massachusetts, within Willowdale State Forest. Offering a variety of distances including 10K, half marathon, marathon, 50-mile, and 100K races, pl..

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 d..

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,..

Take on scenic but technical, hilly single track trails in Upton State Forest with 10.5K or 21K (two laps) options on Sunday November 9, 2025. Field is limited to 250 runners and online pre registration closes November 7.

Join the TARCkey Trot, a six hour timed challenge at Wright Locke Farm on November 15, 2025, running multiple 5K trail loops over rocky rollers. Tackle as many laps as you like while supporting land conservation.

Windham Woods School Thankful Trails 5K Run & Walk Windham Woods School hosts the 2nd annual Thankful Trails event on November 15, 2025, at 39 Roulston Road, Windham, NH. The event includes a 5K trail run/walk and a Kids Fun Run for chi..

Mount Ascutney Vertical Backyard : Nov 22, 2025, Brownsville, VT The event is a "Last Person Standing" format held at Mount Ascutney in Brownsville, VT (449 Ski Tow Rd). Participants complete repeated laps; each hour they must asc..