Trail Running calendar near Winchendon 2025-2026

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..

Womp Romp at Wompatuck State Park in Hingham MA offers 10 Mile and 50K trail courses across scenic single track with some muddy sections. Field is capped at 350 and proceeds benefit Friends of Wompatuck, Free to Run, and Footprints.

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 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..

Take on the Baystate Dirty Dog Trail Run Ruck Walk 5k in Berkley on November 16, a rugged, possibly muddy trail where you can run, ruck with a pack, walk, or bring a leashed dog. Proceeds support local beagle and K9 charities.

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..

Run the Novemberfest Race, a scenic 4 mile through Mine Falls Park in Nashua, finishing near the Millyard smokestack. Celebrate at Martha's Exchange after the race while supporting the Nashua Children’s Home.

Join a scenic road and rail trail run with prizes for top finishers. Route may change for weather and the event will be canceled if it snows. Entry is donation based; proceeds benefit a local dog rescue and community theater.

The Toonerville Trail Turkey Trot 5k will take place in Springfield on Thursday 27 November 2025. You can run 5 kilometers.

Turkeywacker 5K is a Thanksgiving morning trail run held in Wrentham, Massachusetts, at the William Rice Recreation Complex (54 Emerald Street). Now in its ninth year, the scenic 5K course winds through the complex’s trail system, welcoming..

Celebrate Thanksgiving on the trails at the F.I.T. Turkey Trot Trail Race in Cumberland, Rhode Island on November 27. Choose from 5K, 5 Mile, combo, multilap or a Kids Race and earn a unique finisher medal.