Trail Running calendar near Winchester 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.

Join Run for the Hills on October 26, 2025 in Harvard, Massachusetts for a scenic off road 5K through orchards, woods and fields plus a 1 mile kids fun run. Enjoy post race refreshments and support the Harvard Conservation Trust.

Hit the trails at Powisset Farm on October 26 for a family friendly fall race with distances from 1.5 to 8.3 miles through Powisset and Noanet Woodlands. Enjoy cider donuts, post race food, kids activities, and scenic singletrack.

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..

Join the Holistic Hustle 5K and 10K at Emmons Preserve on Nov 1 for scenic runs and a kids fun run. Earn a wood burned finisher medal, enjoy music, games and treats, and enter a raffle supporting School Around Us.

The Hugs from Vets Trail will take place in Henniker on Sunday 2 November 2025. You can run 10 kilometers.

Run the 21st annual GFRC Busa Bushwhack Trail Races in Framingham on Nov 2, with 5.3 mile and 10 mile courses through scenic, technical trails in Callahan State Park. Enjoy indoor facilities, mile markers, a finisher gift and log trophies.

Tackle the Fall Trailblazer Ultra at White Barn Farm in Wrentham with 12, 24 or 36 miles of rugged single track through conservation land and features like Knuck Up Hill and Pinnacle Rock. Cupless event so bring your own water.

Push your limits at Race for DFL, a backyard ultra at Kenty's Farm in Winchendon MA where runners repeat 4.1666 mile laps until only one remains. Choose 6, 12 or 24 hour options and enjoy themed laps, fun gear and great camaraderie.

Join the Centerville Bank Thompson Turkey Trot at West Thompson Dam for a cross country 5 km, a relaxed 3 km Wobble walk and a kids fun run. Wear Thanksgiving or turkey gear and help support local trails, parks and the TEEG food pantry.

Tackle technical, hilly single track in Upton State Forest on November 9, 2025 at the Upton 10.5K and Half Marathon. Pick a challenging 10.5K or two lap half marathon and warm up after with soup, fire pits and swag.

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..

Run scenic trails around Watchaug Pond at Burlingame State Park with 8 mile and 4 mile options in the Lil Rhody Runaround. Close out the WTAC Fall Race Series while soaking up classic New England fall scenery.

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.

Run a scenic 4 mile through Mine Falls Park in Nashua and celebrate afterward with a lively post race party and raffle at Martha's Exchange & Brewery. All proceeds support the Nashua Children's Home, so every step helps a great cause.

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.