Trail Running calendar near Moosup 2025-2026

Goodwin Trail Challenge (October 12, 2025) The Goodwin Trail Challenge is a registered mountain bike event held on October 12, 2025. Registration is required through BikeReg and includes a donation to East Haddam Land Trust that provides a..

Join the Helping Hands of EG 5K, a scenic charity trail run in East Greenwich supporting Spaulding Rehab and Journey Forward. Honor a local athlete and enjoy a family friendly course with shirts and awards.

Run scenic trails at Weir River Farm and nearby woods in a welcoming community trail race with distances for all levels. Enjoy post race treats and family farm fun while supporting the farm.

Take on the rugged Bimblers Bluff 50K in Guilford Connecticut on October 19, 2025. Enjoy a challenging off road course through scenic woodlands and rocky single track while supporting local land conservation.

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.

Cheshire Community YMCA 5K Harvest Trail Run in Cheshire, CT, is a race around Ives Farm. The all-ages event winds through fields and trails on the farm, starting and finishing at the remodeled barn. Proceeds support the YMCA’s Cheshire com..

Explore scenic single track at Grills Preserve in the WTAC Fall Trail Race Series with 10 Mile and 10K options. Enjoy riverfront views, bridges, and post race pizza in a friendly community trail event.

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..

RACE FOR THE GREENWAY 5K RUN / WALK takes place at Hallock State Park in Riverhead, NY. The mostly flat off-road 5K course weaves through parkland with views of beaches, vineyards, ponds, and forests, featuring loose gravel and grass underf..

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..

Run through the vines at Stonington Vineyards in this chip timed 5k that finishes with a wine pour, unique finisher medal, and a shatterproof wine glass. Two laps through scenic vineyard trails make it perfect for runners and walkers.

Run or stroll through historic Alice Newton Street Park at the Woodbridge Trail Run plus Woodland Walk, with a challenging two loop 4 mile course and an easy 2 mile walk to the falls. Participants receive custom tech T shirts and post event..

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.

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.

Located in Brookhaven State Park, Wading River, NY, the Brookhaven Trail Half Marathon and 5 Mile offer two trail-running distances. The course traverses a mix of Suffolk County woodlands, including single-track, fire roads, sandy sections,..