Trail Running calendar near Stonington 2025-2026

The Tackle the Trail - Pomfret, CT will take place in Pomfret on Saturday 18 October 2025. You can run between 10 and 42 kilometers.

Join United We Move at Fall River Bioreserve on Oct 18 for scenic runs, rides and walks across trails and gravel roads. Enjoy live music, family fun and a food and drink ticket included with registration.

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.

Tom Centinaro Memorial "Dam" Race is a 3.5-mile trail run/walk hosted by the Wolcott Lions Club in Wolcott, Connecticut. The race unfolds on the scenic, flat Mill Pond Trail at Woodtick Recreation, 201 Nichols Road. This community event ben..

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.

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.

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..

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 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.

Overview 8 Hours at the Farm is a timed trail running event presented by Steep Endurance on November 2 in Brookfield, Connecticut. The event is held at Gurski Farm / Williams Park with race headquarters and the start/finish located in the b..

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..

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.

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,..