Trail Running calendar near Stratford 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.

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..

Run a scenic off road 5K through meadows, ponds and wooded trails at the Hudson Highlands Nature Center in Cornwall, NY on October 18, 2025. Family friendly event benefits nature education and animal ambassadors; kids run free.

Join the Castle to River Run in Garrison, NY, with a half marathon, 5K and kids fun run raising funds for Friends of Philipstown Recreation. Tackle varied trail terrain, pick up a race shirt and enjoy community spirit.

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.

Experience peak fall foliage at Harriman State Park with Big Bear SquaTCh South, a rugged single loop offering a challenging 13.1 mile or 10K on steep, technical trails and sweeping views. Limited entries sell out fast so register early.

Enjoy a scenic 5 mile trail race at Muscoot Farm on October 19, 2025, with fun kids races and post race Farm Bucks to spend at the farmer's market. T shirts require advance order and dogs are not allowed on the farm.

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..

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.

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..

Join the 9th annual Fall Back into the Trails at Red Wing Recreation Area in Lagrangeville NY for two days of scenic, supported loop trail racing with 10K 50K and 100K options. Custom finisher medals, camping and UTMB index for longer races..

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..

Event information The People in Need - Day of the Dead 5K is scheduled for Sunday, November 2, 2025, in Fresh Meadows, New York. The event is a charity 5K walk/run organized to raise funds and awareness for People in Need. The event locatio..

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 Veterans Day Cross Country 4K Run, hosted by the Northport Running Club, is held at the Veterans Administration Medical Center Golf Course in Northport, NY. The English-style 4K course runs entirely on grass (about 2.48 miles) with no p..

Choose Marathon or Half Marathon on a single loop through Rockefeller Preserve, a rolling hilly course with Hudson River and Palisades views amid fields, forests and stone walls. Proceeds support local conservation groups.

Event overview The Beacon Bonfire 10K takes place in Beacon, NY on Saturday, November 8, 2025. The event is a 10K trail race that starts and finishes at the Mt Beacon Trailhead. Registration closes Thu, Nov 6 at 11:59 PM ET. The race has a..