Trail Running calendar near Ridgefield 2025-2026

Family & Community Services of Somerset County's Taking Strides Towards Wellness 5K Run/Walk is the 13th annual event at Duke Island Park in Bridgewater, NJ. The flat, paved, wooded course runs along the Raritan River, suitable for runners..

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.

The Hot Chili Challenge 8 Mile Trail Run, 5K & Kids Fun Run takes place in Andover, New Jersey. The event features an 8 mile trail run and a 5K for adults, plus a Kids Fun Run for ages 5-12. The atmosphere blends competition with a chili-th..

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.

Join the Veeder Tree Farm 5K on October 19, 2025 for a scenic 5K or 5K Trail Run supporting the Leukemia and Lymphoma Society. Enjoy farm trails, friendly competition, and options for students and virtual participants.

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.

Join the 13th annual Debbie Ann 5K on Sunday, October 19, 2025 for a scenic 5K on the Kittatinny Regional High School cross country course in Newton NJ. Stick around for a family picnic and post race awards.

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..

The Tough Cookie Trail Run 5K is a trail-running event held at Prospect Point Park in Lake Hopatcong, New Jersey. The course is a 5K on local trails, inviting runners, walkers, and hikers to join a morning of strength, spirit, and community..

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..

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..

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..