Trail Running calendar near Baiting Hollow 2026-2027

A trail 5K and shorter accessible run/walk on 10/10/2026 in Wilton, CT, with event T-shirts, food, beverage, and access to farm grounds. The event supports the Prospectors' mission to create employment opportunities for people with disabili..

Trail races at Mohawk Mountain in Cornwall CT offer 5K, 10K, Half Marathon and Marathon routes with measured elevation gains, ski area trail loops, cupless hydration policy, and aid stations for longer distances.

Experience a premier 13.1 mile trail race through the woods of New Rochelle. This half marathon takes runners across local trails for a focused off road experience in New York.

Experience Long Islands scenic Robert Moses Causeway in this multi day running event. Support local veterans while choosing between marathon, half marathon, 10k, and 5k distances with finisher medals for all participants.

Experience a point to point trail race in Northeast Connecticut on the Airline Trail. Choose between marathon, half marathon, and 10K distances with individual or relay team options to support local student education.

A 3.5 mile trail run and walk on the scenic, flat Mill Pond Trail at Woodtick Recreation in Wolcott CT on October 17, 2026. Tiered online registration is available and a post-event meal is included with registration.

A technical trail half marathon and steep 10K in Harriman State Park with significant elevation gain. Registration supports the New York and New Jersey Trail Conference and hardship and discount options are available.

Experience a unique 50k trail race through interconnected woodland preserves in southern Connecticut. This single loop course features rocky forest roads and single track trails designed to test your endurance and mental stamina.

A fall trail event at Grills Preserve in Westerly with 10 mile and 10 km courses across single-track trails and riverfront sections. Club timing is used, orange clothing is required, and post-race refreshments are provided.

Experience a unique trail race through the forests and meadows of Muscoot Farm. Enjoy distances for all ages followed by a visit to the local farmers market with your farm buck vouchers.

A 5K Run / Walk and Kids Fun Run at Hallock State Park on October 25, 2026, with a virtual 5K option. Proceeds support the Long Island Greenway and include a post-race wine crawl with vendor specials for participants 21 and over.

Experience the Fall Back Into The Trails Series at Red Wing Recreation Area in Lagrangeville. Choose from 100k, 50k, or 10k distances featuring a loop course with elevation gain. This UTMB Index event offers medals and awards.

A timed trail event at Gurski Farm on a 4 mile loop of single track and farm trails. Options include an 8 hour race, a 4 hour race and a 5K plus 5K canicross; the event is cupless with aid at start finish.

Experience a single loop marathon or half marathon on historic carriage roads in the Rockefeller State Preserve. Enjoy views of the Hudson River and stone bridges on a course with no pavement or cars.

A trail running event at Ward Pound Ridge Reservation with a ten kilometer race and a November 100 kilometer virtual challenge. The course features rocky climbs, ridgeline views, and a custom finisher woodallion for challenge completers.

A Thanksgiving themed chip timed 5k at Stonington Vineyards on November 8, 2026. The event features vineyard scenery and includes a t shirt, a portable wine glass, a finisher medal that doubles as a wine stopper and a wine pour.

A multi-loop trail event on Staten Island offering a half marathon, 50K, and 50-mile courses that pass through Blood Root Valley, High Rock Park, and La Tourette Park, with proceeds supporting the Greenbelt Conservancy.

Trail races at Tarrywile Park in Danbury, CT offering 10K, half and marathon on technical single track with significant elevation. Finisher medals, awards and a cash bonus for fast half marathoners.

A November trail race at Burlingame State Park offering 4 mile and 8 mile courses on dirt trails and roads, a required orange garment mandate, post-race food, and age group awards for both distances.

A trail half marathon in Roosevelt Forest featuring eight laps of a 1.64 mile wooded loop with roots, rocks, and rolling terrain. The event includes a book drive, costume prizes, event swag, and podium awards for top finishers.