Trail Running calendar near Pawling 2026-2027

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.

A Halloween themed event on Clinton Road in West Milford, NJ offering a 1 mile Zombie Crawl plus 5k and 10k races. The course features zombie volunteers, themed aid stations, and a finish line festival with awards and a costume contest.

An off road 50k around Guilford, Connecticut, on rolling forest roads and rocky single track. The not for profit race supports local land conservation, awards finishers within a 10 hour limit, and offers volunteer opportunities.

Trail and 5K races at Hillside Park on October 18, 2026, benefit a free mammography program. A kids fun run for ages 5 to 12 is included, with chili and vegetarian food and timing by Compuscore.

Trail event at Mt Tom State Park on October 24, 2026 offering 25k and 10k courses, a 25k two person relay, and an untimed 5k fun run or hike. Proceeds support Kestrel Land Trust conservation work.

A community trail event at Ives Farm featuring a 5K trail race, a youth team relay, and a free kids Pumpkin Dash, plus family activities and proceeds supporting local YMCA and land trust projects.

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.

A Spartan obstacle weekend at Sunflower Valley Farm in New Hampton, NY featuring Sprint, Super, Kids races and Hurricane Heat formats across woods, mud, fields and creek runs. Team entries and GOVX discounts are available.

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.

Experience a unique timed trail event at Gurski Farm featuring a four mile loop of rolling farm trails and single track. Choose between eight hour, four hour, or 5K options in a community focused environment.

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 community 5K and 1 mile walk on November 8, 2026 at Central Park of Morris County supporting Family Promise of Morris County, with in-person and virtual 5K options and age-group awards.

A charity trail event at Hillside Park on November 8, 2026, offering 10 km and 5 km races to benefit a free digital mammography program, with race timing, age-group medals and participant T-shirts.

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.

Experience the diverse terrain of South Mountain Reservation with a looped trail race offering 5K, 10K, and half marathon distances. Enjoy a mix of single track and fire roads with support provided at regular aid stations.

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 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.