Trail Running calendar near Ansonia 2026-2027

A pickle-themed Halloween obstacle event in Wallkill, NY with an adult 5K and a 1K kids course, themed medals, costumes, mud, and a community-focused Donate a Dragon 3D printing project.

A scenic trail 5K at Blydenburgh County Park in Smithtown, NY on October 11, 2026, with in-person and virtual options, a free kiddie dash, event tee, refreshments, and age group recognition.

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 non-profit off road 5K at the Hudson Highlands Nature Center in Cornwall NY on October 17, 2026. The route passes ponds, meadows, grassy paths and wooded trails while supporting nature-based education; children under 18 run free.

Big Bear SquaTch South is a trail running event at Harriman State Park on October 18, 2026 offering a technical half marathon and a 10K with steep climbs, marked courses, aid stations, and capped fields.

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 starting at Guilford Lakes School that runs through linked woodland preserves on rocky forest road and single-track terrain. The course avoids repeated loops and recommends recent marathon-level experience.

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.

A fall trail race at Mt. Tom State Park on October 24, 2026, with single and relay options from 5k to 25k on rugged single-track terrain. The event supports Kestrel Land Trust and includes aid stations, medical crews, and awards.

A community run at Ives Farm hosted by Cheshire Community YMCA and Cheshire Land Trust. Features a trail 5K, a youth Y Cup relay with elementary teams, a free Pumpkin Dash for young children and family fall activities.

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.

Trail races in the Hudson Highlands near Garrison NY featuring a Half Marathon, a 5K that follows river and historic paths, and a kids costume run on the recreation center grounds.

The Tri-State New York Spartan Event Weekend at Sunflower Valley Farm on Oct 31-Nov 1, 2026 offers Sprint, Super, Kids races, Hurricane Heat formats, wooded muddy terrain, creek runs, and Spartan obstacles for competitors and spectators.

A trail race weekend at Red Wing Recreation Area in Lagrangeville, NY offering 100k, 50k and 10k loop formats with on-course aid and finisher awards; the 50k and 100k are UTMB Index races.

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.

A 10K trail race at Penwood State Park in Bloomfield, CT on November 1, 2026. The rolling loop follows mostly technical single track on the Metacomet, Orange and Yellow trails, has no on course aid station and a three hour cutoff.

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.