Trail Running calendar near Tarrytown 2026-2027

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.

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 noncompetitive winter running series of six loops totaling 66 miles along the Delaware River in NJ and PA. Limited to 100 entrants, the $15 fee includes aid station support and a handmade finisher award.

The HHNC Meadows & Trails 5K will take place in Cornwall on Saturday 17 October 2026. You can run 5 kilometers.

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.

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.

The 4th annual Chesterfield FALL Terrain 5K at Fenton Lane Park on October 18, 2026 features a 5K run/walk and a 1 mile Fun Dash, supports local charities, offers custom race shirts and age group awards.

A trail ultramarathon at Washington Crossing Park on October 24, 2026, offering 25K+ and 50K courses across historic, technical singletrack with multiple aid stations and finisher swag.

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.

The Castle to River Run - Garrison, NY will take place in West Point on Sunday 25 October 2026. You can run between 5 and 21 kilometers.

The inaugural Barnyard Squatch 5K is a hilly trail race across The Barnyard Sanctuary's nearly 200-acre property in Blairstown, NJ, with over 500 feet of climbing and a route past rescued farm animals. All donations go to the sanctuary.

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.

A costumed 5K trail run and walk at Van Scott Nature Reserve on October 31, 2026 with in-person and virtual options to raise awareness for Pregnancy and Infant Loss Awareness Month. Includes a costume contest, water stations, and family act..

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.