Trail Running calendar near Rocky Point 2026-2027

A single-loop trail half marathon through five parks in lower Westchester County, New Rochelle. Most of the course is on dirt and wooded trails and passes through areas with visible wildlife.

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 trail 5K at Blydenburgh County Park on October 11, 2026 with a shaded mixed-surface course, participant tee, on-site refreshments and parking details. A virtual 5K option runs Oct 11 to Oct 18 and includes a shirt and bib name.

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.

HHNC Meadows & Trails 5K is an off road 5K at Hudson Highlands Nature Center in Cornwall NY on 10/17/2026, featuring meadows, ponds, wooded trails and views of Black Rock Mountain. Entry is $35 and children under 18 run free.

The Livingston Oval Marathon will take place in Livingston on Saturday 17 October 2026. You can run between 21 and 42 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* through interconnected woodland preserves in Guilford, Connecticut, featuring rocky single track and rolling forest roads. The course is set for experienced trail runners and has limited entries.

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 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.

A trail-based 5K and family 1 mile fun run in Poricy Park with a Halloween costume theme and prizes, raising funds for 180 Turning Lives Around. Options include a timed 5K, a fitness walk, and a family fun run.

A trail event at Muscoot Farm on October 25, 2026 featuring a 5 mile race plus two kids courses for ages 7 to 12 and 6 and under. Packet pickup and parking are provided and participants receive Farm Bucks and kids medals.

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 half marathon, 5K and a kids fun run in Garrison, NY on October 25, 2026, benefiting the Friends of Philipstown Recreation. The courses run through Hudson Highlands State Park and pass Osborn Castle on private property reserved for re..

A trail running event at Red Wing Recreation Area near Lagrangeville, NY, offering 100k, 50k and 10k looped courses with on-course aid, finisher medals and awards for top male and female finishers.

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 in Penwood State Park featuring technical single track on the Metacomet Trail and rocky runnable terrain. No aid stations so runners must carry hydration for 6.2 miles; proceeds partly support NAMI.

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.