Trail Running calendar near West Rock 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 **5K** trail run and walk at Blydenburgh County Park on October 11, 2026 with in-person and virtual options. Participants receive a race tee, on course hydration and age group recognition while proceeds benefit a local running foun..

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.

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.

A technical trail event in Harriman State Park offering 13.1M and 10K on rugged singletrack with steep climbs, limited to 175 participants.

An off‑road 50K around Guilford, CT on rocky single track and rolling forest roads, with aid station cutoffs and recommended 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.

A community 5K in Massapequa Park on October 24, 2026 featuring a scenic course through Massapequa Preserve, awards, post-race food and live results.

A trail event at Muscoot Farm on October 25, 2026: a five-mile race plus two kids races, kids medals, and Farm Bucks for finishers.

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.

Half marathon and 5K in Garrison NY through Hudson Highlands and past Osborn Castle with proceeds supporting Friends of Philipstown Recreation.

Obstacle course weekend at Sunflower Valley Farm near New Hampton NY with Sprint 5 km, Super 10 km, kids races, Hurricane Heat formats and spectator options.

Looped trail races at Red Wing Recreation Area in Lagrangeville, NY offering 100k, 50k, and 10k courses with aid stations and finisher medals.

Timed trail event at Gurski Farm in Brookfield CT featuring an 8 hour race, a 4 hour option, and a 5K canicross on a 4 mile loop.

Trail 10K in Bloomfield CT on Nov 1, 2026 honoring Kevin Hutt, run on rocky single track in Penwood State Park with proceeds partly to 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.