Trail Running calendar near Pawling 2026-2027

A trail event at YMCA Camp Sloper on November 21, 2026, offering a 400 minute timed loop option and a two mile two lap race, with chip timing, a central aid station, and proceeds supporting local organizations.

A *5 miles* lollipop loop trail race in Lewis Morris Park, Morristown NJ, run mostly on the Yellow Trail with roughly 600 feet of elevation gain. The event limits entries to 120 runners, uses cupless stations and hemp bibs, and offers free..

A community Thanksgiving trail event on 11/26/2026 at Mill Pond Way Trail with a 3.5 mile run or walk, chip timing, post race yoga for participants, free water and snacks, and proceeds benefiting endometriosis research.

A 5K run and walk through Inwood Hill Park in northern Manhattan with a shared start and finish, live results and free finish line photos. Proceeds benefit the Inwood Food Pantry and awards are given to the top two men and women.

A trail party at South Mountain Reservation offering looped 5K terrain and distances from Kids 1M to 50K. The course mixes carriage roads and technical singletrack and features an aid station at the start finish and a charity partner.

Experience a 5K trail race through the scenic Stillwell Woods Preserve in Woodbury. This event honors the memory of Rob Lauterborn and supports the Center for Developmental Disabilities.

Challenge yourself on the historic Tower Trail at Sleeping Giant State Park. Choose between 4 or 8 hours to complete as many 3.3 mile loops as possible on this scenic gravel path to the Observation Tower.

Trail races at South Mountain Reservation feature 5K, 10K and 13.1 miles on looped courses over fire roads, single track, hills and pavement, with aid about every three miles and race day registration available.

A looped ultramarathon in Prospect Park, Brooklyn offering 50 mile and 50 kilometer options. The course uses 3.33 mile loops and includes on course hydration and a potluck style aid station.

A forest trail 5K in Roosevelt Forest, Stratford, CT on December 19, 2026, where participants may run, jog, hike, or walk in costume. Awards go to the three fastest men and women and all finishers receive a commemorative item.

Trail races at South Mountain Reservation include 5K, 10K and 13.1 mile looped courses with aid stations every 3 miles. Courses use fire roads, single track, hills and some pavement and offer advance and day-of registration.

A winter trail party on a 5K loop offering 5K, 3 hour, 6 hour, and 3 hour rucking divisions, with proceeds benefiting the South Mountain Conservancy. The course mixes carriage roads and technical singletrack with about 300 feet gain per loo..

A onesie-themed 5K at Ramapo Valley County Reservation on February 14, 2027, run on a flat scenic loop around Scarlet Oak Pond. The event is capped at 200 participants, has no cutoff, offers adaptive support, and includes a finisher medal.

Trail races on a 10 mile loop at South Mountain Reservation offering 50M, 50K, 20M and 10M with marked trails, three aid stations per loop, timing, SWAG, and awards for top three male and female finishers.

A timed loop event at Livingston Oval where runners cover as many laps as possible in one, three, six or twelve hours on a USATF certified flat course, with aid stations and awards for top male and female finishers.

A multi-loop trail race at South Mountain Reservation offering 11M, 20M, 50K and 50M options on three marked loops with varied terrain, significant elevation gain, a single finish-area aid station, and support for the South Mountain Conserv..

A 5K trail run and walk at Bethpage State Park with a free kiddie run and virtual option. On-course hydration, post-race refreshments, age-group recognition, and proceeds support the Never Stop Running Foundation.

A spring trail out-and-back on the Nipmuck Trail near Bigelow Hollow, advertised as 16 miles on technical, blazed singletrack with minimal aid and limited parking; proceeds support local trail stewardship.

A community 5K run and free kiddie run on the soft trails of Bethpage State Park, supporting the Never Stop Running Foundation. The event includes in-person and virtual options, refreshments, bib mailing, and age-group recognition.

A mountain trail event at Harriman State Park on April 3, 2027 offering a half marathon, a 10K and a 10K ruck on rugged technical trails with significant elevation gain. Entry is capped at 400 and proceeds support trail maintenance.