Pawling
Trail Running Calendar near Pawling 2026-2027
Explore the top trail runs near Pawling for 2026-2027! We've gathered 28 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
September 2026
Timed trail event in Pawling, NY with 3, 6, 12, and 24 hour races on an about 1.68 mile loop, aid station, crew area, and finisher medals.
Trail races in Ridgefield CT offering a single loop of about 4.25 miles or a double loop of about 8 miles through Hemlock Hills and Pine Mountain. The technical, rocky course starts and ends at the Lake Windwing ballfields.
October 2026
A veteran-run series of elevation-based mountain endurance events at Mohawk Mountain CT and Amicalola Falls GA, offering seven solo and team formats from 12 to 84 hours.
A trail half marathon in Cold Spring NY covering 13.7 miles with 4,000 ft of climb through the Hudson Highlands while supporting the NYNJTC.
A timed 5K and accessible short run and walk at private Gemstone Farm in Wilton, CT with race shirt, post-race food, music, and support for The Prospector's mission.
Trail races at Mohawk Mountain Ski Area on October 11, 2026 offering 5K, 10K, Half Marathon and Marathon over steep ski slopes and forest trails.
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.
Trail event at Muscoot Farm in Katonah on October 25, 2026 featuring a 5 mile race and two kids races, with Farm Bucks and kids medals.
Trail half marathon, 5K and a 3/4 mile kids run in Garrison NY, fundraising for The Friends of Philipstown Recreation with a course that passes Osborn Castle.
A multi-day trail running event at Red Wing Recreation Area near Lagrangeville, NY offering 100k, 50k and 10k looped courses with aid, medals and UTMB Index status.
November 2026
Timed trail running on a 4 mile loop at Gurski Farm in Brookfield CT with 8 hour and 4 hour options plus a new 5K Canicross for 2026.
Trail events at Ward Pound Ridge Reservation: a 10k trail race on November 8, 2026 and a month long Raven 100k Challenge with wooden finisher medallions.
Trail race at Tarrywile Park offering Marathon, Half Marathon and 10K on a loop course with roughly 3K of elevation and technical single-track.
A community 5K and a 1-mile kids run at Sargent Elementary in Beacon, NY, with a food drive, live DJ, and refreshments.
A ninth annual charity 5K in Roxbury, Connecticut on November 26, 2026, with a 3.1 mile out-and-back course near Everett B. Hurlburt Community Park. Proceeds support local ambulance and scholarship funds and a food pantry collection.
Somers Thanksgiving Turkey Trot in Somers, NY features a 5K trail race and a 1 Mile fun run with age-group awards, shirts, medals, and packet pickup.
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.