Pleasantville
Trail Running Calendar near Pleasantville 2026-2027
Explore the top trail runs near Pleasantville for 2026-2027! We've gathered 39 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
October 2026
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.
Half marathon and 5K in Garrison NY through Hudson Highlands and past Osborn Castle with proceeds supporting Friends of Philipstown Recreation.
November 2026
A trail event at Ward Pound Ridge Reservation featuring a 10 km race, a November 100 km virtual challenge, rugged climbs, and fundraising for the Friends of Trailside Museum.
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 scored 5K cross country race at Van Cortlandt Park on November 15, 2026, featuring youth programming, volunteer opportunities, live app tracking, and post-race awards.
Inwood Hill Turkey Trot is a community 5K run/walk through Inwood Hill Park in New York City, offering live result updates, free finish line photos, awards for the top two men and women, and proceeds that support the Inwood Food Pantry.
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.
February 2027
April 2027
A community trail event in Cross River, NY featuring a hilly wooded 5K, a 4K walk through the main trail, and a 200 m kids dash on the contest track. Registration opens 8/24/2026 with limited pre-registration t-shirt incentives.
A spring 10K trail race in Cross River NY on April 25 2027, organized by Leatherman's Loop Races. Entry is by lottery with registration Jan 8 to Jan 11 2027 and the $58 fee includes the park entry.
May 2027
VCP 50K is a looped trail ultramarathon in Van Cortlandt Park on 01 May 2027. The 50K course starts with a flats lap then ten cross country loops, with stocked aid stations, drop bag access, finisher medal, singlet, meal and beer.
A 5 mile trail race at Muscoot Farm on May 23, 2027 with two kids races on farm trails. The event is organized by Run the Farm Races and is sanctioned by USA Track and Field.
June 2027
Trail races at Ward Pound Ridge Reservation on June 6, 2027 include a half marathon and a 10k that pass the summit where the historic fire tower is being reconstructed. Proceeds support Friends of the Fire Tower for accessibility and educational impr..
July 2027