Yorktown Heights
Trail Running Calendar near Yorktown Heights 2026-2027
Explore the top trail runs near Yorktown Heights for 2026-2027! We've gathered 45 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
November 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.
An inaugural backyard ultra at Cranbury Park where runners repeat a 4.167 mile loop each hour until one runner remains, with crew access and central aid near the corral.
Trail race at Tarrywile Park offering Marathon, Half Marathon and 10K on a loop course with roughly 3K of elevation and technical single-track.
Scored 5K cross country at Van Cortlandt Park in the Bronx on November 15, 2026, with youth races, live tracking, and on-site awards.
A community 5K and a 1-mile kids run at Sargent Elementary in Beacon, NY, with a food drive, live DJ, and refreshments.
A 5K run and walk through Inwood Hill Park on November 26, 2026, with proceeds benefiting the Inwood Food Pantry and options for early and race-day bib pickup.
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.
February 2027
April 2027
Mountain trail event at Bear Mountain NY offering 10K, 13.1 mile and ruck divisions on rugged technical singletrack with steep climbs and significant elevation gain.
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 USATF sanctioned 10K trail race in Cross River NY on April 25, 2027, with entry via lottery and a $58 registration fee that includes 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..