Tarrytown
Trail Running Calendar near Tarrytown 2026-2027
Explore the top trail runs near Tarrytown 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.
October 2026
A scenic 5K through the carriage roads of Rockefeller State Park Preserve with hilly terrain, Swan Lake views, awards, t shirts and proceeds supporting carriage road maintenance.
A single-loop trail half marathon through five parks in lower Westchester County, New Rochelle. Most of the course is on dirt and wooded trails and passes through areas with visible wildlife.
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.
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.
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.
A multi-distance trail party in West Orange, NJ using a 5K loop with mixed carriage roads and technical singletrack, aid station options, accessibility support, and charity fundraising.
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.
December 2026
An ultramarathon in Prospect Park, Brooklyn on December 6, 2026 offering 50K and 50 mile looped courses with potluck-style aid, Skratch Labs hydration, chip timing, and finisher belt buckles.
January 2027
A January trail party in West Orange with a 5K loop plus timed 3 and 6 hour options, rucking divisions, and fundraising for the South Mountain Conservancy.
February 2027
March 2027
Looped trail race in South Mountain Reservation offering 11M, 20M, 50K and 50M over three marked loops with varied terrain and on-site aid.
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.