Tarrytown
Trail Running Calendar near Tarrytown 2026-2027
Explore the top trail runs near Tarrytown 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.
November 2026
A scored cross country 5K at Van Cortlandt Park on November 15, 2026, open to ages 8 and up, run on wooded trails with on-site awards and race-day amenities.
A farm based 5K trail run plus a kids fun run for ages 6 and under in Yorktown Heights supporting Friends of Hilltop Hanover Farm.
A community 5K at Inwood Hill Park on November 26, 2026, with proceeds to the Inwood Food Pantry, personalized bibs by 11/1, and medals for the first 700 finishers.
A community 5K run and virtual option at Alley Pond Park on November 26, with a free kiddie dash, on-course refreshments, and proceeds supporting the Never Stop Running Foundation.
Community Thanksgiving event at Somers High School with a 5K and 1-mile fun run, shirts, medals, age-group awards, and scheduled packet pickup days.
Charity 5K and timed 1 mile walk/run at Darien High School on November 27, 2026 supporting The Depot, with family activities and bib pickup options.
Trail party at South Mountain Reservation on November 28, 2026 with 5K, 10K, 25K, 50K and Kids 1M options on mixed carriage roads and technical singletrack.
A revived 9 mile cross-country race in Van Cortlandt Park covering three loops of the park’s XC course with awards, commemorative buffs, and a post-race pub gathering.
A 5K trail race at Stillwell Woods Preserve in Woodbury supporting The Center for Developmental Disabilities and held in memory of a community runner.
Winter trail races in Ringwood NJ with a 13.1 mile half, 10K and 5K on mostly singletrack, significant elevation, and RideWithGPS navigation access.
December 2026
Third annual 5K Reindeer Run/Walk on the Joel Barlow cross-country course in Redding, CT with festive attire encouraged and proceeds to the Class of 2029.
A 5 km park race at Van Cortlandt Park on December 12, 2026, presented by Race The Bronx and Cash Cow NYC with race T shirts and bag check.
A 5 mile winter trail race at Mountain Lakes Park in North Salem NY with start and finish in the Yurt Village, a central firepit, and proceeds supporting park trail projects.
January 2027
A trail party in West Orange, NJ with a 5K loop and timed 3- and 6-hour loop events, raising funds for the South Mountain Conservancy.
February 2027
March 2027
Trail race in South Mountain Reservation, West Orange NJ offering 11M, 20M, 50K and 50M across three marked loops with varied terrain and a 400-person cap.
April 2027
Mountain 10K and half marathon in Bear Mountain NY on rugged technical trails with steep climbs, scrambling, and mandatory safety gear.
A community trail event in Cross River, NY featuring a 5k trail race, a 4k walk on the same trails, and a 200 meter kids dash on the contest track.
A community 5K running event in Woodhaven, NY on April 10, 2027 supporting Jamaica College and its Penn Relays Team; registration fee $20.
A scenic all-terrain 5K and a 0.3 mile kids fun run at Stamford Museum and Nature Center on April 11, 2027, with farm views and a free kids educational dropoff.