Pleasantville
Trail Running Calendar near Pleasantville 2026-2027
Explore the top trail runs near Pleasantville for 2026-2027! We've gathered 47 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
November 2026
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 5K run/walk in Inwood Hill Park on November 26, 2026, benefiting the Inwood Food Pantry with live results and free finish-line photos.
A Thanksgiving 5K at Alley Pond Park with in-person and virtual options, a free kiddie dash, race shirt and post-race refreshments.
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.
A community Thanksgiving run at Darien High School featuring a 5K and 1-mile walk/run, with music, food, and proceeds benefiting The Depot youth center.
A 5K trail race at Stillwell Woods Preserve in Woodbury supporting The Center for Developmental Disabilities and held in memory of a community runner.
Nine mile cross country race in Van Cortlandt Park using three loops, with commemorative buffs for early registrants and awards from Lloyd's Carrot Cake.
December 2026
A 5K race at Van Cortlandt Park on December 12, 2026, with tiered registration pricing, bib pickup at the Tortoise and Hare Statue, 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.
February 2027
April 2027
Mountain trail races at Bear Mountain on April 3, 2027 offering 13.1 mile, 10K and 10K ruck on rugged technical singletrack with significant elevation gain.
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.
Youth trail run at Katonah Memorial Park for ages 4 to 16 with 0.5 mile and 1 mile options; registration opens January 31, 2027.
A USATF sanctioned 10K trail race in Cross River, NY on April 25, 2027, with entry by lottery and a $58 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