Pleasantville
Trail Running Calendar near Pleasantville 2026-2027
Explore the top trail runs near Pleasantville for 2026-2027! We've gathered 44 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
August 2027
A 5K held inside Yankee Stadium on August 8, 2027 with in-person and virtual options, chip timing, and a race medal and shirt for participants.
A multi-day August 2027 event at Sacred Heart University with 90 minute stair climb and walk challenges plus a five day virtual step challenge supporting Homes for the Brave.
A 17 mile trail race at State Line Lookout in Closter NJ featuring four mile technical loops, rock scrambles, stocked aid stations and significant elevation with serious hazards.
September 2027
A multi-day trail festival at Wawayanda State Park near Hewitt NJ with races from a kids 1 mile up to 100 miles, timed 36 hour options, panels, camping and aid stations.
A community 5K run and walk at Forest Park Queens with a free 1K kids run, participant T shirts, awards, live results, and same day photos.
October 2027
Trail half marathon and 10K at Harriman State Park in Tuxedo NY, co-hosted by Sassquad and the New York-New Jersey Trail Conference; proceeds support trail maintenance.