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.
October 2026
A 4 miles trail race through Irvington Woods with varied terrain and stairs, starting and finishing at the Irvington High School campus.
Trail half-marathon in Cold Spring, NY on October 4, 2026 covering 13.7 miles with 4,000 ft of climbing through the Hudson Highlands; proceeds help NYNJTC.
Community 5K and related races at Garrett Mountain in Woodland Park, NJ, raising funds for the Fred Torres Memorial Scholarship Fund.
A 5K trail run and an accessible short run/walk on private Gemstone Farm in Wilton, CT on 10/10/2026, with farm access, post-event food and entertainment, supporting The Prospector.
A scenic October 5K on the carriage roads of Rockefeller State Park Preserve with hilly terrain, awards, and proceeds supporting carriage road maintenance.
Trail half marathon in New Rochelle running a single loop through five Westchester parks on mostly dirt shaded trails with frequent wildlife on October 11, 2026.
Looped running at Saddle River County Park on Oct 11 2026 with options from 2 miles to 60K, aid stations, official timing, and awards.
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.
Technical trail races in Harriman State Park featuring a rugged half marathon and a steep 10K with substantial elevation gain and marked singletrack.
BLUE 5K RUN in Woodland Park supports children with Autism and families; the mostly trail 5K at Garret mountain features vendors and medals for special needs children.
Trail running at Muscoot Farm with a 5 mile race and two kids races on October 25, 2026 in Katonah, NY.
Trail half marathon and 5K in the Hudson Highlands with a kids costume run and aid stations for the half.
November 2026
A 4K grass cross country event at the Northport VA Golf Course with military and youth categories, a short fun run, awards, and proceeds supporting local veterans.
A trail 10k at Ward Pound Ridge Reservation on November 8, 2026 plus a monthlong November Raven 100k Challenge with a wooden finisher medallion.
Inaugural Great Lawn Backyard Ultra at Cranbury Park asks runners to repeat a 4.167 mile loop each hour until one person remains.
Experience technical single track trails and significant elevation gain at Tarrywile Park with marathon, half marathon, and 10k race options in Danbury.
A community 5K and a 1-mile kids run at Sargent Elementary in Beacon, NY, with a food drive, live DJ, and refreshments.