Pleasantville
Trail Running Calendar near Pleasantville 2026-2027
Explore the top trail runs near Pleasantville 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.
August 2026
50K loop ultramarathon in Forest Park Queens with 12 laps of the 2.5 mile Orange Trail, about 300 feet climb per lap and an aid station after each lap.
A 52 day certified road race in Jamaica, Queens where athletes aim to cover 3100 miles on a 0.5488 mile loop, averaging about 59.6 miles per day.
September 2026
Multi-distance trail festival at Ringwood State Park Sept 18–20 2026 with looped courses, a central aid station, and options from a kids mile to 100 miles.
Trail ultrarace in Upper Nyack, NY with a 50 mile and a 27 mile course featuring roughly 9,700 and 4,900 feet of elevation gain.
Trail races in Ridgefield CT offering a single loop of about 4.25 miles or a double loop of about 8 miles through Hemlock Hills and Pine Mountain. The technical, rocky course starts and ends at the Lake Windwing ballfields.
Front Runners New York's annual 5K cross country meet at Van Cortlandt Park on September 26, 2026, includes participant sunglasses and age-group awards.
A scenic 3.1 mile road and trail run through the New York Botanical Garden with a stretch in the Thain Family Forest and post-run festivities on Daffodil Hill.
A scored NYRR cross country race at Van Cortlandt Park featuring a 5K course as the first event in a three-race fall series, with youth programming via Rising NYRR.
October 2026
Four miles of trail running through the Irvington Woods with varied terrain and stairs, starting and finishing at the Irvington High School campus on October 4, 2026.
A trail half marathon in Cold Spring NY covering 13.7 miles with 4,000 ft of climb through the Hudson Highlands while supporting the NYNJTC.
Scored cross country 5K at Van Cortlandt Park in the Bronx, part of an NYRR series that includes youth races, accessibility provisions, and official results via the NYRR app.
A community 5K and 2 Mile Walk at Garrett Mountain on October 11, 2026, with virtual and Tot Trot options; proceeds benefit the Fred Torres Memorial Scholarship Fund supporting Clifton High School athletes.
A timed 5K and accessible short run and walk at private Gemstone Farm in Wilton, CT with race shirt, post-race food, music, and support for The Prospector's mission.
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 trail half marathon in New Rochelle that loops through five Westchester County parks and runs mostly on dirt trails shaded by woodland canopy.
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 half marathon and 10K through Harriman State Park near Tuxedo NY, featuring steep climbs, rock fields, and significant elevation gain.
Community 5K at Garret Mountain in Woodland Park supporting Autism awareness, with vendors, free gifts, $25 registration, and medals for special needs children.
Trail event at Muscoot Farm in Katonah on October 25, 2026 featuring a 5 mile race and two kids races, with Farm Bucks and kids medals.
Trail half marathon, 5K and a 3/4 mile kids run in Garrison NY, fundraising for The Friends of Philipstown Recreation with a course that passes Osborn Castle.