Pleasantville
Trail Running Calendar near Pleasantville 2026-2027
Explore the top trail runs near Pleasantville 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.
August 2026
Experience a technical seventeen mile trail run along the Hudson River cliffs with over five thousand feet of elevation change. High endurance is required for this rugged course featuring boulder scrambles and scenic river views.
Step Up for the Brave runs Aug 10–15, 2026 with 90 minute stair climb and walk challenges at Sacred Heart University plus a five day 40,000 step virtual challenge supporting veterans experiencing homelessness.
An evening 3.6 mile trail run through Forest Park in Queens that visits 543 acres of wooded trails with rolling hills. After the run a festival area has music, vendors, food trucks and awards with participant tees provided.
Trail races in Fahnestock State Park near Cold Spring NY offering 50K, 25K and 5.5 mile options with on-course aid and a post-race meal.
On August 23, 2026 Raptor Ridge stages a 6.5 mile trail race at Westmoreland Sanctuary in Mount Kisco, New York. The event starts and finishes at the Fox Lane High School campus, dogs are not allowed and non perishable food donations are collected.
A 50K trail race in Forest Park Queens featuring 12 laps of a 2.5 mile loop with about 300 feet of climb per lap and a published 8 hour cutoff.
September 2026
A USATF-sanctioned trail event in Upper Nyack with a 50 mile option featuring four 11.5 mile loops, about 9,700 feet gain, and three aid stations.
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.
A scenic 3.1-mile road and trail run through the New York Botanical Garden, featuring forest and garden views, post-run festivities, and an included All-Garden Pass.
A scored 5K cross country race at Van Cortlandt Park in the Bronx on September 27, 2026, part of the NYRR Cross Country Series with youth and accessibility programs.
October 2026
A 4-mile trail race through Irvington Woods on October 4, 2026, starting and finishing at the Irvington High School campus; rain or shine.
Trail half-marathon in Cold Spring NY on October 4, 2026 featuring 13.7 miles and 4,000 ft of gain through the Hudson Highlands; proceeds support NYNJTC.
A scored 5K cross country race at Van Cortlandt Park in the Bronx on October 4, 2026 with live app tracking and on site awards.
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 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 single-loop trail half marathon through five parks in lower Westchester County, New Rochelle. Most of the course is on dirt and wooded trails and passes through areas with visible wildlife.
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 event in Harriman State Park offering 13.1M and 10K on rugged singletrack with steep climbs, limited to 175 participants.