Yorktown Heights
Trail Running Calendar near Yorktown Heights 2026-2027
Explore the top trail runs near Yorktown Heights 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.
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.
Test your endurance at the Pawling 24 Hour Trail Running Festival featuring multiple timed races on a scenic 1.68 mile loop in Lakeside Park.
Experience a challenging 50 mile or marathon trail race featuring 9600 feet of elevation gain and scenic Hudson River views at Hook Mountain.
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 fall cross country 5K in Van Cortlandt Park with race day packet pickup, age group awards, live results and a pair of translucent rainbow sunglasses for each participant.
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
A 4 miles trail race through Irvington Woods with varied terrain and stairs, starting and finishing at the Irvington High School campus.
Experience 13.7 miles of Hudson Highlands trails with 4000 feet of elevation gain during the peak foliage season in Cold Spring New York
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 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.
Scenic 5K at Rockefeller State Park Preserve featuring hilly carriage roads, age group and team awards, t shirts and refreshments, with 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.
Trail running at Muscoot Farm with a 5 mile race and two kids races on October 25, 2026 in Katonah, NY.
Trail and road 1/2 marathon, 5K, and kids 3/4 mile run in Garrison NY on October 25, 2026 supporting the Friends of Philipstown Recreation.
Test your endurance at Red Wing Recreation Area with a series of looped trail races ranging from 10k to 100k featuring significant elevation gain and constant support.
November 2026
Experience a community-focused trail race featuring a 4 mile loop of rolling farm trails and single track with timed options, a 4 mile distance, and a 5K Canicross.