Yorktown Heights
Trail Running Calendar near Yorktown Heights 2026-2027
Explore the top trail runs near Yorktown Heights for 2026-2027! We've gathered 41 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
October 2026
A timed trail 5K at a private 150-acre farm in Wilton CT with an accessible short run, live music, food, and proceeds 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.
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.
Trail ultramarathon weekend in Lagrangeville with 100k, 50k and 10k looped courses, UTMB Index status and continuous on-course aid.
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.
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 backyard ultra at Cranbury Park in Norwalk on November 14 with repeated 4.167 mile loops, alternating loop direction every four hours.
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.
A farm based 5K trail run plus a kids fun run for ages 6 and under in Yorktown Heights supporting Friends of Hilltop Hanover Farm.
A community 5K through Inwood Hill Park on November 26, 2026 with proceeds benefiting the Inwood Food Pantry and on-site bib pickup options.
Community Thanksgiving event at Somers High School with a 5K and 1-mile fun run, shirts, medals, age-group awards, and scheduled packet pickup days.
Post-Thanksgiving community races at Darien High School featuring a 5K and a 1 Mile walk/run with proceeds benefiting The Depot youth center.