Yorktown Heights
Trail Running Calendar near Yorktown Heights 2026-2027
Explore the top trail runs near Yorktown Heights 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.
October 2026
Trail races in Lagrangeville NY with 100k, 50k and 10k loop options, on-course aid, finisher medals, and UTMB Index status.
November 2026
Timed trail running at Gurski Farm in Brookfield CT on a rolling four mile loop with 8 hour, 4 hour, and a new 5K canicross option.
Timed laps at New Canaan High School Track where adults run for 14 minutes and 48 seconds and kids run one 400 m lap, with proceeds supporting the Ram Council Foundation.
A technical 10k trail race at Ward Pound Ridge Reservation with a parallel November Raven 100k Challenge offering badge-based achievements and a wooden finisher woodallion.
A scenic second-annual 5K at the New York Botanical Garden on November 8, 2026, combining road and trail sections with post-run festivities and garden views.
Experience technical single track trails and significant elevation gain at Tarrywile Park with marathon, half marathon, and 10k race options in Danbury.
Scored NYRR cross country 5K at Van Cortlandt Park on November 15, 2026, with wooded trails, bag check, on-site awards, and runner tracking.
A community Turkey Trot at Sargent Elementary in Beacon NY with a 5K Run Walk, a one mile kids fun run, a food drive, live DJ and refreshments.
A memorial 5K run and walk on the cross country course in Danbury offering a chance for friends, family and teammates to gather and remember.
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 at Inwood Hill Park on November 26, 2026, with proceeds to the Inwood Food Pantry, personalized bibs by 11/1, and medals for the first 700 finishers.
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.
Charity 5K and timed 1 mile walk/run at Darien High School on November 27, 2026 supporting The Depot, with family activities and bib pickup options.
A revived 9 mile cross-country race in Van Cortlandt Park covering three loops of the park’s XC course with awards, commemorative buffs, and a post-race pub gathering.
A 5K trail race at Stillwell Woods Preserve in Woodbury supporting The Center for Developmental Disabilities and held in memory of a community runner.
December 2026
Third annual 5K Reindeer Run/Walk on the Joel Barlow cross-country course in Redding, CT with festive attire encouraged and proceeds to the Class of 2029.
A 5 km park race at Van Cortlandt Park on December 12, 2026, presented by Race The Bronx and Cash Cow NYC with race T shirts and bag check.
A 5 mile winter trail race at Mountain Lakes Park in North Salem NY with start and finish in the Yurt Village, a central firepit, and proceeds supporting park trail projects.