Tarrytown
Trail Running Calendar near Tarrytown 2026-2027
Explore the top trail runs near Tarrytown for 2026-2027! We've gathered 44 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
October 2026
Trail event at Muscoot Farm on Oct 25, 2026 with a 5 mile race, two kids races, Farm Bucks and medals for young finishers.
Autumn races in Garrison NY featuring a half marathon, 5K and a 3/4 mile kids run with a course through Hudson Highlands and past Osborn Castle.
A community 5K run/walk in Forest Park, Queens on October 25, 2026, with a free 1K kids run, participant T-shirts, and medals for early registrants and top finishers.
November 2026
A 4K grass cross country event at the Northport VA Golf Course with military and youth categories, a short fun run, awards, and proceeds supporting local veterans.
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.
An inaugural backyard ultra at Cranbury Park where runners repeat a 4.167 mile loop each hour until only one runner completes a lap.
A community 5K in Clifton with age group awards, special category honors, and post race music, raffles and health booths.
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.
A Thanksgiving 5K at Alley Pond Park with a three-loop course, a free kiddie dash, virtual option, race shirts, and donations supporting the Never Stop Running Foundation.
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.
Looped trail event at South Mountain Reservation on Nov 28 2026 offering distances from a Kids 1M up to a 50K with aid, adaptive support, and a cupless policy.
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.