Woodbury
Trail Running Calendar near Woodbury 2026-2027
Explore the top trail runs near Woodbury for 2026-2027! We've gathered 35 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.
Obstacle course weekend at Sunflower Valley Farm in New Hampton NY with Sprint, Super and Kids races plus an obstacle workshop and Hurricane Heat formats.
Trail races at Red Wing Recreation Area Oct 31 to Nov 1 2026 offering 100k, 50k and 10k looped courses with aid stations and finisher medals.
November 2026
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 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.
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.
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
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.
January 2027
Snowshoe event at Mountain Creek on January 30, 2027 offering a 5 km ridge course and a not timed 1 mile fun option.
February 2027
April 2027
Mountain trail races at Bear Mountain on April 3, 2027 offering 13.1 mile, 10K and 10K ruck on rugged technical singletrack with significant elevation gain.
A community trail event in Cross River, NY featuring a 5k trail race, a 4k walk on the same trails, and a 200 meter kids dash on the contest track.
Youth trail run at Katonah Memorial Park for ages 4 to 16 with 0.5 mile and 1 mile options; registration opens January 31, 2027.
Obstacle course races at Mountain Creek Resort in Vernon NJ on April 24 and 25, 2027, featuring Sprint, Super, Beast, Ultra and kids races.
Two mountain trail races in Ellenville NY on April 24 2027, offering a technical 25K and a 10 mile route with a 6 hour cutoff and limited entry.
25K and 10 mile technical trail races on the Shawangunk Ridge near Ellenville NY, marked courses with cliff views, 6 hour cutoffs, capped at 150 participants.