Woodbury
Trail Running Calendar near Woodbury 2026-2027
Explore the top trail runs near Woodbury for 2026-2027! We've gathered 40 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
October 2026
A scenic October 5K on the carriage roads of Rockefeller State Park Preserve with hilly terrain, awards, and proceeds supporting carriage road maintenance.
Pickle-themed Halloween obstacle event in Wallkill, NY with a 5K adult course and 1K kids course, themed medals, costumes encouraged, and a zip line finish.
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 races at Jungle Habitat in West Milford NJ featuring a 13.2 mile half, a 6.6 mile 10K plus loop, and a 3.4 mile 5K plus with cupless aid stations.
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.
Obstacle course weekend in New Hampton NY featuring Sprint 5 km, Super 10 km, kids races, workshops, and Hurricane Heat endurance events.
Trail ultramarathon weekend in Lagrangeville with 100k, 50k and 10k looped courses, UTMB Index status and continuous on-course aid.
November 2026
A trail 10k at Ward Pound Ridge Reservation on November 8, 2026 plus a monthlong November Raven 100k Challenge with a wooden finisher medallion.
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.
Somers Thanksgiving Turkey Trot in Somers, NY features a 5K trail race and a 1 Mile fun run with age-group awards, shirts, medals, and packet pickup.
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.