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Trail Running Calendar near Woodbury 2026-2027

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Explore the top trail runs near Woodbury for 2026-2027! We've gathered 42 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.

February 2027
A winter trail event at Ramapo Valley County Reservation with a onesie-themed 5K and an optional single-loop fun run on flat gravel trails around Scarlet Oak Pond.
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.
Weekend obstacle course event at Mountain Creek Resort in Vernon, NJ with Sprint, Super, Beast, Ultra and kids races on rugged terrain.
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.
Two day off-road event at Stokes State Forest with trail runs, mountain bike races, triathlon formats, and a paddle triathlon.
A USATF sanctioned 10K trail race in Cross River, NY on April 25, 2027, with entry by lottery and a $58 fee that includes park entry.
May 2027
Trail running on the Shawangunk Ridge with a 50 mile ultra, a marathon, or relay teams, raising funds for Mohonk Preserve on May 1, 2027.
Technical mountain trail races at Breakneck Point, Beacon NY with half and full options, large elevation gain, and on-course aid stations.
A technical mountain trail race in northern New Jersey offering a 50K with over 7000 ft gain plus 10 mile and 5 mile options, map requirements for the 50K, mandatory gear checks, and aid stations on the longer courses.
A community 5K in Ellenville starting and finishing at Aroma Thyme Bistro, with a course along the base of the Shawangunk Mountains and a stretch on the newly resurfaced Rail Trail. Proceeds benefit local food pantries and youth scholarships.
A chip timed 5K at Brooklyn Cider House on May 22, 2027 combining a run or walk with local cider, a shirt, medal, donut and a pour of cider.
A 5 mile trail race at Muscoot Farm on May 23, 2027 with two kids races on farm trails. The event is organized by Run the Farm Races and is sanctioned by USA Track and Field.
June 2027
A lakeside, fully accessible 5K and a rugged 10K up Hook Mountain with 1,300 ft of climb, marked trails, limited field of 200, and adaptive support.
Trail races at Ward Pound Ridge Reservation on June 6, 2027 include a half marathon and a 10k that pass the summit where the historic fire tower is being reconstructed. Proceeds support Friends of the Fire Tower for accessibility and educational impr..
July 2027
A roughly 5 miles trail run through varied terrain at Bowdoin Park in Wappingers Falls, with a 150 runner cap and awards for overall top finishers.
August 2027
A 17 mile trail race at State Line Lookout in Closter NJ featuring four mile technical loops, rock scrambles, stocked aid stations and significant elevation with serious hazards.
September 2027
A multi-day trail festival at Wawayanda State Park near Hewitt NJ with races from a kids 1 mile up to 100 miles, timed 36 hour options, panels, camping and aid stations.
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