Woodbury
Trail Running Calendar near Woodbury 2026-2027
Explore the top trail runs near Woodbury for 2026-2027! We've gathered 43 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
October 2026
A 4 miles trail race through Irvington Woods with varied terrain and stairs, starting and finishing at the Irvington High School campus.
Four-day trail event in Rocky Point, NY featuring a 10.48-mile Pine Barrens loop with eight distance options from 10 miles to 150 miles.
A timed trail 5K at a private 150-acre farm in Wilton CT with an accessible short run, live music, food, and proceeds supporting The Prospector.
A scenic October 5K on the carriage roads of Rockefeller State Park Preserve with hilly terrain, awards, and proceeds supporting carriage road maintenance.
Trail half marathon in New Rochelle running a single loop through five Westchester parks on mostly dirt shaded trails with frequent wildlife on October 11, 2026.
A scenic trail 5K at Blydenburgh County Park on October 11, 2026 with in-person and virtual options, race tee, refreshments, and age-group recognition.
Multi day running weekend in Bay Shore, NY with marathon, half marathon, 10K, 5K, kids 1K, relay and a virtual 26.2 miles challenge.
A community 5K and kids fun run in Massapequa Park supporting officer mental health and suicide awareness, with medals, awards, and finish-line photos.
November 2026
Community 5K and untimed fun run on November 7, 2026 at Sachem North High School in Lake Ronkonkoma NY, offering shirts, live results, photos, and age group awards.
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.
A 5K run and virtual 5K at Belmont Lake State Park on November 8, 2026 featuring a scenic lakeside course, a free kiddie dash, event swag, and age-group recognition.
Championship cross country at Bethpage State Park on November 8, 2026 featuring an 8K Open, Masters and Para Athletic competition with individual and team awards.
A family-friendly trail 5K at Bethpage State Park on November 14, 2026 with in-person and virtual options, a free Kiddie Dash and post-race refreshments.
Inaugural Great Lawn Backyard Ultra at Cranbury Park asks runners to repeat a 4.167 mile loop each hour until one person remains.
A farm-based memorial 5K and kids fun run on 11/14/2026 at the Suffolk County Farm and Education Center raising funds for pancreatic cancer research.
A 5K run/walk in Inwood Hill Park on November 26, 2026, benefiting the Inwood Food Pantry with live results and free finish-line photos.
Thanksgiving Day 5K run plus a 1/2 mile fun run at John J Burns Park in Massapequa supporting the John Theissen Children’s Foundation and the Leukemia and Lymphoma Society.