Trail Running calendar near Midtown Manhattan 2025-2026

Run The Farm is a scenic 5 miles trail race at Muscoot Farm in Katonah, NY, with kids races and a festive farm market finish. Enjoy trails, local treats, and community spirit in spring and fall editions.

C'mon Armageddon brings technical trail running to Norvin Green Park in West Milford, NJ with 50K, 10 mile and 5 mile routes through boulder fields, river crossings and steep climbs. Expect rugged singletrack and a raw mountain challenge.

Tackle the Mine Hill Half Marathon, a scenic road race that climbs hard in the first half then rewards you with a fast mostly downhill return to Mine Hill Distillery in Roxbury. Finishers get a medal and a lively post race celebration.

Run lakeside singletrack at Dickerson Mine Preserve on scenic mostly flat trails. Choose 21K half marathon, 10K or 5K, then enjoy Black River Barn with outdoor dining and beer on tap.

Join Pinky's Rock n Rolla, a 4 mile trail race through Forest Park's scenic trails in Richmond Hill, NY. Enjoy rugged natural terrain, medals for all finishers, prizes for top runners, and proceeds benefiting Puppy Kitty NYCity.

Run the Ridge Reaper at Ward Pound Ridge Reservation with 25K, 50K, and 50M courses through technical singletrack and scenic carriage roads. Big climbs, ridge views, and a cupless format so carry your own hydration.

Take on the Interstate 17 Trail Run, a 17 mile looped trail race at State Line Lookout with serious elevation and rugged technical terrain. Rocky scrambles, waterfalls and required loop check ins make this a scenic tough challenge.

Tackle technical trails at Stokes State Forest with options from a 5K to a challenging 17 mile loop, plus ruck divisions for 10K. Finishers earn a handcrafted wooden medal and unique swag.

Tackle technical single track and big climbs at the Macedonia Trail Race in Kent, Connecticut. Choose 12K, 25K, or 50K loops with Cobble Mountain views and rugged trails for a rewarding, scenic challenge.

Three days of trail racing and community at Wawayanda State Park, with distances from 100 mile to a kids mile. Friday panels and a trail film, free camping, and a partnership with Bigger Than The Trail supporting mental health.

Tackle a scenic half marathon loop through five parks in Westchester, starting at the Thomas Paine Cottage and finishing at New Rochelle High School. Mostly wooded trails, rocky roots and abundant wildlife make this a classic trail escape.

Test your legs on rugged singletrack at Harriman State Park with Big Bear SquaTCh South, a half marathon or 10K on Oct 18, 2026 that supports trail maintenance. Limited to 175 runners, this sold out favorite features steep climbs rocky root..

Enjoy a scenic 5 mile trail run through historic Muscoot Farm in Katonah, with fun kids races and farm market perks. Finishers get Farm Bucks to spend at the market, making this a perfect fall family run and local food celebration.

Run or walk the family friendly Never Stop Running Foundation Long Island Turkey Trail Trot, a scenic 5K through Bethpage State Park on November 14, 2026. Enjoy post race refreshments and a festive community atmosphere.

Run 13.1 miles on forest trails at the Storybook Half Marathon in Roosevelt Forest, Stratford CT, completing eight scenic loops of single and doubletrack. Wear a costume, enjoy post race perks, and donate children's books to Books4Everyone.