Trail Running calendar near Milford 2026-2027

Experience the wooded trails of the historic Ward Pound Ridge Reservation in New York. This event offers 25K, 50K, and 50 mile distances featuring a mix of technical singletrack and runnable carriage roads.

A unique "last person standing" trail run in Kempton, where runners complete 1.6-mile laps against a shrinking clock. The event culminates in a communal post-race gathering with food and sponsored refreshments.

Experience a loop based trail race at the Newbsanity Adventure Center featuring creek crossings and swamps. Choose between 5K, 15K, or 50K distances with an optional rucking class for those seeking a weighted challenge.

A loop-based ultra at Tamaques Park offering 3, 6, 9, 12 and 24 hour events on 0.8-mile loops, with support crews allowed, an on-site aid station, and a fundraising option that can secure a full refund for $500 raised.

Honoring September 11 heroes, this arena climb at TD Bank Ballpark features a 2,200 foot track through stadium aisles. Join a timed stair challenge or a flat concourse walk to support the Tunnel to Towers Foundation.

Experience a technical seventeen mile trail run along the Hudson River cliffs with over five thousand feet of elevation change. High endurance is required for this rugged course featuring boulder scrambles and scenic river views.

A trail running event at Stokes State Forest offering 17 mile, 10K, 10K Ruck and 5K options on technical singletrack. Military participants receive 50% off with code THUNDERCHICKEN.

The third annual Tappen Brook 5K in Bridgewater, CT, uses newly opened trails through Bridgewater Town Park with packed dirt and natural paths and views of Lake Lillinonah. Participants receive a race-day gift and top finishers earn prizes.

Trail races at Fahnestock State Park near Cold Spring NY offer three distances on mixed runnable dirt roads and technical single track. Multiple aid stations and a post race meal are provided and proceeds support park conservation.

A mountain trail event at Belleayre Resort on August 16, 2026 with a demanding 25K and an 8K on ski slopes. The event runs as zero carbon and raises funds for The Catskill Center.

On August 23, 2026 Raptor Ridge stages a 6.5 mile trail race at Westmoreland Sanctuary in Mount Kisco, New York. The event starts and finishes at the Fox Lane High School campus, dogs are not allowed and non perishable food donations are co..

Experience the rugged beauty of Salt Springs Park with technical trail races through old growth forests and wetlands. Choose between 5K, 10K, or a demanding 50K ultra featuring 7,000 feet of elevation gain.

Barn B Q Trail Festival on Saturday 9/5/2026 at Masker's Barn pairs a trail run or hike with a five hour barn party featuring BBQ, drinks, music and games. Ticket options cover adults, designated drivers, and children.

Two mile loop trail event at Horseshoe Bend Park near Frenchtown, NJ, offering distance and timed options from 10K to 100 miles. Central Base Camp appears every two miles with food, supplies, camping, and nearby parking.

A trail event in Rosendale, NY on the Shawangunk Ridge Trail offering 70 mile, 30 mile, and half marathon divisions. The course crosses varied terrain and is minimally supported so participants must carry food and water purification.

A trail event at Hickory Run State Park offering 100K, 50K and 18-mile options on a figure-8 50K loop with a boulder field and a rugged Shades of Death Trail section, set with timed cutoffs and staffed aid stations.

The City Challenge Race returns for its 12th year on the Jersey City waterfront. This is the only event of 2026, featuring a fast 3-mile urban obstacle course with over 20 unique challenges. Participants receive finisher medals, professiona..

Experience a diverse trail race at South Mountain Reservation featuring fire roads and single track trails. Choose from multiple distances ranging from a 5K to 50 miles with aid stations every three miles.

Run along the Lehigh River on the hard packed D and L Trail. This USATF certified course features a consistent downhill grade and serves as a Boston Marathon qualifier in the Poconos.

Test your endurance at Camp Hart with 4, 6, and 12 hour trail races through technical terrain and scenic hills. Enjoy a supported loop course along the Unami Creek with hot food and diverse trail sections.