Trail Running calendar near Roxbury 2026-2027

A community memorial run in Hinckley, NY offering an in-person five-mile trail run/walk, a virtual five-mile option, and a kids fun run; proceeds support a memorial scholarship for students pursuing medical training.

A timed charity tower climb at Empire State Plaza in Albany that reaches the 42nd floor with 809 steps. Water stations, bailout floors and medics are provided; registered participants receive a t shirt and finisher's medal.

Point to point 26 miler in the Slide Mountain Wilderness with nearly 7,000 feet of vertical gain and multiple aid stations; proceeds support land conservation.

A 50K and 25K trail event on the McDade Trail in Milford PA, out and back along the Delaware River with three aid stations and a cupless course.

A community 5K on September 27, 2026 in Dolgeville along the Greenway Trail. Registration has a $25 fee with children under 12 free; proceeds fund free sports equipment for local youth.

A trail running event in Gardiner, NY offering a 5 km run, an optional 10 km two-lap route and a 200 yard kids run, with pre registration T shirt incentives and a sneaker recycling program.

Experience an ultimate endurance test at Mohawk Mountain by taking on 61 miles and 29,155 feet of elevation gain. Participants have 72 hours to run hike or walk their way to an Everest sized vertical achievement.

A 24 hour Backyard Ultra trail event at Mohawk Mountain Ski Area in Cornwall, CT, featuring about 14,400' of elevation and options to run, hike or walk.

Timed endurance event in Cohoes, NY on Oct 3, 2026 with 1 hour, 3 hour and 6 hour solo and relay options supporting Flutters of Hope.

A fall trail race day in Norfolk, CT offering 5K, 10K and a half marathon with steep climbs, private-trail sections, a cupless policy with water stations, and on-site food and beverage vendors.

Trail half-marathon in Cold Spring NY on October 4, 2026 featuring 13.7 miles and 4,000 ft of gain through the Hudson Highlands; proceeds support NYNJTC.

Trailwagger at Gilbert Lake State Park on October 10, 2026 features 3, 5 and combined 8 mile courses, a two person team division, and a dog stroll. A portion of proceeds supports a local animal shelter.

Community 5K and a 0.5 mile youth run at Pitney Meadows Community Farm on October 10, 2026. The mixed surface, spectator friendly course runs on grass and stone dust and raises funds for the farm's programs.

Trail running at Mohawk Mountain Ski Area with 5K, 10K, half and marathon routes on ski slopes and state forest, cupless aid stations and finisher medals.

A pickle-themed Halloween obstacle event in Wallkill, NY with an adult 5K and a 1K kids course, themed medals, costumes, mud, and a community-focused Donate a Dragon 3D printing project.

The Veeder Tree Farm 5K will take place in Earlton on Sunday 11 October 2026. You can run 5 kilometers.

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.

A technical trail event in Harriman State Park offering 13.1M and 10K on rugged singletrack with steep climbs, limited to 175 participants.

Explore the scenic trails of 100 Acre Woods in Malta, New York. This community event on October 18, 2026 features 2k, 3k, and 5k trail runs. All proceeds support local trail maintenance.

Experience the wilderness trails of Deerfield Town Park with a variety of trail races for all ages. Enjoy a professionally timed 5K or a community run while supporting the local food pantry in your favorite running costume.