Trail Running calendar near Roxbury 2026-2027

An obstacle course event in Binghamton, NY featuring a 3.5 mile course across 100 acres of woods, timed elite and multi lap heats with cash prizes, and untimed open waves where participants receive a shirt and medal.

Towpath Trail Run in Saint Johnsville, NY offers a 10K and 5K on a fully paved, flat course. Timing is provided by TNT Timing and results are posted on the Kuyahoora Kickers website.

A second annual 6k 3.8 mile cross country run at Bruynswick Winery in Gardiner, NY supporting the Ulster County SPCA. The day features music, a meet and greet with shelter animals, awards, and free children's dashes.

A 5K trail run through the orchard at Indian Ladder Farms on May 10, 2026, with a hard cider mimosa provided after the finish and non alcoholic options; top 1st to 3rd place finishers aged 21 and over receive craft cider bottles.

A May race day on the Ashuwillticook Rail Trail offering a marathon, half, 8K and kids mile, with race shirts, finisher medals, aid stations, and proceeds supporting trail maintenance.

Trail running in Pittsfield State Park with 50K, 25K and a 5 mile course on single track and flowy forest trails. The event is organized by BURCS and benefits local animal rescue organizations.

Timed one hour and two hour laps plus a kids run on a 0.8 loop through Ross Park Zoo, with a custom shirt, medal, and zoo admission included; proceeds support the zoo and fundraising can win a Red Panda encounter.

A community 5K in Ellenville on May 17, 2026 that starts and finishes at Aroma Thyme Bistro, follows the base of the Shawangunk Mountains and the newly resurfaced Rail Trail, and finishes with a garden gathering; proceeds benefit local food..

Experience a 5K cross country run or walk through the mowed trails of Peach Hill Park. Reach the highest point in Poughkeepsie for panoramic views and enjoy post race snacks and awards.

Rise of the Obstacles in Wallkill, NY on May 30-31, 2026 features adult and kids obstacle races from a 100 meter sprint to a 2 km multi-lap course, plus a Teddy Bear Crawl nonprofit and a 3D printing fundraiser for youth programs.

A backyard ultra on May 30, 2026 at Trenton Fish and Game Club where runners repeat a 3 1/3 mile loop each hour until one remains or a 30 hour limit is reached. Milestone patches and live online tracking are provided.

Multi-day elevation based endurance events at Mohawk Mountain in Connecticut, June 4 to 7, 2026. Solo, Trail Buddy and Trail Family formats cover timed events from a 12-hour 15-mile option up to 84-hour 152+ miles with large elevation gain.

A trail festival on a 3.8 mile loop featuring a rugged staircase that climbs over 800 feet in less than a mile. Runners can compete solo, join a relay team with flexible lap orders, or take part in a relaxed 1 to 3 lap Fun Run.

Obstacle course races at Bethel Woods Center for the Arts combine rolling trails, forests, and multiple obstacles across Sprint, Super, and kids formats, with workshops, camping, volunteer options, and spectator access during the weekend.

An annual community 5k and kids run that raises suicide awareness and supports families; offers in-person and virtual 3.1 mile options and a 1 mile kids run.

A mountain trail event in Roxbury, NY on June 7, 2026 offering a 6.5 mile race with 3500 ft gain and a 5k with a steep opening climb and downhill finish, with awards and finisher swag.

A flat, non technical trail 5K at Schodack Island State Park on June 7, 2026, with kids races, post race music and a BBQ. Entry fees rise by registration period and kids races cost five dollars each.

A trail festival at Norbrook Farm Brewery with running races, a run and bike duathlon, and mountain bike events on farm road and single track trails. Participants 21 and over receive one free beer ticket and there are finisher medals and aw..

A trail 5K and 10K at Pleasant Valley Wildlife Sanctuary on June 13 featuring mixed single-track and carriage-road terrain, water stations, finish-line food and music, and proceeds supporting local conservation.

A 53 mile, 15,000 foot ultramarathon in the Catskills from Windham to Phoenicia featuring long technical sections, limited aid stations, a 23 hour time limit, bus transport to the start, and packet pickup in Phoenicia.