Trail Running Calendar New York 2026-2027

A four-race 5K trail series in Cole's Woods, Glens Falls, held Tuesdays in May. Runners who complete all four races form a 20K challenge and compete for overall awards and raffle prizes.

A budget-friendly midweek trail series across four Monroe County parks offering single-race entries or an all four series option. Features chip timing, a post-race cookout, series scoring and awards plus a custom hat for series entrants.

Six 5K cross country races take place at Van Cortlandt Park from May 28 to July 30, 2026, on the classic Tortoise and Hare course. The final three evenings include free half mile kids runs, weekly awards and post race raffles.

Cayuga Trails in Ithaca, NY is a primarily singletrack race featuring waterfalls, stone stairs, and two distances, a 50 mile and a 50K. The race has a 440 runner cap, drop bag service, post-race gear, and charity support.

Trail run in Boutwell Hill State Forest near Cherry Creek New York offering 6k, 12k, 26k and 52k routes. The event raises funds for the Chautauqua County Equestrian Trail System and includes aid stations for the longer distances.

ENDURE Last Man Standing in Bethpage State Park asks runners to repeat a fixed 4.2 mile loop each hour; finish within the hour to continue. Laps continue with progressively shorter cutoffs until one runner remains or the event window ends.

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.

A two day family obstacle event at Obstacle Wonderland in Wallkill featuring adult sprint and multi lap endurance formats, plus kids 50 m and 1 km courses, finisher medals, podium awards, and a charity presence.

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.

A running event in Granville on May 30, 2026: a relatively flat 5k along the rail trail finishing on the footbridge over the Mettowee, plus a kids 1k. Registration opens March 26; 5k fee $25, kids run free.

Trail running in Ithaca, NY with a Half Marathon, a 6.66 Miler and a 5K on park trails. The looped course uses the Rim Trail, Gorge Trail, Red Pine and Finger Lakes Trail and includes park entry, a shirt and post race food.

A four-week, 90-minute trail running series for runners comfortable with about 3 miles. Sessions cover warm-ups, guided runs, hill and footwork drills, gear and safety, and include trail socks and gifts.

A weekly Thursday evening trail run and mountain bike race series at Mt Van Hoevenberg, held June through August, with age divisions, set distances, weekly raffles and series awards.

Trail runs in Naples NY with a rugged 25K single loop around the Cumming Nature Center and Honeoye Inlet Wildlife Management Area and a more runnable 10K. Proceeds support environmental education at the RMSC Cumming Nature Center.

A road and trail event at Rockwood Hall in Rockefeller State Park Preserve featuring a 10K and a 1K kids race. The course follows wide carriage roads with Hudson River views and wooded sections, and proceeds support carriage road maintenanc..

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.

A Spartan obstacle race weekend at Bethel Woods on June 6-7, 2026 featuring Sprint, Super and Kids races, an obstacle workshop, on-site camping, and team entry options.

A farm-based ultrarun on 06/06/2026 at Fish's Farm Market in Shortsville, NY where participants run or walk as many 1.52-mile loops as they wish. Timing, aid station, medals, prizes and raffles; proceeds benefit Colony Caregivers.

On June 6, 2026 at Rockland Lake State Park, the event offers a scenic 5K paved loop with a wheelchair division and a rugged 10K mountain run climbing 1,300 ft on technical trails.

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.