Trail Running Calendar New York 2026-2027

A scenic 5K on vineyard trails at Sheldrake Point Winery with chip timing and a non-timed 1 mile walk that includes a wine ticket and souvenir bib; post-event wine service and live music create a relaxed finish area.

Experience a unique trail race through the Westmoreland Sanctuary where you choose your own path at the fork. Start and finish at Fox Lane High School for a memorable 5k adventure in Bedford.

A 10K+ trail race at Buttermilk Falls State Park near Ithaca featuring varied trails, a long steep climb and fast descent, plus a free 1-mile kids fun run and age-group awards; online registration required.

Free community trail run and afterparty in Victor with HOKA Speedgoat 7 demos, a 3 to 6 mile Seneca Trail run or hike, and an indoor viewing party of the Western States 100 Golden Hour with refreshments.

Mountain races on Whiteface Mountain with one- and two-loop courses, a steep Vertical K ascent, aid stations, a kids ascent, and an optional combined entry for large daily elevation totals.

Trail ultramarathon in the Finger Lakes National Forest offering 25K, 50K and 50 mile options on a 16.5 mile loop. The course features singletrack, grassy pastures with cows, dirt roads, about 1,300 feet of climb per loop and six aid statio..

Trail races of 60K, 30K and 15K take place at Red Wing Recreation Area in Lagrangeville NY. The 60K is four laps of a 15K loop with about 6500 ft of climb and on-course aid stations and post race food.

Part of the Shawangunk Runners summer series, this week features a 4.7 mile Undercliff Overcliff loop plus kid races, held at Trapps Bridge with parking at Mohonk Preserve West Trapps and no registration fee.

A multi-event trail running series at Chestnut Ridge Park in July and August where each runner's six best times from eight races count toward series awards; individual weekly walk-up registration is available alongside full series pre-regis..

Experience a unique four mile trail race through the historic Forest Park in Queens. Run along naturally carved glacial terrain and pine groves with your dog to support a local animal rescue organization.

Trail running event in Naples, NY on July 11, 2026 offering a half marathon loop and a marathon by doing two loops. The route runs from Naples Community Park through downtown and the High Tor Wildlife Management Area with aid stations.

A women only 5K obstacle mud run in Albany, NY on July 12, 2026 featuring more than 18 obstacles. The event welcomes participants aged seven and up and is presented as non competitive with an emphasis on fun and teamwork.

Trail races at Watkins Glen International on July 12, 2026 feature a 3 mile course available as an individual race or as a three person relay, plus a 1.5 mile family course with proceeds supporting a wellness center.

Experience a midweek evening trail run through the diverse terrain of Bowdoin Park. This 5 mile race features a mix of grass and rocky trails with awards for top finishers and a food drive for the local pantry.

Timed 12 hour and 24 hour ultraruns plus 12 hour and 24 hour relay options on a mostly paved one mile loop at Rochester Rotary Sunshine Camp, with a staffed aid station, flexible relay rules, and an optional personalized bib.

Run along the scenic Minnesetah River in Penn Yan featuring historic mills and waterfalls. This trail event offers half marathon and 10K distances with a festive post race party at the local Moose Lodge.

A wine-themed event at Liberty Vineyards on July 18, 2026 featuring a 1K tasting walk and a 5K run and walk, sampling stations, finish-line wine, and on-site food, music, and contests.

A remote, self-supported 55K on the Northville Placid Trail in the Adirondacks with technical singletrack and about 3,300 ft of gain. Registration includes a shirt, swag, and two meals; a recent validating race result is required.

A single day endurance walk on Gore Mountain near North Creek, NY offering 7, 14, 21 and 28 mile loop options with a 10 hour finish window. The shaded route climbs wooded slopes and ridge roads with aid stations, timing, and finish rewards.

Part of the Shawangunk Runners summer series since 1974, the Blueberry Run in Kerhonkson features a 4.1 mile loop around Lake Minnewaska plus shorter kids races, with parking at Minnewaska State Park and no registration fee.