Trail Running Calendar New York 2026-2027

An obstacle course backyard ultra where athletes run an approximately 3 miles loop every hour until one remains. Solo and relay formats are available, with a 50 mile solo option and team relays for groups of three to six.

A 3.1 miles moonlight trail run at Lakeside Park in Pawling, NY with varied terrain, glow markers, required personal light, post run towel and a handmade finisher medal. Proceeds support the Pawling Recreation Department.

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..

A trail event at Red Wing Recreation Area on July 5, 2026, offering 15K, 30K, and 60K options across a 15k loop with mixed terrain, on-course aid stations, post-race food, and awards for top finishers.

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 half marathon and marathon in Naples NY starting and finishing at Naples Community Park. The course runs through downtown and High Tor Wildlife Management Area with multiple aid stations and a two loop marathon option.

A 5K obstacle mud run in Albany on July 12, 2026 at Harley Rendezvous Classic Inc. The event offers standard and VIP ticket options with race items, rinse stations, and photos, and donates to the National Breast Cancer Foundation.

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 winery-based running event on July 18, 2026 at Liberty Vineyards offering a 1K tasting walk and a 5K run/walk, with tastings, a finish-line wine, event shirt, on-site food, music, and post-race activities.

A 55K self-supported trail ultramarathon in New York's Adirondack Park along the Northville Placid Trail. Technical terrain with about 3,300 feet of gain; registration requires a qualifying race and includes a shirt and two meals.