Trail Running Calendar New York 2026-2027

Explore the scenic trails of Monroe County during this four part mid week race series. Enjoy chip timed runs through various local parks along with post race cookouts and custom series participant awards.

An obstacle course Last Man Standing event in Binghamton on June 27–28, 2026 where athletes run roughly 3 mile loops each hour until one remains. Relay teams of 3 to 6 complete either 12 or 24 hours as a team.

Experience a scenic 5K run through the 200 acre Sheldrake Point Winery featuring cross country trails and views of Cayuga Lake followed by live music and wine.

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 trail race at Buttermilk Falls State Park featuring a 10K plus loop of varied terrain and a long steep climb. A free, noncompetitive 1 mile kids run is held alongside the main race.

Multiple mountain races on Whiteface Mountain near Wilmington, NY featuring very steep climbs and heavy descents; options include Mountain Race, Sky Race, Vertical K, Vert Junky, and Kids Ascent.

Finger Lakes 50s on July 4, 2026 features 50 mile, 50K and 25K trail races on a 16.5 mile loop in Finger Lakes National Forest near Hector, NY. The course mixes single track, pastures and roads and has four aid stations.

Trail races at Red Wing Recreation Area near Lagrangeville NY offering 60K, 30k and 15K on a 15k loop with varied terrain, aid stations, and awards for top finishers and finishers in select distances.

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.

This trail run in Naples, NY explores the scenic High-Tor Wildlife Management Area. The course starts in the community park, features significant climbs on the Finger Lakes Trail, and passes multiple aid stations. Runners can choose between..

Muddy Princess Albany is a 5 km obstacle mud run for women held at Harley Rendezvous Classic Inc. Join this non competitive event focused on unity and empowerment while supporting the fight against breast cancer.

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.

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.

Wicked Wine Run in Buffalo, NY combines a 5K run or walk with a 1K tasting walk at Liberty Vineyards & Winery on July 18, 2026, offering wine tastings, event shirts, bibs, finisher items, on-site food and entertainment.

A remote 55K ultra on the Northville Placid Trail between Piseco Lake and Wakely Dam in the Adirondacks. The self supported technical trail gains about 3300 feet and requires a recent validating race for registration.

Choose your distance from 7 to 28 miles in this Adirondack endurance walking event at Gore Mountain. Hike through shaded forests and along scenic ridgelines with the option to add weight for a rucking challenge.

Explore the scenic trails of Monroe County during this four part mid week race series. Enjoy chip timed runs through various local parks along with post race cookouts and custom series participant awards.

The Webster Trail Classic is a scenic trail run through three distinct parks in Webster, NY. Runners can choose between a 10-mile or a 3.5-mile course, each offering varied terrain. A free kids fun run is also part of the event.

A two-day trail running festival on July 25 and 26, 2026 with ultramarathon, shorter distance and relay options around Mendon Ponds. Proceeds support the Blue Foundation.

This backyard ultra challenges runners to complete a 4.167-mile loop each hour on Mt. Hovenberg's trails. Participants set their own distance goals, and the last person standing wins. The event supports Team RWB and is capped at 200 runners..