Trail Running calendar near Henrietta 2026-2027

A chip timed 5K through Sheldrake Point Winery with vineyard trails and Cayuga Lake views, a tech shirt and stemless wine glass for participants, age based awards, and a complimentary glass of wine for finishers 21 and over.

A trail race at Buttermilk Falls State Park featuring a 10K plus course with varied terrain, a steep climb and fast downhill finish, plus a free untimed 1 mile kids fun run.

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 night trail race at Batawa Ski Hill on July 11, 2026, with marked 7 km and 14 km courses. Headlamps are required, headphones are not allowed, and aid stations provide water and nutrition.

A community organized trail race in Naples, NY featuring a half marathon loop with an option to run a marathon by doing two loops, varied terrain through High-Tor Wildlife Management Area and downtown, and multiple staffed aid stations.

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 5K trail run at Bella Rose Vineyard in Lewiston, NY on July 19, 2026 offering a stemless wine glass and complimentary wine tasting for those 21 and older, professional timing, post-race snacks, and vineyard views.

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.

A community focused trail run at Sugarbush Vineyards in Prince Edward County, with an approximately 6 km flat course on private trails. The event is cupless, offers water at start and finish, manual timing and on site registration.

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 in Mendon Ponds on July 25 to 26 2026 offering solo races from 5 mile to 100 mile plus 99 mile and 50 mile relays, with camping, aid stations, volunteer requirements, and proceeds benefiting the Blue Foundat..

Trail races in Kennedy State Forest near Virgil, NY offering 15K and 7K courses on marked single track, logging and dirt roads with stream crossings, significant climbs, and nearby primitive camping at Hauck Hill.

Experience an intense mountain trail race at Swain Ski Resort featuring 2500 feet of elevation gain across two loops. This USATF Niagara Championship event tests runners with steep ski slope climbs and rapid descents.

Amer's Epilepsy Trail Race at Mendon Ponds Park offers timed 5K and 10K trail races plus an untimed one mile fun run. Walkers and leashed dogs are welcome and proceeds benefit EPI epilepsy programs.

An evening trail race at Fillmore Glen State Park offering 3-mile and 8-mile courses that run along the gorge rims and cross the creek on bridges. The marked routes include stairs, water stops, and count toward FLRC trail-circuit standings.

Beast of Burden Summer in Lockport NY follows the Erie Canal towpath and offers 100 mile, 50 mile and 25 mile distances with fully stocked aid stations and a start at Wide Waters Marina.

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.

A point to point 100K in Naples, NY on the historic Bristol Hills Branch trail through the Finger Lakes. Mostly single track with rugged terrain and a 20 hour cutoff; finishers earn four UTMB points and it is a Western States qualifier unde..

Test your endurance at this unique trail race in Tully where the coin toss determines your path. Complete as many loops as possible in three hours while alternating directions to stay on your toes.