Trail Running calendar near Watertown 2026-2027

An informal 6 km trail run on Sugarbush Vineyards' private trails as part of the Friday Night Happy Hour series, with cupless policy, water at start/finish, manual timing and on-site registration options.

A community trail run and walk in Holland Patent raising funds for autism awareness and local clubs, featuring a 5-mile trail option and a free kids 1K, with water stations, timing, and donated socks for early participants.

A day of timed endurance challenges on a wooded 2.62 mile loop at Tilden Hill Farm in Verona NY. Events finish with an optional pond plunge and a post event celebration with medals and awards.

The Last Hour is the final Happy Hour Friday Night Series race, an 8 km trail run at Vanderwater Conservation Area featuring pine groves, boulder fields and riverside trails. No aid stations; parking fees apply.

A backyard ultra at Winona State Forest near Mannsville, NY, run on repeating 4.167 mile loops that start each hour. Runners continue hourly laps until one runner completes the final lap and is the last runner standing.

Green Lakes Endurance Runs in Fayetteville, NY offers 100K, 50K, 25K and a 12 hour timed race on varied trails around Green and Round Lakes, with staffed aid stations and looped courses starting and finishing at Tulip Hill Picnic Area.

A women only back yard ultra on a 4.167 mile loop run every hour on the hour in Phoenix NY. Forest trails, open field sections and night running combine with common ultra distance milestones and proceeds benefiting local women's shelters.

Experience an outdoor adventure at Everest Park featuring a four mile obstacle course with forty natural and man made challenges. Families can choose between the full mud run or a specialized mini course for younger children.

An obstacle and fitness race on September 13, 2026 in Fayetteville, NY featuring a roughly 3 mile course with about 23 first responder inspired challenges, including Search & Rescue, Hose Drag and timed mental focus tasks.

Ultrarunning event at Sugarbush Vineyards and Winery offering solo 6, 12 and 24 hour options, a 24 hour relay and a 12 hour evening race on an approx 3 km loop.

A 5K cross country race at Pine Grove Middle School in East Syracuse on 19 September 2026, run on a varsity XC course with mostly trails and grass; registration runs from March 7 to September 18, 2026.

A closed cross country event on Fort Henry Hill featuring a 5K on a 2.5 km grass loop and a separate 1 km kids race. Team scoring and age-category medals are included, with early 5K registrant swag and finish ribbons for kids.

A community memorial run in Hinckley, NY offering an in-person five-mile trail run/walk, a virtual five-mile option, and a kids fun run; proceeds support a memorial scholarship for students pursuing medical training.

A charity running event at Green Lakes State Park on September 20, 2026 with 8K and 5K races, a free kids fun run, a 5K lake trail route, and a 2 Mile trail walk, plus shirts, awards, aid stations, and free ice cream.

The Morgan Hill Trail Races will take place in Fabius on Sunday 27 September 2026.

A 3.1 mile trail race at the Great Swamp Conservancy habitat center in Canastota NY on October 4, 2026. The course runs on natural trails and crosses a country road; registration opens July 15 and the fee is $20.

A fall trail 5K in Winona Forest that supports Friends Forever Animal Rescue, featuring an all-off-pavement course, on-site timing, awards, a post-race BBQ, and the option to add a donation during registration.

Experience the wilderness trails of Deerfield Town Park with a variety of trail races for all ages. Enjoy a professionally timed 5K or a community run while supporting the local food pantry in your favorite running costume.

The MT Adventures Trail Run Series will take place in Kingston on Sunday 25 October 2026. You can run between 8 and 21 kilometers.

A third annual Veteran's Day 5k trail run at Clear Path for Veterans in Chittenango, NY, featuring peaceful trails and wide views to the Adirondack foothills. The event supports Clear Path's programs for veterans and their families.