The Naples Trail Day Challenge

JUN
26
2027
A free GPS tracked hill-loop challenge around Naples, NY supporting the Naples Trail Collective with multiple named climbs and an honor system combined time result.
Sat 26 Jun 2027

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About the race

The Naples Trail Day Challenge is a free, community event in support of the Naples Trail Collective, based at Engine 14 Brewery in Naples, NY. Participants complete a series of marked hill-loop courses during the day and record their progress on the GPS platform of their choice. Only loop times count toward results; there is no official timing and competitors report times on the honor system.

The athlete with the shortest combined loop time will be named the Great Big Winner. Safety and logistics notes are part of the event. Participants must check in at Engine 14 before heading to trails. Courses are marked, but participants are encouraged to bring maps and download GPX files.

There is no aid on course; participants are responsible for their own hydration and fuel and must provide their own transportation between course locations. Organizers recommend a charged cell phone and ask participants to follow rules of the road and basic social niceties. Running between all loops would be about 17 miles with 2,500 feet of elevation, an option organizers do not recommend. Course highlights include the Marty Dodge Climb starting at Naples Community Park and following the Twisted Branch Trail into the High Tor Wildlife Management Area with a descent via the Hatch Hill Trails.

The Demoralizer begins at Conklin's Gully and requires a creek crossing before a climb and downhill. The Great Hill and Clark Gully loop follows the route used by the former Great Hill Ultra and lies in an area associated with the Seneca Nation. Visit the organization's website for the most recent information.

Great Hill and Clark Gully
The Demoralizer
The Marty Dodge Climb
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