The Naples Trail Day Challenge

JUN
26
2027
A free Naples Trail Day challenge of marked hill-climb loops around Naples with GPS-based times and a gathering at Engine 14 Brewery.
Sat 26 Jun 2027

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The Naples Trail Day Challenge

This event supports the Naples Trail Collective and features a series of marked hill-climb loops around the Naples area. Participants complete the loops during the day and record their progress on a GPS platform. At the end of the day participants gather at Engine 14 Brewery to refuel, compare times, and share stories. The athlete with the shortest combined time for the loops will be named the Great Big Winner.

Courses described for the challenge include several local climbs and trail sections. The Marty Dodge Climb begins at Naples Community Park and follows the route used by the Twisted Branch Trail Run into the High Tor Wildlife Management Area, ending at the Finger Lakes Trail intersection before a descent via the Hatch Hill Trails. The Demoralizer begins at Conklin's Gully parking and requires a creek crossing to start the climb, then follows a connector trail to the downhill section. Great Hill and Clark Gully are noted for their cultural history with the Seneca Nation; one leg follows the course used by the Great Hill Ultra.

Practical details are stated plainly: the event is free and donations to the Naples Trail Collective are welcome; courses are marked but participants are advised to bring maps and GPX files; there is no aid on course so participants must carry their own hydration and fuel; check-in at Engine 14 is required before heading out. Traveling between loops by foot would be about 17 miles with 2,500 feet of elevation, though that option is not recommended by organizers. Visit the organization's website for the most recent information.

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