The Naples Trail Day Challenge

JUN
26
2027
A free GPS based hill loop challenge in Naples NY supporting the Naples Trail Collective with marked courses and a post run gathering at Engine 14 Brewery.
Sat 26 Jun 2027

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The Naples Trail Day Challenge

The Naples Trail Day Challenge is a free event held in support of the Naples Trail Collective and centered on a series of marked hill loop courses in and around Naples, New York. Participants complete the loops during the day, record their progress on the GPS platform of their choice, and gather at Engine 14 Brewery to refuel, compare times, and share results. The participant with the shortest combined time for the loops is declared the Great Big Winner.

For safety participants must check in at Engine 14 before heading to the trails. Courses will be marked, but participants are encouraged to bring maps and download GPX files. There is no aid on course, so participants are responsible for their own hydration and fuel and are advised to carry a charged cell phone. Transportation between course locations is the responsibility of each participant. Traveling between all loops on foot totals about 17 miles with 2,500 feet of elevation, an option the organizers do not recommend. Only the timed portions of each loop count toward results, and timing is conducted on the honor system with GPS confirmation preferred.

Course highlights include the Marty Dodge Climb starting at Naples Community Park and following the Twisted Branch Trail toward the High Tor Wildlife Management Area, the Demoralizer beginning at Conklin's Gully with a creek crossing and waterfall features, and the Great Hill and Clark Gully route, noted for its cultural significance to the Seneca Nation and its relation to the former Great Hill Ultra. Visit the organization's website for the most recent information.

Great Hill and Clark Gully Loop
Marty Dodge Climb Loop
The Demoralizer Loop
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