The Naples Trail Day Challenge

JUN
26
2027
A free, self supported hill climb challenge in Naples NY where participants complete marked loops, log times with GPS, and compare combined results 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 in support of the Naples Trail Collective, centered at Engine 14 Brewery in Naples, New York. Participants complete a series of marked hill-climb loops in the Naples area, record their progress on a GPS platform, and reconvene at Engine 14 to compare times. The athlete with the shortest combined time for the loops is recognized as the overall winner.

Courses include named climbs and loops with local access points and parking. The Marty Dodge Climb begins at Naples Community Park, follows the Twisted Branch Trail into the High Tor Wildlife Management Area, ends at the Finger Lakes Trail intersection, and returns via Hatch Hill Trails. The Demoralizer starts at Conklin's Gully parking, requires a creek crossing at the outset, then follows a plateau and connector trail into a downhill section that passes waterfalls. The Great Hill and Clark Gully leg follows the route of the former Great Hill Ultra and traverses terrain associated with the Seneca Nation.

Event guidelines note that courses are marked and GPX files are available, but there is no aid on course. Participants must check in at Engine 14 before heading out, provide their own transportation, carry their own hydration and fuel, and follow rules of the road when traveling between locations. Only loop times count toward results; there is no official timing and participants report times on the honor system. Running between loops would total about 17 miles with 2,500 feet of elevation. Donations to the Naples Trail Collective are appreciated and will be used to improve the trails used in the event. Visit the organization's website for the most recent information.

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

Events nearby

Hopson Trail Runs in Honeoye offers scenic fall trail routes of 5K and 9K through WoodsEdge Retreat and Sandy Bottom Park. The event supports Embrace Your Sisters and includes a post race gathering at Birdhouse Brewery with music and a complimentary..
Trail runs at Hunt Hollow in Naples NY on 10/18/2026 include a 5.8K mountain course and a 3.1K family run, followed by a family-friendly festival with music and activities.
Winter trail run at Harriet Hollister Spencer State Recreation Area on January 9, 2027, an approximately 10k loop and the first race of the Common Ground Winter Trail Series.
Winter trail race at Ontario County Park with one to three 4 mile loops, an added snowshoe option, and post-race pancakes and warm drinks.
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