The Naples Hill Challenge
Sat, Jun 27
|Engine 14 Brewery
Free Event


Time & Location
Jun 27, 2026, 9:00 AM – 1:00 PM
Engine 14 Brewery, 52 West Ave, Naples, NY 14512, USA
About the event
Description
To help celebrate Naples Trail Day, we're offering a unique challenge showcasing some of the most iconic hill climbs in the Naples area. During the day, participants will complete these loops, recording their progress on the GPS platform of their choice. At the end of the day we'll gather at Engine 14 Brewery to refuel, compare times, and share stories. The athlete with the shortest combined time for the loops will be crowned the Great Big Winner!
Schedule
9:00 AM - Gather at Engine 14 to check-in.
9:15 AM - Start of the event.
12:00 PM to 1:00 PM - Return to Engine 14.
Registration
This is a free event, although donations to the Naples Trail Collective are highly appreciated and will be used to improve the trails you'll be using.
You do not need to RSVP, but we will use that information to send updates about the event.
For safety reasons, participants will need to check-in at Engine 14 before you head out on the trails so that we know who is out there.
General Guidelines
Each of the courses will be marked, but we encourage participants to bring maps and download GPX files of the route.
Participants are encouraged to bring a charged cell phone with the number for the event organizers.
There is no aid out on course, so participants are responsible for any hydration and fuel they will need.
Participants need to provide their own transportation to the courses. For the highly adventurous, continuously running the full loop would be around 20 miles. The event organizers do not recommend this option.
Participants need to follow the rules of the road when traveling between locations and when parking.
Determining the order of the loops and the amount of break between loops is up to the participant. Only the time of the loops is counted towards the results.
There is no official event timing. Participants will be on the honor system to provide times for their loops. Ideally this would be with a GPS map that confirms completion of the course.
Participants need to follow the rules of social niceties with fellow participants, other trail users, and event organizers.
Courses
The Marty Dodge Climb will start at the Naples Community Park, which has ample parking. The climb portion of the loop follows the path the Twisted Branch Trail Run takes to enter the High Tor Wildlife Management Area. Reaching the intersection with the Finger Lakes Trail will mark the end of the climb, and a gradual descent back to the park. The descent will feature the Hatch Hill Trails, which are a focus of the Naples Trails Collective's Master Plan. Early phases of the project are already in motion, with the goal of increased access, sustainability, and easier maintenance of this trail corridor connecting Naples to High Tor.
The Demoralizer starts in the parking area for Conklin's Gully. Participants will need to cross the creek to start the climb, which will be familiar to anyone who has subjected themselves to the Spring Classic Muddy Sneaker Trail Race. Once reaching the top of the climb, the course will mostly plateau as it takes a connector trail to the downhill portion of the course. The Gully is an amazing spot to creek-walk and explore the many waterfalls, but today is not the day for leisurely strolling.
Great Hill and Clark Gully are revered as the birthplace of the Seneca Nation, also known as Onöndowa'ga:' or "People of the Great Hill." To learn more about the history and culture of the area, we recommend a visit to the Seneca Art & Culture Center at Ganondagan.
The route for this leg of the challenge follows the course taken by the gone-too-soon Great Hill Ultra. The loop was no doubt a memorable challenge starting at mile 50 of the 100km race.






