Pedal the Gap is a first year cycling event, with the staging point the historic town of Cumberland Gap, TN. Six route distance options are offered, ranging from the beginner friendly 20 miler up to the 80 mile route that includes the famous Pinnacle climb. Those choosing the Pinnacle (80 or 50 mile options) will enter Kentucky through the mile long Cumberland Gap tunnel to Cumberland Gap National Park, where they will start the 3.1 mile/6.6 % "classic mountain" climb to the famous Pinnacle overlook. After conquering the double digit grade switchbacks, cyclists are treated to breathtaking views of Kentucky, Tennessee, and Virginia.
After climbing the Pinnacle, cyclists will travel back through the tunnel into TN, and can choose from two flat to rolling loops that will give them a total ride distance of either 80 or 50 miles.
Cyclists choosing NOT to do the challenging Pinnacle climb will have options of 20, 35, or 65 miles, all starting in Cumberland Gap and all totally located in TN, with rolling to flat terrain and no major climbs. Three rest stop locations will provide support for all routes, not including the 20 mile option. Race Day Events will provide course marking and SAG support for all routes.
Ride logo shirts and a post ride meal at Angelo's in the Gap (including one free beer) highlight the event swag.
Aug 15, 2026
Distance — 50 Miles
Type — —
07:00
$60.00
These values represent the 3-year monthly averages for August in Cumberland Gap.
Learn more about the host city, Cumberland Gap.
Cumberland Gap is a town in Claiborne County, Tennessee, United States. Its population was 313 at the 2020 census, and estimated to be 315 in 2023. The town is located below the Cumberland Gap, a historic mountain pass for which is the town's namesake, and inside of the boundaries of Cumberland Gap National Historical Park.
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location_on Sneedville, Tennessee, US
calendar_today Aug 05, 2026
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