Pedal the Gap – Cumberland Gap, TN 2026

Pedal the Gap is a first year cycling event, with the staging point the historic town of Cumberland Gap, TN. Five route distance options are offered, ranging from the beginner friendly 20 miler up to the 77 mile route that includes the famous Pinnacle climb. Those choosing the Pinnacle (77 or 55 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 77 or 55 miles. Cyclists choosing NOT to do the challenging Pinnacle climb will have options of 25, 40, or 62 miles, all starting in Cumberland Gap and all totally located in TN,