Pedal the Gap-Pinnacle Challenge

Pedal the Gap offers five route options, from a beginner-friendly 20-mile ride to the challenging 77-mile Pinnacle route. Cyclists choosing the 55- or 77-mile courses travel through the one-mile Cumberland Gap Tunnel into Cumberland Gap National Historical Park, where they begin the iconic 3.1-mile climb to the Pinnacle Overlook, averaging a 6.6% grade. After conquering steep switchbacks, riders are rewarded with spectacular views of Kentucky, Tennessee, and Virginia.

This climb follows a corridor rich in American history. In 1775, Daniel Boone blazed the Wilderness Road through the Cumberland Gap, opening the gateway to westward expansion. An estimated 200,000–300,000 settlers passed through this passage, and historians believe that nearly 30% of Americans living west of the Mississippi today can trace their ancestry through the Gap. The Pedal the Gap–Pinnacle Challenge brings that remarkable migration story to life—on two wheels.