This inaugural cycling event launches from the historic town of Cumberland Gap, TN, with five route options catering to all fitness levels—from a beginner-friendly 20 miles up to an ambitious 77-mile route. The longer distances feature the iconic Pinnacle climb, a challenging 3.1-mile ascent with grades exceeding 10% that takes you through Kentucky's Cumberland Gap tunnel and rewards you with stunning panoramic views of three states before rolling back through Tennessee on easier terrain. If you prefer to skip the big climb, you can still choose from 25, 40, or 62-mile routes that start right in Cumberland Gap.