Riding 1,200 Miles Just to START Route 66

Before starting Route 66, I had to get to Chicago first! In this video, I take on a solo multi-day motorcycle run covering over 1,200 miles from Jacksonville, Florida to Chicago, Illinois. From battling heavy mountain downpours across the Blue Ridge to detours through Kentucky, Ohio, and Indiana, here is the full journey leading up to the official start of the Mother Road. 📍 Route & Stops Covered: Day 1: Jacksonville, FL ➡️ Knoxville, TN (600 miles through heavy rain) Day 2: Knoxville, TN ➡️ Sturgis, MI ➡️ South Bend, IN (500+ miles) Day 3: South Bend, IN ➡️ Chicago, IL (Final stretch to the Route 66 starting point) 🏍️ What to Expect: Long-distance motorcycle touring tips & dealing with summer storms Harley-Davidson dealership visits & scenic backroads The buildup to riding Route 66 end-to-end