1
St. Clair, MO to St. Louis, MO
61.5 miles: 1 hours, 53 minutes
Courtesy of Missouri Botanical Garden
After leaving St. Clair, you won't spend much time on I-44 before reaching the outer St. Louis suburbs. En route on old Route 66 is the site of Times Beach, founded in the 1920s as a Meramec River resort. A toxic waste contamination in the early 1980s rendered the town uninhabitable; the pollution was cleaned up and today the area is Route 66 State Park.
2
St. Louis, MO to Edwardsville, IL
26.8 miles: 1 hours, 11 minutes
Getty Images / Jeremy Woodhouse
Following old Route 66 through St. Louis can be maddening, since several streets have a “66” connection. Historic Chain of Rocks Bridge—now a mile-long hiking and biking trail just south of I-270—was the former Mississippi River crossing point. Don’t leave St. Louis without visiting The Arch, symbolic “gateway to the West.”