Route 66

It can be maddening to follow old Route 66 across St. Louis, but its many great spots—Ted Drewes Frozen Custard Stand, in particular—make it well worth the effort. One route crossed the Mississippi River right into downtown from Collinsville, Illinois, while another “City 66” route headed across the Chain of Rocks Bridge before running into downtown St. Louis along Florissant Avenue and Riverview Drive.

Heading southwest out of downtown, the old road followed Gravois Avenue, Chippewa Street, and Watson Road, just south of the parallel I-44 freeway.