Route 66, part one: Chicago to Oklahoma City

Route description

Start in downtown Chicago at the Route 66 Begin sign on Adams Street, mile zero of the old highway, and follow the brown historic-route signs southwest out of the city. Traffic eases beyond Joliet, and at Wilmington the Gemini Giant, a 30-foot fiberglass spaceman holding a rocket, stands beside the road. From there the route crosses flat Illinois farmland, mostly alongside I-55, to the state capital, Springfield.

At St. Louis the Old Chain of Rocks Bridge crosses the Mississippi with a 22-degree bend in the middle; it is open only to walkers and cyclists, so park and walk out onto it. In the city, Ted Drewes on Chippewa Street has served frozen custard since 1941, and a “concrete” is the thing to order. Southwest of St. Louis the land starts to roll into the Ozarks, and Meramec Caverns at Stanton runs guided tours through multi-level limestone caves.

The old road follows I-44 across Missouri to Joplin, clips the corner of Kansas for a few miles and enters Oklahoma. Near Tulsa, the Blue Whale of Catoosa sits in a spring-fed pond beside Route 66, a good place to stretch your legs. West of Tulsa the two-lane alignment runs through small towns roughly parallel to the Turner Turnpike, a toll road you can use if you are short of time.

At Arcadia, the restored 1898 Round Barn and the 66-foot neon soda bottle of Pops 66 Soda Ranch are a short drive apart, and Pops is at its best lit up at dusk. Oklahoma City is less than an hour further on. In towns the historic alignment changes often, so a turn-by-turn Route 66 guide or app saves a lot of backtracking; spring and fall are the most comfortable seasons, and large motorhomes will find parking easier outside central Chicago and St. Louis.