Route 66

If you have the time and the inclination to stretch your legs and breath deeply, make your way to the northeast edge of St. Louis, where instead of following the 75-mph I-270 freeway, you can cross the Mississippi between Illinois and Missouri on the historic Chain of Rocks Bridge. The bridge has been renovated for use as a mile-long bike and hiking trail (314/416-9930, daily dawn-dusk), decorated with an array of old gas pumps and signs, just south of the modern I-270 freeway. If you’re driving, the best parking is on the Illinois side of the bridge, but cyclists or energetic walkers can cross the surprisingly narrow bridge and continue all the way to the Gateway Arch in St. Louis, following an 11-mile Riverfront Trail that snakes between the flood walls, the river, and acres of heavy (and sometimes smelly) industry.

Not quite on the same scale as the Cahokia Mounds, the Chain of Rocks Bridge, or even the Collinsville catsup bottle, the nearby Route 66 town of Mitchell holds one more Route 66 landmark: Luna Café (201 E. Chain of Rocks Rd., 618/931-3152), a one-time casino, speakeasy, and brothel built in 1924 that’s now a pretty seedy but atmospheric bar, north of the I-270 freeway exit 6, along old Route 66.