Route 66

The largest city in southern Missouri, Springfield (pop. 167,319) doesn’t feel nearly as big as it is, though it does sprawl for many miles in all directions. Despite the ongoing growth and development, most notably the green and pleasant Jordan Valley Park surrounding the attractive downtown baseball stadium and sports complex, Springfield has preserved much of its old Route 66 frontage, along St. Louis Street east of downtown, as well as the grandly named Chestnut Expressway west of downtown. The 20-mph speed limit on downtown streets—along with tons of free parking—enables Route 66 pilgrims to pay homage to the town’s Arabesque landmark Shrine Mosque theater (601 E. Saint Louis St., 417/869-9164), which still hosts occasional concerts.

Springfield is also celebrated as the place where “Wild Bill” Hickok killed fellow gambler Dave Tutt, apparently because Tutt wore the watch he’d won from Hickok playing cards. A plaque in the central square, just west of the Shrine Mosque, tells one of many variations on the tale.

Springfield has at least one fine old Route 66 motel: the Route 66 Rail Haven (203 S. Glenstone Ave., 417/866-1963 or 800/670-7234, $79 and up), on the corner of old Route 66 and US-65. Open since 1938, it has been fully modernized and now is a Best Western affiliate with a railroad theme. A mile away on old Route 66 is one of the earliest and most stylish models of the Steak ’n Shake burger chain (1158 St. Louis St., 417/866-6109, daily 24 hours). This is one of the last ones where carhops still bring your food to your car (during daylight hours).