Route 66

Along I-44 west of Meramec Caverns, the old Route 66 roadside is lined by ramshackle wooden stands, which, toward the end of summer, sell sweet Concord grapes from local Rosati vineyards. The stands are located along the frontage roads (which in many cases are the remnants of the original Route 66), but people park along the freeway and walk to them. At the eastern edge of this grape-growing district, the small town of Cuba has a vintage Phillips 66 gas station and a dozen colorful murals covering large areas of downtown buildings with scenes from Cuba’s history, depicting everything from the Civil War to the day in 1928 when Amelia Earhart made an emergency landing in a farmer’s field.

Cuba also makes it onto many Route 66 itineraries thanks to the friendly Wagon Wheel Motel (901 E. Washington St., 573/885-3411, $66 and up), which for many years was famous for offering 1930s charm at 1970s prices. Although it has been remodeled, the Wagon Wheel still allows travelers to sample a kinder, gentler, less complicated era—even while taking advantage of clean comfy beds and free Wi-Fi. The Wagon Wheel Motel is right on Route 66. An added bonus: good barbecue is right next door at the Missouri Hick BBQ (573/885-6791).

The route west from Cuba to Rolla, along what’s now marked as Hwy-ZZ, offers a fine stretch of unsullied Route 66 scenery, made all the more enticing by the presence of the World’s Largest Rocker, a Guinness-sanctioned champion chair (not a musician!) standing more than 40-feet tall, four miles west of Cuba outside the Fanning Outpost souvenir stand and archery supply store.