Route 66

Cuba

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.

Rolla

Twenty miles west of Cuba, about midway between St. Louis and Springfield, one of the liveliest towns along the Ozark Mountains stretch of Route 66 is Rolla (pop. 20,075; pronounced “RAW-la”). In the center of town, right along old Route 66 on the campus of the Missouri University of Science and Technology (MUST), one big draw is the half-scale replica of that ancient Druidical observatory, Stonehenge, created in 1984 to show off the high-tech stone carving capabilities of MUST’s High Pressure Water Jet Lab.

Adding to the surprising mix of international flavors is another Rolla tradition: a wild and crazy St. Patrick’s Day party, held every year since 1908, during which students paint the streets of Rolla green, slay rubber snakes, and drink just about anything they can find, all in homage to the Emerald Isle.

Amongst the I-44 freeway clutter of Waffle Houses and Shoney’s at the west end of Rolla, there’s still a sign for the fireworks and moccasins on sale at the landmark Totem Pole Trading Post. Once you’ve got your fill of T-shirts and postcards, head up the hill to Rolla’s most popular watering hole, Rob and Kricket’s Tater Patch (103 Bridge School Rd., 573/368-3111). It’s on the south side of Route 66 across from the Rolla visitors center. Try one of their signature baked potatoes topped with pulled pork for a unique taste treat. They’ve also been serving big breakfasts, pork tenderloins, delicious onion rings, and ice-cold beer for more than 40 years. And anytime you’re near Rolla, make sure to set aside enough appetite and enough time to enjoy A Slice of Pie (601 Kingshighway St., 573/364-6203), on old Route 66 south of downtown, where two former schoolteachers bake an amazing array of fruit, nut, cream, and meringue pies, and even a few creamy quiches.