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Rolling west from Leasburg on Route 66 the old highway follows the gentle roll of the Ozark Mountains, courses through forests, and past Belmont Vineyard with its event center and restaurant perched high on a hill with a commanding view of the valley. Even though I-44 can often be seen through the trees, there is a sense of timelessness that sets the stage for your arrival in Cuba.

Missouri Hick, with its rustic façade, one of the best barbecue restaurants on Route 66, and its neighbor, the iconic Wagon Wheel Motel, the first businesses encountered in Cuba leave little doubt that this is a very special place. Dating to the mid 1930’s the Wagon Wheel Motel, and Connie’s Shoppe housed in the building that once served as a restaurant, is a true gem that is proclaimed to be the oldest continuously operated motel on Route 66. Renovated by Connie Echols, and her sister Riva, the motel is a delightful blending of the motel’s classic features and modern amenities. The rustic stone cabins in a park like setting that is tinged in a neon glow when the sun sets are a true roadside oasis and a revered destination for legions of Route 66 enthusiasts.  

For a village of less than 3,500 people Cuba is a surprising delight. The towns rich history is portrayed in an array of colorful murals that have led to Cuba recognition as Missouri’s “Mural City.” The diversity of restaurants and dining options is another surprise.

Shelley’s is a little hole in the wall diner located just down the hill from the Wagon Wheel Motel. Be prepared to rub elbows with the locals if you stop by for breakfast because the diminutive restaurant fills up quick in the mornings. The breakfast is simple, traditional American fare; biscuits and gravy, eggs, bacon and sausage, and thick black coffee.

At the intersection of Route 66, E. Washington Boulevard, and state highway 19, North Franklin Street is the FourWay restaurant. The former gas station and garage complex that dates to the early 1930’s is an excellent example of how to re-purpose an historic building. The diverse menu is a real treat with authentic Mediterranean cuisine being the restaurants specialty. Also offered are vegan and gluten free options, and unique offerings that blend the traditional with the European influence.

Tuggie & Joe’s is an excellent option for breakfast, lunch and dinner if the palate prefers hearty and traditional American dishes. Rivera Maya offers excellent traditional Mexican foods that would be welcome with aficionados in New Mexico. Frisco’s Grill & Pub is another surprise. This charming restaurant is worthy a much larger city. Then there is the Rockfair Tavern, an authentic 1930’s roadhouse that seems suspended in time.

Dining options are but one of the surprises awaiting discovery in Cuba. Nestled in the scenic Ozark Mountains, Cuba is more than just a stop for Route 66 enthusiasts, it is an almost magical place that seamlessly blends a modern industrial park with preservation that presents the illusion time has stood still for decades.  (See our dining map here)

  Written by Author and Historian Jim Hinckley of Jim Hinckley’s America