Bob’s Gasoline Alley in Cuba, Missouri, by Kathy Alexander.
Cuba, Missouri, is yet another outdoor adventurer’s paradise. The area has 20 rustic lodges and campgrounds, three rivers for rafting, and numerous lakes that offer excellent hunting, fishing, canoeing, swimming, and water skiing.
One of the many beautiful murals in Cuba, Missouri, by Kathy Alexander.
Getting its start in 1857, Cuba was founded in anticipation of constructing the southern branch of the Union Pacific Railroad. The town was named in sympathy for the island of Cuba, which was in the news at the time because of Spanish rule. Before the railroad arrived, many people in the area made their living in iron ore mining and farming, with ox carts transporting products to St. Louis. Mining would remain an important industry for nearly 50 years.
When the railroad arrived in 1860, transportation improved, and the town became a shipping center for the region. Soon, apple orchards were planted in abundance. From 1895 through the 1920s, the community was known for its apples and its barrel-making industry. During this time, Cuba became known as the “Land of the Big Red Apple,” and by the turn of the century, Cuba was the largest producer and distributor of apples in Missouri. Apple production declined in the 1930s, but the community still makes barrels.
Wagon Wheel Motel Sign, Cuba, Missouri.
In 1931, Route 66 was completed through the city, and most businesses along the railroad tracks moved closer to the new highway. More new businesses also sprang up along the pavement, including restaurants, filling stations, and motels, answering the needs of traveling motorists. One example is the Wagon Wheel Motel, which still stands at 901 E. Washington. Built in 1934, it was constructed of Ozark native stone and was originally called the Wagon Wheel Cabins. In 1946, it expanded from 9 units to 14. It once also featured a Standard Oil Station and a cafe. Now on the National Register of Historic Places, the retro motel serves weary Route 66 travelers.
At about the same time, higher labor costs drove shoe manufacturers to seek more affordable locations for their plants, and many relocated to rural areas. The shoe industry provided another boon for Cuba and would remain a vital part of its economy for over 60 years.
Restored Carr Phillips 66 Station, Cuba, Missouri.
As you enter Cuba, a “new” stop along Route 66 is Missouri Hick Barbeque. While this place isn’t vintage Route 66, it serves up great Ozark barbecue, and the name itself is so representative of Route 66 that we had to include it. The restaurant, complete with an upstairs outdoor deck, is a great place to watch the traffic during the summer months. It is located at 913 E. Washington Street.
Another vintage peek of the Mother Road is available at the old Carr Phillips 66 Service Station, circa 1932, at Washington and Franklin Streets.
Many small towns along Route 66 display their pride in the Mother Road, but Cuba does it very well with the many murals on its buildings. The Viva Cuba organization completed its first mural in 2001 with plans to complete 12 more. The Missouri House and Senate have proclaimed Cuba as “Route 66 Mural City.”
Just Southwest of Cuba, at 822 Beamer Lane, is Bob’s Gasoline Alley, which displays the most extensive Historic Route 66 gasoline memorabilia collection in the Midwest. This place is a great sight and provides numerous photo opportunities. The buildings are only open during special events, but you can view the outdoor displays at any time.
As you continue your trek along Route 66 to Rosati and St. James, Missouri, you will pass by numerous wineries and vineyards in this rich wine-producing country.
©Kathy Alexander/Legends of America, updated September 2026.
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