The first hard road connecting Chicago and St. Louis passed through the heart of Carlinville. In 1926, Route 66 opened from Chicago to Los Angeles and followed Route 4 through Illinois. The “Mother Road” circled the Carlinville Square until 1930, when it was rerouted and bypassed Carlinville to the east. The Ariston Restaurant opened on the Carlinville Square in 1924, and business boomed when Route 66 was routed through town. When the highway moved to Litchfield in 1929, the Ariston’s owner decided to follow, and the restaurant remains open there today serving Historic 66 travelers. From 1838 to 1869, the Macoupin County courthouse stood on the public square, where Abraham Lincoln represented clients as a circuit court rider. In 1869, the famous “million dollar courthouse” was built off the square and is still in use today. In 1913, Carlinville was transitioning from horse and buggy travel to the automobile, and the Loomis House, a 50 room hotel and local landmark, stood by the square. In the late 1940s, the square was seen with a view of the courthouse.