The City of Carlinville worked tirelessly to create a downtown square any community would be proud to use as a model for development. As with other Illinois communities, coal mining played a significant part of the local economy. This led to Carlinville being the city with the most Sears and Roebuck mail order houses when Standard Oil built 159 of the house for their miners in 1918. 156 of the houses remain today. The city is also famous for the Million Dollar Courthouse and the Cannonball Jail.

Route 66 traveled through Carlinville from 1926-1931 at the height of Prohibition. The infamous Ortic Inn was built on a farm a few miles south of here, and a large barn was rumored to store bootleg liquor. Local tales include secret visits by Al Capone and rum-runners driving the liquor from here to Chicago.