Darlington's Main Street is the heart of the City with six picturesque blocks of businesses, churches, museums, government offices, and more. Darlington's Main Street is on the National Register of Historic Places and it's no wonder why when one pauses to gaze upon the beauty of its historic architecture. It was listed as a historic district on the National Register of Historic Places in 1994. It included 40 contributing buildings on 8 hectares (20 acres).

It includes Darlington's old downtown:

The 1860 J.B. Cutting Livery Stable; 130 E Ann St.

The 1879 Italianate-styled Schreiter Building; currently Legends Pub & Grill.

The 1883 Romanesque Revival Driver's Store and Opera House; still known as the Driver Opera House.

The 1896 Queen Anne Miller and Fardy Dry Goods Store; currently LillyGene Collective.

The 1911 Neoclassical Odd Fellows Hall; currently Iglesia Apostolica de la fe en Cristo.

The 1919 Clayton's New & Used Furniture; currently Main Furniture & Home.

The 1930 Moderne-style Iowa Oil Co. & Filling Station; currently City Service Brewing.

The First National Bank building was probably designed by an architect. But the Citizens National Bank (1885), at 330 Main Street, is the only building known specifically to have been architect-designed: its new facade in 1928 was designed by Madison, Wisconsin architects Frank Riley and Lewis Siberz. According to the NRHP nomination, the building's facade has monumental fluted Doric pilasters, an entablature, and a pediment "enriched with a large medallion", and overall "recalls a Greek temple front."

Even Director Michael Mann realized the beauty of Darlington's Main Street and took advantage of its historic structures when creating the movie, Public Enemies. Universal Studios filmed portions of the movie, which starred superstar Johnny Depp, in the Lafayette County Courthouse on Main Street.

Whether you're looking to start a new business or just visit, Darlington's Main Street is definitely the place to begin.