[8] It had busy early years due to heavy river traffic and its position as an entry point into the Indiana Territory along the historic Old Michigan Road.

Conrail much later bought Pennsylvania Railroad, but the deal left out a 26-mile (42 km) stretch of track from North Vernon to Madison.

During the late nineteenth century, many new buildings were still being built, but in many cases older structures were modernized by adding cast-iron storefronts and ornamental sheet metal cornices.

Downtown Madison was granted National Historic Landmark District status in early 2006.

Authorities stated that the cause of the fire was a contractor using an open-flame propane torch to solder two pieces of copper together in one of the built-in gutters on the north side of the roof.

From April 3 to April 4, 1974, there were 148 tornadoes confirmed in 13 states, including Illinois, Indiana, Michigan, Ohio, Kentucky, Tennessee, Alabama, Mississippi, Georgia, North Carolina, Virginia, West Virginia, and New York; and the Canadian province of Ontario.

[16] The 1974 Super Outbreak remains the most outstanding severe convective weather episode of record in the continental United States.

Shortly after an F-5 tornado struck Depauw, northwest of Louisville, the Hanover/Madison F4 twister formed near Henryville and traveled through Jefferson County, leveling many structures in the town of Hanover and in Madison.

Indiana State Road 7 has its southern terminus in Madison and leads northwest 23 miles (37 km) to Vernon.

[18] The climate in this area is characterized by hot, humid summers and generally mild to cool winters.

In 1929, the city began holding an annual race, later called the Madison Regatta beginning in 1948.

Since 1954, the Madison Regatta has held a high points Unlimited hydroplane race annually in early July.

The boat, which has been known by various corporate sponsor names but was officially called U-6, traditionally finished near the bottom of the circuit.

The Gold Cup winner retired at the end of the year, taking second place in the overall national standings, and was replaced with a new Miss Madison in 1972.

The Miss Madison's greatest accomplishment, when it seemingly came from out of nowhere to win the 1971 Gold Cup with an aged boat against powerful competitors such as Atlas Van Lines II and Miss Budweiser, was recreated in the semi-fictional film Madison.

Oberto driver Steve David announced his retirement after his final run at the San Diego Sea Fair.

The Madison-based team continues to compete in the H1 Unlimited championship, with driver Jimmy Shane and sponsor HomeStreet Bank, who have been with the squad since 2016.

In the summer of 1957 Madison was selected as the location for Some Came Running, which brought actors Frank Sinatra, Dean Martin and Shirley MacLaine to town.

For Some Came Running, released in 1958, director Vincente Minnelli selected Madison to represent the fictional town of Parkman in filming the James Jones novel.

The filming brought notable stars such as Jim Caviezel, Bruce Dern, Paul Dooley, and Mary McCormack to town.

Madison was released in 2001 and recounts the story of the city's hosting and winning the penultimate hydroplane racing event of 1971, echoing the movie Hoosiers.

A Netflix Docuseries titled Girls Incarcerated was filmed there about the former Madison Juvenile Correction Facility.