Madison’s downtown historic district contains over 1,520 nineteenth century structures (133 blocks listed on the National Register of Historic Places) designating it Indiana’s largest historic district.
Madison's historic downtown was designated a National Historic Landmark Distrist in 2006.
Madison is one of twelve Distinctive Destinations of 2001 selected by the National Register of Historic Preservation.
Jefferson County has 3 National Historic Landmarks: Lanier Mansion State Historic Site, Shrewsbury-Windle House, and Eleutherian College.
Eleutherian College, founded in 1848, was the 2nd Indiana educational institution to admit students without regard to race or gender, and the 1st to offer college classes to African-Americans.
Hanover College, founded in 1827, is the oldest private college in Indiana.
Schroeder Saddletree Factory is the last remaining 19th century saddletree factory in the nation.
The Masonic Schofield House is the site of the organizing of the Grand Lodge of Free Masons of Indiana on January 13, 1818.
Fair Play Fire Company #1, located in downtown Madison, is the oldest volunteer fire company in the state. It was established on September 15, 1841.
Chelsea Jubilee is the oldest festival in Indiana and began in 1866.
Irene Dunn, noted movie actress, spent her entire childhood in a house located on 916 W. Second Street. Following her graduation from Madison High School, she went to Chicago, her first step on her road to fame. She was born in Louisville, Kentucky.

Frank Bellamy, author of the Pledge of Allegiance, was born in Madison on September 15, 1875.While attending high school his class was asked to write their ideas of their debt to their country and their duty to its government. Bellamy’s article so impressed a visitor to the school, that she preserved it and later when the fervor of patriotism was thriving during the war with Spain, it was selected as the pledge of allegiance for our country.
Madison was the site of the filming of the Hollywood motion picture "Some Came Running" starring Frank Sinatra, Dean Martin, and Shirley McClain.
Madison was the site of the filming of "Madison" the movie. It is the story of the 1971 Indiana Governor's Gold Cup Hydroplane Race won by Miss Madison. The movie has been previewed at Sundance Film Festival and Heartland Film Festival and is scheduled for release early in 2002.
Dr. Harvey W. Wiley, born in Kent, was the father of the Pure Food and Drug Act.
Gail Borden, a childhood resident of Jefferson County, was the inventor of condensed milk, which revolutionized the dairy market.
Tommy Thevenow, a Madison native, was the star short stop of the 1926 World Series Champions – the St. Louis Cardinals.
Madison was one of the first three pilot Main Street Programs in the country selected by the National Trust for Historic Preservation.

Madison was established in 1809, which predates Indiana statehood by 7 years.
During the 19th century, Madison was one of the largest Pork Packing points in the world, earning it the "Porkopolis".
Madison has the steepest grade non-cog railroad in the United States (5.89%).Irish immigrant railroad workers used the stones from the incline to construct St. Michael the Archangel Catholic Church in 1839.
Madison has the only City owned unlimited hydroplane racing boat in the world: Miss Madison.
Madison-Jefferson County library was the first public library in the Northwest Territory.
Notable visitors to Madison include: President Andrew Jackson in 1829, President Polk in 1835, Herbert Hoover in 1929, Charles Lindbergh in 1956, Robert Kennedy and Guy Lombardo.
Jenny Lind (the Swedish Nightingale) performed in Madison in 1851. Madison was the smallest city in which she performed on her American tour. Ms. Lind sang in the largest building in Madison, which was a pork house.