Madison, Florida

Madison, Florida is the city where the 1950s never ended! Located on US 90 west of Wlive Oak, Madison (population 2,912 in 2020) features the preserved atmosphere and culture of the 1940’s and 1950’s with vibrant downtown shopping in buildings with antebellum architecture. The city’s Episcopal church is still active in its 1843 original building. Old Main Street hosts Grmpy’s Diner and Pie Shop and numerous boutiques with traditional Deep South apparel and contemporary fashions and there is an antique store with clothing and childrens’ toys of the 1920s-1950s.Historically, Madison gained national attention as the hometown of the nation’s first World War 2 hero, Captain Colin P. Kelly. On December 10, 1941, three days after the Pearl Harbor attack, Kelly’s B17 Flying Fortress crew successfully bombed the Japanese cruiser Ashigara, but Japanese Zero fighter aircraft disabled Kelly’s aircraft as it attempted to return to Clark Field in the Philippines. Kelly ordered his men to parachute to safety but he was killed when the bomber crashed before reaching Clark Field. President Franklin Roosevelt commissioned the building of the Four Freedoms Monument in Kelly’s memory which is the dominant statue in Four Freedoms Park. Captain Kelly is buried in the city cemetery along with Florida Governor Cary A Hardee (1921-25) and 23 unidentified Confederate dead killed in the Battle of Ocean Pond/ Olustee.

Madison also is the home to O’Neal’s Country Buffet, a multi-county destination restaurant, and the North Florida Community College, long considered as “The Friendliest Small College in Florida.”