The History of Madison County

The First Peoples and Hernando de Soto

The only recorded archaeological site inside Madison Blue Spring State Park is a thin scatter of stone flakes and finished tools. State site records list it as Archaic, and possibly Paleoindian. The tools now lie under the spring run and the Withlacoochee River, but that ground was likely dry during the Pleistocene. Florida State Parks says local people once used the spring for fresh water. The park has never had a full archaeological survey.

In 1539, Hernando de Soto and 700 soldiers landed at Tampa Bay and later passed through the Suwannee Valley. According to a local history, he had a bridge built over the Suwannee River and crossed into what is now southern Madison County. His army reached the Aucilla River two days after that and was attacked there, one of several attacks by Native people on the march.

Sources: Florida Department of Environmental Protection: Madison Blue Spring State Park, park chapter of the unit management plan; Florida State Parks: Madison Blue Spring State Park, History; Greene Publishing: De Soto Sought Wealth in Madison County (December 10, 2020)

Madison County Is Created in 1827

Madison County was created by the Legislative Council on December 26, 1827. The county took its name from James Madison, who was the fourth U.S. president. Mrs. Elizabeth Carter's home at San Pedro is the first recorded building to serve as the county's courthouse. A log courthouse went up nearby soon after. The county's first marriage license was issued on January 25, 1831.

Dennis Hankins is the earliest clerk of the county court on record. In May 1831, Hankins and Silas Coker each hosted voters at home for the election of the territorial delegate to Congress. The first Superior Court in the county was organized at the San Pedro courthouse on June 6, 1835. San Pedro stayed the county seat until 1838.

Sources: Florida Memory, State Library and Archives of Florida: WPA Madison County (county history typescript); Greene Publishing: History of the Madison County Courthouse (April 29, 2021)

Cotton, Slavery, Factories and the First Train

William Bailey, the region's largest enslaver, built up The Cedars, a 4,000-acre cotton plantation on land that later became part of Livingston Place. In 1850, The Cedars held some 269 enslaved African Americans who were forced to work its land. Their forced labor produced 8,000 bushels of corn and 550 bales of cotton that year.

In 1851, Roswell H. Willard opened Stillapika, a shoe factory some ten miles south of the town of Madison. A WPA county history calls it the first business of its kind in Florida. The Tallahassee Floridian reported on December 3, 1853, that 26 enslaved workers there made 11,000 pairs of shoes a year. Also in 1851, Captain N. P. Willard built a $30,000 cotton factory in Madison, which burned in 1857.

The St. Johns Seminary of Learning was started in 1850 by Madison Lodge Number 11, F.& A.M. Two new counties, Taylor and Lafayette, were cut from Madison County in 1856. Work on the Georgia and Pensacola Railroad through the county started in 1859, on a route that crossed the Aucilla River, ran through Sandy Ford, now Greenville, and passed just south of Madison. Madison held a celebration for the first train on July 4, 1860.

Sources: Florida Department of State, Florida Historical Markers: The Cedars; Florida Memory, State Library and Archives of Florida: WPA Madison County (county history typescript); Florida Department of State, Florida Historical Markers: St. Johns Seminary of Learning; Greene Publishing: Madison County's First Train (September 10, 2021)

Governor Drew's Ellaville and the Growth of Greenville

In the mid-1860s, George F. Drew set up a sawmill and manufacturing center at Ellaville, near where the Withlacoochee River meets the Suwannee. His two-story mansion nearby, built in the late 1860s, had color-matched oak parquet floors and formal gardens, and it stood until fire destroyed it in 1970. Drew served as governor of Florida from 1877 to 1881, just after Reconstruction. Ellaville thrived as long as the yellow pine lasted, then declined after 1900, and the town was gone once its post office shut in 1942. A flywheel from the Ellaville sawmill is on display at nearby Suwannee River State Park.

Greenville began in 1850 as a place called Sandy Ford, and Samuel Williams became its first postmaster in 1854. The railroad knew it as Station 5, and in the 1860s it took the name Greenville, after Greenville, South Carolina. Elijah Hays helped the town grow after 1876. He bought much of the land the town sits on and ran farms, stores, a cotton gin and a turpentine still.

The town of Madison's first courthouse burned in March 1876, on March 23 according to the local paper and on March 26 according to the WPA history. Work on a new brick courthouse began in March 1880.

Sources: Florida Department of State, Florida Historical Markers: Drew Mansion Site / The Town of Ellaville; Greene Publishing: The Town of Ellaville (July 7, 2016); Florida Department of State, Florida Historical Markers: The Town of Greenville; Greene Publishing: Just Who Was Haffye Hays? (March 26, 2020); Greene Publishing: History of the Madison County Courthouse (April 29, 2021); Florida Memory, State Library and Archives of Florida: WPA Madison County (county history typescript)

Quail Plantations, Cherry Lake Farms and Young Ray Charles

In 1926, a group of New York investors that included Gerald M. Livingston purchased the old Cedars land, and Livingston later bought out his partners. From 1926 to 1994, the Livingstons of New York used it as a winter estate they called Dixie Plantation, which grew to more than 18,000 acres across the Florida-Georgia line. In 1936, the architect John Russell Pope, known for the Jefferson Memorial, designed a three-story brick mansion there overlooking Lake Windom. At the peak in 1940, in the years of Jim Crow, 400 Black workers lived there with their families in a community of their own.

In the early 1930s, the federal relief agency FERA bought 15,000 acres at Cherry Lake for a New Deal farm settlement. More than a hundred families had come there from Tampa, Jacksonville, Miami and other cities by 1935. They lived in 170 cottages with phones, water and electricity. Around 1937, a 12-acre piece of land on the lake's west shore was leased for a camp, and the site later became a 4-H camp.

Ray Charles was born in 1930, and until he was about five he lived in a small Greenville house with his mother, Aretha Williams, and his adopted grandmother, Margaret Robinson. The house had no indoor plumbing and no electricity. He got his first piano lessons from Wiley Pitman, who owned the nearby Red Wing Cafe. His sight failed at age seven, and he then left for the Florida School for the Deaf and Blind in St. Augustine.

Sources: Florida Department of State, Florida Historical Markers: The Cedars; Florida Department of State, Florida Historical Markers: Livingston Place; Greene Publishing: History of Cherry Lake (April 7, 2016); Greene Publishing: Madison County in the Thirties (June 28, 2018); Florida Department of State, Florida Historical Markers: Ray Charles Childhood Home; WTXL ABC 27: Artist paints interactive piano mural to honor Ray Charles' North Florida roots (June 24, 2026)

Since 1990: Ray Charles Remembered, a Museum and a Spring Park

In 1998, Judge Charles McClure of Tallahassee donated the W.T. Davis Building, and it was restored as the home of the Treasures of Madison County Museum. The building joined the National Register of Historic Places in 2015, and a state marker was put up there on June 3, 2016. On October 26, 2002, the state bought the land at Madison Blue Spring, a first-magnitude spring on the Withlacoochee River's west bank. A six-mile rail trail between Hanson and the Withlacoochee River, on the old Valdosta Southern line, was finished in 2007. Called the Four Freedoms Trail, it now reaches from Madison north to the Georgia line at the Withlacoochee River.

In 2006, Greenville bought the run-down house where Ray Charles had lived as a boy, which was slated to be torn down. That same year, a bronze statue of Charles was put up in the town's Haffye Hays Park, two years after his death. With a grant from the Florida Bureau of Historic Preservation, the town finished rebuilding the Ray Charles Childhood Home in 2008. In 2025, the Hot Tamales Band played a tribute concert in the park to mark the 95th birthday he would have had. On July 18, 2026, Greenville unveiled a new piano mural honoring Ray Charles, painted by Quincy artist Devonte King.

In 2013, the Livingston family's foundation gave Livingston Place to Tall Timbers, a research and land conservation group, which restored the main house in 2021. In 2016, the college in Madison celebrated the 50th anniversary of its merger with Suwannee River Junior College.

Sources: Greene Publishing: Historical Marker Established for W.T. Davis Building (June 9, 2016); Florida Department of State, Florida Historical Markers: W.T. Davis Building; Florida Department of Environmental Protection: Madison Blue Spring State Park, park chapter of the unit management plan; WTXL ABC 27: Road Trip story on the Madison County rail trail (July 16, 2015); TrailLink: Four Freedoms Trail; Florida Department of State, Florida Historical Markers: Ray Charles Childhood Home; WTXL ABC 27: Artist paints interactive piano mural to honor Ray Charles' North Florida roots (June 24, 2026); WCTV: Greenville celebrates Ray Charles' 95th birthday and lasting impact (September 24, 2025); Greene Publishing: Just Who Was Haffye Hays? (March 26, 2020); Greene Publishing: Ray Charles Memorialized with Piano (July 21, 2026); Florida Department of State, Florida Historical Markers: Livingston Place; North Florida College: Suwannee River Junior College