The community of Chaires was established in the 1820s during Florida's Territorial Period from 1821 to 1845. It was named for Green Hill Chaires, who came from Georgia with his brothers Benjamin and Thomas Peter and established vast plantations in eastern Leon County. Chaires plantation eventually grew to 20,000 acres with a home on Lake Lafayette, but that home was later destroyed, and in 1839 during the Second Seminole Indian War, his wife, two of his children, and several of his slaves were massacred. He then built a house called Evergreen, and his brother Thomas Peter built a house called Woodlawn. In 1851, Green Chaires built the state's first plank road, connecting upland plantations to the Gulf Coast shipping communities of Newport and St. Marks. The establishment of Railroad Station #1 in 1857 and the Chaires Post Office in 1858 strengthened the sense of community. By the turn of the century, Chaires had become the commercial hub for the area, with a cotton gin and packinghouse, public schools, stores, and churches, and it retains much of its turn-of-the-century character today.