Leslie was incorporated in 1892. The town was given its name from a Victorian lady named Leslie Bailey. Today, the town still looks much the same as when she strolled the dogwood-lined streets and well-kept white houses more than a century ago. A large part of Leslie belongs to the agribusiness sector of Sumter County. Rolling farmland and rumbling tractors harvesting produce throughout the year is the common sight driving through this part of Sumter County.
Leslie is home to the Antique Dogwood Festival each year in April. The festival, held in the town's civic center, brings antique dealers from across the state. A variety of antique merchandise from coin collections to furniture can be purchased at this annual festival.