The Middleburg Historic District contains five historic buildings: The Federal Road (also referred to as "Military Road") was constructed between 1824 -- 1827, and provided access to Fort Heileman during the Second Seminole War, spanning Colerain, Georgia to Tampa, while traversing the villages of Garey's Ferry and Whitesville, as well as providing military infrastructure and increasing development and settlement in the area.

On October 23, 1864, during the American Civil War, the 4th Massachusetts Volunteer Cavalry engaged local Confederates in a skirmish from their base at the Magnolia Springs hotel.

The 2nd Florida Cavalry, under command of Captain J.J. Dickison, retaliated by firing on the Massachusetts regiment, leading the latter to retreat across Black Creek and burn the ferry bridge behind them.

[6] Before Middleburg was consolidated into its current town limits, the area comprised two distinct settlements upon each prong of Black Creek, within miles of each other.

The site of Middleburg's historic black community, Hill Top was first settled by homesteaders, including Grant Forman (1868-1951), in the 1890s.