In October 1864, a small Union force of 55 men of the 4th Massachusetts Cavalry conducted a raid on Middleburg from their strongpoint at Magnolia near Green Cove Springs. The raiders

burned warehouses and other buildings, and looted the remaining houses and businesses.

Captain J.J. Dickison, commander of Confederate forces in the area, was notified of the raid and rushed to intercept them on their return to Magnolia. Near Halsey's Plantation, the Confederate force engaged the Union raiding party and routed them with heavy casualties in a skirmish known as the Battle of Big Gum Creek.

The Union forces reported losses of 29 killed, wounded and captured, while the Confederate report claimed slightly higher Union casualties of 33 to 35. The Confederate report stated that they had suffered no casualties but only lost several horses.

Information Provided by the Florida Department of State.