Natural Bridge is the site of the second largest Civil War battle in Florida and where the St. Marks River drops into a sinkhole and flows underground for one-quarter of a mile before reemerging.
This site illustrates the crucial role the lay of the land can play in military strategy. In early March of 1865, Union General John Newton and naval Commander William Gibson mounted a two pronged advance toward Tallahassee. Newton landed his troops and headed north, but Gibson's gunboats ran aground in the St. Marks river. When word reached Tallahassee, the limited Confederate forces were quickly reinforced with volunteers. Some volunteers were recuperating veterans, while others were men as old as seventy and boys as young as fourteen.
When General Newton encountered stiff resistance at Newport Bridge, he opted for a surprise attack across a nearby natural bridge. This move had been anticipated by Confederate General William Miller, who entrenched his forces there. The Confederate repelled three Union attacks in twelve hours. Union losses totaled 21 killed, 89 wounded, and 38 captured. Confederate losses totaled 3 killed and 22 wounded.
Deciding the battle was lost, Newton retreated. Southern pride still warms to this victory for it left Tallahassee the only confederate capital east of the Mississippi never to be occupied by Union armies.