The railroad was conceived and financed by leading cotton planters who needed a way to get their crop to textile mills in England and New England. It was also used by naval store merchants and timber interests of the area to transport the their goods to East Coast ports.
The Tallahassee Railroad Company was approved in 1835 by the Florida Legislative Council. Also that year, the Tallahassee Railroad Company received the first Federal land grant to a railroad. In 1835 construction began on the Tallahassee St. Marks Railroad.
The drawing by Francis Count de Castelnau is captioned with: "Railway depot at Tallahassee. Florida already has a railroad, which although short renders great service. It extends from the capital to Saint-Marck on the Gulf of Mexico about 7 leagues away. It crosses such a very deep sandy region that, before construction, it was scarcely possible to cross it on horseback. It serves chiefly to transport cotton from the interior to the sea."
The railroad was completed in 1837 and began operation that year. It was a mule-drawn railroad that connected Tallahassee, Florida, then the territorial Capital, with the Gulf port of St. Marks — a distance of 22 miles (35 kilometres). By 1838 the railroad extended three miles south to Port Leon.
In 1843, Port Leon destroyed by massive hurricane. The railroad terminal there is moved back to St. Marks. In 1856, the wooden rails are replaced by steel rails and mules are replaced by locomotives. During the Civil War, the Confederates used the railroad extensively to move troops, artillery and supplies in defense of Tallahassee. In March 1865, the railroad achieved its highest military significance when it was used to deploy Confederate troops quickly south from Tallahassee in the face of an advance by Union troops. The railroad enabled Generals Samuel Jones and William Miller to put enough men into place to defeat Union General John Newton at the Battle of Natural Bridge on March 6, 1865. In 1880, the railroad began to transport naval stores and timber for Leon County's logging industry.
In 1983, the Seaboard Railroad filed to abandon the line between Capital Circle in Tallahassee and St. Marks. The Tallahassee-St. Marks line has the distinction of being the longest operating railroad in Florida and served the area for 147 years. One unknown traveler called it "the worst that has yet been built in the entire world." In 1984 the corridor was purchased by the Florida Department of Transportation. The Florida Park Service currently maintains it as the St. Marks Trail.
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