Looking to shorten the travel time between Savannah and Jacksonville, railroad entrepreneur Henry B. Plant had this 70-mile line constructed in 1880-81. Beginning at Waycross, which was the closest point on his Savannah, Florida & Western Railway to Jacksonville, the 33-mile Waycross & Florida Railroad was built southeastward to the state line. There it joined the 37-mile East Florida Railway, built at the same time, which continued the route to Jacksonville. The two railroads were operated together under the marketing name Waycross Short Line.
The new line cut travel time between Savannah and Jacksonville in half as it bypassed the previous route through DuPont, Georgia, and Live Oak, Florida.
Today the line forms the western section of CSX's Folkston Funnel where up to sixty trains per day pass through the railroad's two lines converging at Folkston.