The Trace follows a timber railroad. The Pearl & Leaf Rivers Railroad was incorporated on November 20, 1897, as a division of the J. J. Newman Lumber Company, to build west from the company's sawmill at Hattiesburg. By 1901 the line reached Sumrall, 19 miles out, where Newman opened more mills. The route later became part of the Mississippi Central Railroad, which grew to more than 150 miles and was sold to the Illinois Central in the late 1960s. When the railroad cut its system back, the tracks between Hattiesburg and Prentiss came up in the early 1990s.
Local people kept the right-of-way together, and the Longleaf Trace was completed in 2000 as a Rails-to-Trails project. It runs 44 miles on asphalt from a gateway near the University of Southern Mississippi to Prentiss, through five communities in Forrest, Lamar and Jefferson Davis counties. The three counties and four towns jointly run it as the Pearl & Leaf Rivers Rails-to-Trails Recreational District, paid for in part by a small property tax levy. Walkers, cyclists and riders on horseback share it.
The Piney Woods it crosses were ceded by the Choctaw in 1805 and were then a belt of virgin longleaf pine. The Trace takes its name from that tree. One National Register account of Hattiesburg's timber boom says the race to cut the forest took less than forty years, and the railroad is what carried it out.
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