Home to a number of plantations, Gloster became a functioning place only after the Texas & Pacific trains came through (and an engineer lent his name to the whistle stop). Speaking of transportation, Gloster was home to Louisiana Tolbert Dowling, a state senator and also the president for the Jefferson Highway ("From Palm to Pine!") in 1919. Dowling, an early proponent of the Good Roads movement, made sure that Gloster was a stop on the Jefferson Highway. Today, though, US 171, which approximates the Jefferson Highway alignment, is almost two miles west of Gloster's Main Street.
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