PA 239 was designated in 1928 between US 11 in Shickshinny and PA 339 (now PA 487) in Benton. At this time, a portion of PA 393 was designated on the road between Wapwallopen and Mocanaqua while PA 539 was designated between PA 339 in Benton and PA 42 in North Mountain. A section of PA 29 was designated onto the road between PA 93 and Shickshinny in the 1930s, replacing that portion of PA 393. PA 239 was extended to its current length in the 1960s, replacing the portion of PA 29 between PA 93 and Shickshinny and the entire length of PA 539.