The newspaper was founded in the 1960s by Aubrey C. and Dorothy Wilson as The Cave City Progress.
The newspaper expanded its coverage area in the late 1970s, opening a news bureau in Glasgow and changing the name to The Barren County Progress.
Wilson Jr. also briefly put the Progress on a twice-weekly publication schedule in the 1980s, and also dropped the words "Barren County" from the nameplate for several years in the 1980s and 1990s.
In 2004, the Progress and its sister newspapers were sold by Wilson Jr.—by then the sole remaining member of the Wilson family still involved in the business—to Jobe Publishing, Inc., based in Morgantown and publishers of the Butler County Banner and Green River Republican.
The Times closed on June 9, 2020, leaving The Progress as the only remaining newspaper in Barren County.