The Pennant was established in 1946 and services Penola and surrounds including the famous Coonawarra Wine Region.

The Pennant was founded by W. Erwin Thiele, who felt that a publication to service the town and local areas was needed after a "lack of communication from Mount Gambier and Naracoorte was evident".

Kenneth Victor Dohnt (a New Zealander), purchased the paper in 1950 and maintained it until his death in 1971. It was then controlled by Lyle Shurdington, a local and long-time employee, and in October 1978, it was taken over by South East Telecasters, whose major shareholder was Allan Scott, of the Scott Group of Companies.

The newspaper ceased publication for 18 months in 2020-2022 due to financial difficulties but was successfully relaunched in 2022 after being purchased by TBW Today Pty Ltd, a company owned by a group of experienced publishers.