The paper began as the weekly Windsor Record in 1888, changing its name to the Border Cities Star in 1918 when it was bought by W. F. Herman. It became the Windsor Daily Star in 1935 following the amalgamation of several small communities, and finally the Windsor Star in 1959. Although Herman died in 1938, the paper continued under the direction of his wife, Adie Knox Herman, along with Hugh Graybiel and W. L. (Lum) Clark.
The paper was sold to Southam Press in 1971, and then to Canwest (who bought Southam Press) in 2000.
In November 1996, the paper opened a printing facility in south-central Windsor.
1927 Windsor Star Building at 167 Ferry Street