The History of Freeport St. Mary High School
Freeport (population 26,443) is located in northwestern Illinois in Stephenson County,
roughly 20 miles south of the Illinois-Wisconsin border, and 25 miles west of Rockford. US Route 20, along with Illinois 26
& 75 connect the city with the rest of the region, as does a line operated by the Canadian National Railroad.
The history of the community is tied to both Indian and immigrant history, originally being called Winneshiek,
before changing its name to Freeport due to a free ferry that was operated by Tutty Baker across the Winnebago River.
Baker was one of the first immigrants from Germany via the state of Pennsylvania that settled in this northern
Illinois town, starting in 1827. When Stephenson County was formed in 1837, Winneshiek became Freeport on 1838 due to the
generosity of Baker, who had also set up a trading post on the river. Freeport grew quickly as it could be reached by stagecoach
in those days from Chicago & had erected a courthouse and school within a few years.
Freeport was also a significant stop during the Lincoln-Douglas Debates in 1858, holding the second of the
seven debates between the two senatorial candidates which would set the stage for the 1860 Presidential campaign that Lincoln
The community is the birthplace of columnist Louella Parsons, basketball star Deacon Davis of Harlem
Globetrotter fame, Black Entertainment Television (BET) founder Robert Johnson, football player Preston Pearson, and television
actress Calista Flockhart.