Freeport, IL

In 1827, German settlers from Pennsylvania began arriving in the Freeport area to make their homes. Among them was William “Tutty” Baker, credited as the founder of Freeport, who built a trading post on the banks of the Pecatonica River. A generous man, Tutty Baker began operating a free ferry across the river and even invited travelers into his home for meals and lodging.

Originally called Winneshiek, the community took its name from the fact of Baker’s renowned generosity – “Free Port” – when it incorporated. Winneshiek was later adopted and is preserved to this day by the Freeport Community Theatre Group.

In 1837, Stephenson County was formed and in 1838, Freeport became its seat of government. Linked by stagecoach with Chicago, the community grew rapidly. In 1840, a frame courthouse was erected and the first school was founded. Within two years, Freeport had two newspapers and in 1853, the two were joined by a third which published in German. By then, the community had a population of 2,000.

On August 27, 1858, the most significant of the historic Lincoln-Douglas debates took place in Freeport and gave the nation direction in succeeding years. Although Douglas won the election and retained his senate seat, his reply to a question on slavery alienated the South, which called it the “Freeport Heresy,” and split the Democratic Party. This enabled Lincoln to win the Presidency in 1860.

A monument to the debate was dedicated in 1903 by President Theodore Roosevelt and stands at this site. A life size statute recreating the event was dedicated in 1992. Another renowned statue, “Lincoln the Debater.” by Leonard Crunelle, is a focal point in the city’s Taylor Park.

The Stephenson County Historical Society preserves local history in “Bohemiana,” an Italiante mansion once owned by Oscar and Malvina Taylor and listed in the National Register of Historic Places. The Taylor’s devoted their energies to creating an arboretum at the site and today it contains the largest variety of old trees in the county. Also on the property there is a Farm Museum, a relocated one-room schoolhouse, and an 1840 log cabin.

The Taylor’s hosted many guests at Bohemiana, including such well known personalities as Horace Mann, Horace Greeley, Stephenson County native Jane Addams, Edward Everett Hale, and Ralph Waldo Emerson.

Freeport is the birthplace of several celebrities. Among them is Calista Flockhart, the star of the Fox Network’s acclaimed “Ally McBeal” television show. Other noteworthy personalities born in Freeport include Louella Parsons, the famous columnist; Deacon Davis of Harlem Globetrotters fame; Robert Johnson, founder of BET, and Preston Pearson, NFL football star.

Freeport offers its citizens a very diverse lifestyle, incorporating the best of the old and new, the large and small. Tree-lined boulevards boast gracious 100+ year-old homes while new subdivisions offer the latest in design and construction. Our citizens are a diverse lot, providing a cultural mix sometimes lacking in mid-size communities. And our location– in the middle of a rural America yet close to several of the Midwest’s most progressive big cities–provides our residents with a myriad of choices to enhance their professional and personal lives.

Sponsors of Freeport, IL


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Businesses of Freeport, IL


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Stephenson County, IL


Visit our county page and you will learn about the contributions made by the citizens from our town and county (founders, business people, volunteers, entrepreneurs and military veterans). Here you will find information about our town and county's points of interest, festivals/events and faith community. You also will learn about the community organizations that have built and continue to build strong communities (chambers, community groups, and departments, etc) and much more when you visit the Stephenson County, IL page.