[6] When it was incorporated, the new municipality took its name from the generosity of Tutty Baker, who was credited with running a "free port" on the Pecatonica River.

The name "Winneshiek" was later adopted, and is preserved to this day, by the Freeport Community Theatre Group.

On August 27, 1858, the second debate between Abraham Lincoln and Stephen A. Douglas took place in Freeport and gave the nation direction in the following years.

Although Stephen Douglas won the election and retained his U.S. Senate seat, his reply to a question on slavery alienated the South, which called it the "Freeport Heresy", and split the Democratic Party.

Another renowned statue, Lincoln the Debator by Leonard Crunelle, is a focal point in the city's Taylor Park.

The nickname is a reminder of Freeport's ethnic heritage: in the late 1850s, many Germans, both from Pennsylvania and from their European homeland, resettled in Stephenson County bringing with them their love of pretzel snacks.

[10][11] Before February 1893, a large square of land was purchased from the former Keller-Wittbecker farm in East Freeport.

[12] The Arcade Manufacturing Company had been in operation since 1885 when the previous Novelty Iron Works had gone out of business at the corner of Chicago and Jackson streets.

According to the State Climatologist, "the number of days Freeport has experienced heavy rainfall has steadily increased every decade since 1949.

One study estimates that for "every $1 communities like Freeport spend to relocate their residents they will save $6 in future clean ups.

33.7% of all households were made up of individuals, and 15.1% had someone living alone who was 65 years of age or older.

Tourist sites in the area include the Don Opel Arboretum, a botanical garden with over 3,000 different species of ground coverings, trees and shrubs.

[23] Local Freeport media includes WFRL (1570 AM), WFPS Radio (92.1 FM) and The Journal Standard daily newspaper.

Freeport and surrounding Stephenson County is serviced by Pretzel City Area Transit (PCAT) This is a private company in a partnership with the Senior Resource Center, the city of Freeport provides small bus and/or van transportation throughout all of Stephenson County.

Freeport has a rail line running east and west on the north side of city.