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Freeport is the county seat and largest city of Stephenson County in northwestern Illinois, sitting along the Pecatonica River about 20 miles south of the Wisconsin state line and 114 miles northwest of Chicago.

Freeport was originally called Winneshiek, and it took its present name from the generosity of Tutty Baker, who was credited with running a "free port" on the Pecatonica River.

Freeport became the seat of Stephenson County in 1838, a frame courthouse went up in 1840, and its first school was founded the same year.

On August 27, 1858, Freeport hosted the second of the seven Lincoln-Douglas debates, where Stephen A. Douglas's answer to Lincoln's question became known as the "Freeport Doctrine" and helped split the Democratic Party before the 1860 election.

Freeport's debate site is preserved at Debate Square in the downtown, and a debate monument at the site was dedicated by President Theodore Roosevelt in 1903.

Freeport is nicknamed "Pretzel City, USA" because German immigrant John Billerbeck's bakery, founded in 1869, distributed so many pretzels that the local newspaper dubbed it the Pretzel City; Freeport High School's teams are still called the Pretzels.

Freeport started its first Pretzel Festival in 2003, and at Pretzel Fest in 2025 more than 600 people formed the world's largest human pretzel formation, beating a record of 529 set in France in 2019.

Freeport had a population of 23,973 at the 2020 census, with 10,528 households and a median age of 43.7 years.

Freeport is home to Highland Community College, established in 1962, whose first 229 students took evening classes at Freeport Senior High School; the college's foundation was the first community college foundation in Illinois and only the second in the nation.

Freeport has the oldest Carnegie Library in Illinois, a building designed by the Chicago firm Patton and Miller that was renovated and became Carnegie City Hall in February 2017.