'Pretzel City' Is A Delightfully Quirky Illinois City With Culinary Treats And Midwest History

Although a small town in Pennsylvania is home to the oldest pretzel bakery in America, there's a city in Illinois that claims the title of "Pretzel City" because of an infamous bakery in the town started by a German immigrant baker around 1860. On Illinois State Route 20, if you're making your way from the city of Rockford west to the cozy, historic Midwest town of Galena, you'll pass the city of Freeport, Illinois, located on the Pecatonica River. Situated in Stephenson County just one hour east of Galena and an hour south of Monroe, Wisconsin, the city of Freeport may seem like a quaint town on the way to somewhere else. But this small city offers plenty of American history and notable spots worth stopping to experience, including outdoor parks, nature trails, restaurants, museums, festivals, and — well — pretzels.

According to the Freeport Journal-Standard, the small city's oldest newspaper, "It is believed the Billerbeck Bakery instituted the production of pretzels, which became the trademark for the city and the athletic teams of Freeport High School." Freeport doesn't take its nickname lightly: the Pretzel City puts on an annual Pretzel Fest complete with live music performances, polka dancing, games, and pretzel-themed souvenirs. In 2025, the festival attempted to create a world record by photographing the largest pretzel shape created by humans. If you're traveling to Freeport during football season, attending a local high school Pretzels Game is a must. Check out the Freeport High School website for their annual calendar. To get to Freeport, you can fly into the Chicago Rockford International Airport, about 30 minutes away, or into Chicago O'Hare International Airport, about an hour and a half drive away.

Originally called Winneshiek after a Native American chief before the town was officially incorporated in 1838, the land now known as Freeport was once inhabited by the Winnebago tribe of Native Americans who farmed the river region's fertile soil. European settlers arrived in the early 19th century, and Freeport became a major stop along the Stagecoach Trail. In 1858, Freeport hosted the second Lincoln-Douglas presidential debate, a landmark historical event where Abraham Lincoln and Stephen Douglas vied for a seat in the Illinois state senate. In fact, a notable speech Douglas gave about states' rights became known as "the Freeport Doctrine" which ultimately helped Lincoln win the presidency two years later. Travelers can visit a monument of the debate at the Lincoln-Douglas Debate Square behind the Freeport Library. After visiting Debate Square, visitors recommend tasting the ice cream at Union Dairy, just around the corner. Staying in theme, The Great Debate Bar & Restaurant serves cocktails and fine dining with Midwest flair with dishes like prime rib, beef stroganoff, and cinnamon roll pork belly bites. 

To experience Freeport like a true local, you must try Mrs. Mike's for rich, caramel popcorn. For an alternative Freeport vibe, visit Duckman's Jerk Shack for Caribbean-style food and some of the richest flavors in town. After the Friday night lights dim on Pretzel Field you can often see the football team in their high-school letterman jackets eating post-game pizza at Cannova's Italian Cuisine. Since 1921, Cannova's has served up pasta, pizza, and live piano music on weekends. No stop in Pretzel City is complete without Stephenson Street Pretzels & Italian Ice for big, soft pretzels and slushy-style drinks. And no self-respecting Midwest city would be caught without a craft brewery. In Freeport, Generations Brewing Co. has regular and rotating taps.

One of Freeport's biggest parks is Read Park, which not only offers shuffleboard courts, a skate park, and an aquatic center but also a miniature replica of Chicago's famous Wrigley Field where you can play catch and run the bases. Down the road, Oakdale Nature Preserve is a large reserve of restored natural landscapes with several miles of trails and a historic, steel tabernacle that has been a longtime restoration project and is closed as of this writing. The 74-acre Taylor Park has a statue of Abraham Lincoln as well as basketball courts and picnic areas. Krape Park is a favorite because of its carousel, swan paddle boats, amphitheater, disc golf courses, tennis courts, cross-country trails, vast forested areas, and 44-foot waterfall. There are a number of walking trails, too. The Jane Addams Recreation Trail is a major attraction for cyclists and those pushing strollers. Named for the early-1900s activist born nearby, the fairly flat, 17-mile trail runs through Stephenson County up to Wisconsin with several trailheads in Freeport.

The Freeport Art Museum has suggested-donation admission and features exhibits ranging from 19th-century Bolivian textiles to rotating art collections. The Silver Creek Museum displays engines and machinery and lets visitors ride an operational 1912 steam locomotive (now running on diesel fuel). The Stephenson County Historical Society Museum and Arboretum is a great place to learn about the history and natural history of this unassuming Midwestern region. If museums aren't your thing, the Winneshiek Players performs a variety of work in a historic, local theater. So, as you can see, although Freeport isn't on America's most underrated Midwest road trip route, it's certainly worthy of a stop even if you're just passing through.