Discover the Unexpected in Stephenson County Discover the Unexpected in Stephenson County

Discover the Unexpected in Stephenson County

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Stephenson County

Lena Brewing Company in Lena. Photo by Michael D. Tedesco.

The beautiful geography of Stephenson County in northwestern Illinois, dotted with rolling hills, beckons travelers to explore the landscape eventually leading to the Mississippi River.

“In Freeport and Stephenson County, we value the outdoor experience,” says Amy Fairweather with the Freeport/Stephenson County Convention and Visitors Bureau. “Stephenson County has endless adventures for everyone from the vast acreage of Krape Park to the rolling hills of our beautiful golf courses to the famous tribute of Little Cubs Field. Hiking, biking, whatever your liking – it’s all in Freeport.”

Fairweather says options for outdoor recreation include major parkland areas like the Oakdale Nature Preserve and the Pecatonica River, which has become more popular for canoeing and kayaking in recent years.

Stephenson County

Water flows through the natural artesian well at Paradise Cove in Winslow. Photo by Michael D. Tedesco.

Sharing a border with Wisconsin, it’s no surprise that the area once boasted the largest number of creameries in the state and still recognizes its dairy heritage with locally made cheeses available across the state. But Fairweather says that’s only a small part of what Stephenson County has to offer.

“With an outstanding location in the heart of the Midwest, Freeport and Stephenson County have a history of innovation, a highly skilled workforce and deliver a robust and diverse work/life balance,” Fairweather says. “We are home to rolling hills, bicycle paths, historic architecture, a beautiful downtown, local craft beer, a stunning park district, award-winning health care facilities, the longest-running amateur theater in the country, a Grammy Award-winning high school music department and a strong sense of community.”

Stephenson County

The Freeport Art Museum, established in 1975, has a large collection of impressive pieces. Photo by Michael D. Tedesco.

The Freeport Art Museum is noteworthy, and history enthusiasts will appreciate area collections like Garnhart’s Oliver Museum in German Valley, which houses an extensive Oliver Hart-Parr agricultural equipment collection. Silver Creek Railroad Museum in Freeport offers rides on an antique steam train, operating between May and October on selected dates. The Stephenson County Historical Museum commemorates Freeport’s rich past in the old mansion of Oscar Taylor built in 1857, once used as a stop on the Underground Railroad. The Cedarville Historical Museum celebrates the life of Cedarville native Jane Addams, founder of Chicago’s Hull House and winner of a Nobel Peace Prize for her humanitarian work.

Stephenson County

Garnhart’s Oliver Museum in German Valley displays vintage farm equipment. Photo by Michael D. Tedesco.

The pride for Stephenson County’s connection to Jane Addams abounds, evidenced by the designation of the Jane Addams Trail, a 17-mile recreational path running from Freeport through Orangeville to the Wisconsin state line. The home where Addams was born and raised still stands in Cedarville, and she is buried in the Cedarville Cemetery.

Another notable historical site is the Black Hawk War monument at Kellogg’s Grove, the site of the final Illinois battle in June 1832. Abraham Lincoln, then a member of the Illinois militia, helped bury five of the soldiers who are honored by the memorial.

Stephenson County

The Lincoln-Douglas Debate Square stands in downtown Freeport. Photo by Michael D. Tedesco.

Lincoln history enthusiasts will also recognize Freeport as the site of one of the seven Lincoln-Douglas debates. Visitors to downtown Freeport can see the spot famous for the debate which established the Freeport Doctrine, addressing states’ rights regarding slavery.

Adjacent to the debate site is a Freeport favorite, the Union Dairy Ice Cream Parlor, serving up ice cream sodas since 1914. Other local tastes throughout the county include Famous Fossil Vineyard and Winery, an old corn crib repurposed as a venue for meetings and weddings.
Travelers can find more local products at Wishful Acres Farm & Brewery, a combined artisan craft brewery and organic farm. Also supporting the area’s agricultural heritage is Lena Brewing Company, which operates in a renovated feed mill. Generations Brewing Company rounds out the three craft breweries located in the county.

Stephenson County

Generations Brewing in Freeport opened in 2014. Photo by Michael D. Tedesco.

Check out Winneshiek Players, the country’s oldest continuously running amateur theater. Or take in a movie at the Lindo Theatre, built in 1922 and designed by world-famous Chicago architects C.W. Rapp and George L. Rapp.

A great first stop is the Freeport/Stephenson County Convention and Visitors Bureau, located on U.S. Highway 20 in Freeport and open seven days a week. For more information, visit

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