Top 15 Attractions and Activities in Freeport, Illinois

A county seat and city of approximately 24,000 residents, Freeport is situated within the picturesque Northwest Illinois countryside.

The population surged beginning in the 1850s when Freeport emerged as a manufacturing hub. Many settlers during this period were of German descent, leading Freeport to earn the nickname “Pretzel City, USA,” attributed to a well-regarded bakery established in 1869.

This cultural legacy persists over 150 years later, with a pretzel serving as the mascot for Freeport High School.

In 1858, downtown Freeport was the site of the second Lincoln-Douglas Debate, an event that had profound implications for the 1860 presidential election and the subsequent Civil War.

The location of this debate can be visited, alongside an exploration of Freeport’s rich history and culture at venues such as the Stephenson County Historical Society Museum and the vibrant Freeport Art Museum.

1. Stephenson County Historical Society Museum and Arboretum

The narrative of Freeport and Stephenson County is richly conveyed at this captivating museum, set within a scenic three-acre arboretum featuring diverse specimen trees and gardens.

The focal point of this location is the Taylor House, constructed in 1857, believed to have served as part of the Underground Railroad during the Civil War.

The house, made from locally-sourced rusticated limestone, belonged to Oscar Taylor, son of a former Speaker of the House of Representatives, who founded Freeport’s first bank.

The basement is thought to have been a refuge for fugitive slaves, with a secret door still intact.

Additional highlights on the grounds include a historic schoolhouse, a museum showcasing industrial artifacts, an exhibition dedicated to the cast-iron Arcade toys produced in Freeport, and a mid-19th century log cabin.

2. Lincoln-Douglas Debate Square

In 1858, a monumental historical event transpired in downtown Freeport when the second of seven debates took place between Abraham Lincoln and incumbent Stephen Douglas as they vied for the United States Senate seat.

Slavery emerged as the dominant topic, during which Douglas articulated his Freeport Doctrine. This assertion adversely affected his standing in the South, ultimately fracturing the Democratic Party and facilitating Lincoln’s success in the Presidential Election of 1860.

The debate site features interpretive waysides detailing this significant event, accompanied by a lifelike monument of both orators, established in 1992.

3. Krape Park

This refined and award-winning park is nestled along the banks of Yellow Creek, located southwest of downtown Freeport.

Situated within century-old woodlands, Krape Park boasts remarkable features, including a 44-foot waterfall cascading down a limestone cliff and a beautifully designed white bridge from 1919.

During the summer season, visitors can rent canoes or paddle boats for a leisurely trip along the creek. Adjacent to the water is the Yellow Creek Adventure Golf Course, operational from Memorial Day weekend through September.

The Koenig Amphitheatre hosts outdoor concerts and festivals throughout the year, with September featuring the Art in Park event, which is filled with art booths and live music.

Krape Park offers a myriad of attractions, including a distinctive vintage carousel, an 18-hole disc golf course, tennis courts, and opportunities for sledding and cross-country skiing in winter.

4. Freeport Art Museum (FAM)

The Freeport-based industrialist William Thomas Rawleigh (1870-1951) traveled extensively, amassing a diverse art collection intended to bring the world to his hometown.

This collection became the foundation of the Freeport Art Museum, established in 1975 within an elegant former school building from 1911.

The museum features significant traveling exhibitions and curates its own displays, highlighting its impressive collection that spans 4,000 years.

Regularly changing exhibits are presented every eight to ten weeks in the Ferguson and Newell Galleries, while an upstairs gallery is dedicated to showcasing works by local solo artists, groups, and students. The museum is engaged with the community, offering dynamic public programs for attendees of all ages.

5. Read Park

A recreational hub, Read Park offers a plethora of sports and leisure amenities for all age groups. It houses the Freeport Park District administration office, and its pavilion is the venue for a variety of park district programs, including painting, Tai Chi, and martial arts.

Included within the park is Freeport’s premier skate park, as well as the Read Park Family Aquatic Center featuring a large zero-depth pool, slides, and spray features.

Nearby the pavilion are softball fields, basketball courts, and a children’s playground, while tennis courts can be found on the south side along Empire Street.

In the southwestern corner resides the impressive Little Cubs Field, a one-third scale replica of Wrigley Field, complete with ivy, bricks, dirt, and sod sourced from the original stadium.

This field, available for rental, is primarily utilized for little league games, yet visitors can freely explore and appreciate its intricate details.

6. Union Dairy

Upon its establishment in 1914, Union Dairy became a beloved institution, coinciding with Stephenson County housing more creameries than any other location in Illinois.

The dairy acquired its name following a merger with a competing dairy. Subsequently, in 1934, after relocating to its current position on Lincoln-Douglas Debate Square, Union Dairy commenced the production of its renowned ice cream.

The parlor has earned recognition for its creativity, exemplified by the whimsical Orange Pudding flavor that remains popular to this day.

The extensive menu features an array of delectable options, including sundaes, unique scoop combinations, shakes, and cakes, alongside all-beef Chicago-style hot dogs, sandwiches, burgers, and a wide selection of sides.

7. Jane Addams Recreation Trail

The countryside surrounding Freeport, characterized by gentle rolling hills, prairies, oak woods, creeks, and wetlands, invites exploration.

A fantastic method to experience this is by traversing the 17-mile Jane Addams Recreation Trail, named in honor of the Nobel Prize-winning political activist and reformer, who was born nearby in Cedarville in 1860.

This trail can be accessed at Tutty’s Crossing Trailhead in downtown Freeport, leading north toward the Wisconsin border, where it connects with the 40-mile Badger Trail extending to Madison, Wisconsin.

Along this route, one is never far from a waterway, and it includes 22 bridges to cross, such as the Van Buren Bridge (1885) over the Pecatonica River, as well as a charming covered bridge located just outside Orangeville.

8. Silver Creek & Stephenson Railroad & Museum

An intriguing segment of railroad history has been preserved just south of Freeport. Visitors can experience a steam branch-line railroad operating on a 3.4-mile stretch of track along the former Milwaukee Road, departing from the Silver Creek Depot.

A 36-ton Heisler steam locomotive pulls a collection of historic cabooses along this line. Should this locomotive be out of service, the museum maintains a selection of modern diesel alternatives.

Seasonal rides, such as the spine-tingling Train of Terror in October, are available for guests.

Nearby is the Silver Creek History Museum, located at the site of a large former poorhouse from 1902, later converted into a sheltered care home in the latter part of the 20th century.

This museum features 28 rooms of local history, with the centerpiece being a 130-ton stationary engine that remains operational.

9. Park Hills Golf Course

This highly-rated public golf facility features two 18-hole courses set in a picturesque undulating landscape. While both courses are relatively short, they present challenges due to some unforgiving rough, necessitating precision and strategic risk assessment.

True to its name, Park Hills presents hilly terrain, especially on the West Course (slope rating of 121), characterized by approximately six uphill holes that play longer.

A 300-yard driving range with natural grass tees and 15 hitting stations allows players to practice their swings, while the pro shop stocks a variety of equipment for any needs.

10. Oakdale Nature Preserve

Managed by the Freeport Park District, this tranquil area of natural beauty is located approximately five miles south of downtown.

Spanning 133 acres, the Oakdale Nature Preserve intersperses forests, stream habitats, and prairie landscapes. Due to its distance from the urban center, it is typically uncrowded and features four miles of trails suitable for hiking, dog walking, and cycling, in addition to a ⅓-mile accessible trail.

Interpretive signage is present along the trails, which also include a picnic area and fire pit.

11. Wishful Acres Farm & Brewery

Located about ten miles into the gently undulating Northwest Illinois countryside, this small-batch brewery is situated on a family-run farm.

The farm cultivates over 100 varieties of vegetables, fruits, herbs, micro-greens, hops, and garden plants, which are primarily pre-sold through its CSA program.

This craft brewery was established in 2016 and features an on-site taproom and bar, presenting 12 draft options for patrons to sample, along with the ability to select favorites to take home in 22-ounce bottles and growlers.

The beer selections rotate weekly, with over 100 different varieties having been produced since the brewery’s inception. Ingredients, whenever feasible, are sourced directly from the farm.

12. Children’s Hands-On Museum of Northwest Illinois

Located within the Freeport Lincoln Mall, this interactive children’s museum spans over 6,000 square feet within an intricately designed building.

The engaging exhibits continuously transform, promoting exploration, learning, and creativity through hands-on experiences. Topics cover a wide spectrum, including science, technology, engineering, and math (STEM), social sciences, art, drama, and music.

Children have the opportunity to role-play various professions and everyday scenarios, including settings like restaurants, medical clinics, farms, and more. Two rooms are specifically designed for younger children, alongside a sensory room dedicated to children with disabilities.

13. Taylor Park

The land for the original park of the Freeport Park District was secured as early as 1905. Situated on Freeport’s northeast side, Taylor Park ranks as the third-largest park within the city and is a remnant of a historical horse racing track.

The park features flat terrain, a legacy of its racing origins, as well as a roughly oval trail encircling many of its sports facilities.

Three lighted softball fields at Taylor Park accommodate the Park District’s intensely competitive adult leagues and tournaments. Additionally, there are tennis courts, basketball courts, a concession stand, a statue of Lincoln from 1929, and a picnic shelter.

14. Winneshiek Playhouse

Established in 1916, the Winneshiek Players is recognized as one of the oldest continuously operating amateur theater companies in the nation.

The company has consistently produced a seasonal array of performances since 1926 and relocated to its current downtown venue in 1936.

Over the years, this venue has undergone enhancements, including extensions in the 1940s and renovations in the 1960s and 1980s.

The Winneshiek Playhouse, accommodating up to 216 attendees, serves as a splendid venue for enjoying the company’s plays and musicals, which are selected to appeal to diverse audiences.

Recent productions have featured titles such as The Rocky Horror Picture Show, Leading Ladies (Ken Ludwig), Witness for the Prosecution, and Six Dance Lessons in Six Weeks (Richard Alfieri).

15. Stephenson County Visitor Center

Conveniently situated a few miles outside of Freeport along Highway 20, this visitor center provides valuable insights into Stephenson County and its various attractions and offerings.

The welcoming and knowledgeable staff are available to furnish directions and information regarding local history, tours, accommodations, restaurants, and the multitude of activities available throughout the county.

The center also features a retail shop offering locally crafted gifts, from artisanal cosmetics to t-shirts, jewelry, and handmade holiday decorations.