A county seat and city of around 24,000, Freeport is couched in the rolling Northwest Illinois countryside.
The population grew suddenly from the 1850s when Freeport became a base for manufacturing. Many of the settlers at this time were German, and Freeport soon became known as “Pretzel City, USA” thanks to a popular bakery founded in 1869.
This heritage is remembered more than 150 years later, and a pretzel is even the mascot for Freeport High School.
In 1858 downtown Freeport hosted the second Lincoln-Douglas Debate, which had lasting repercussions for the 1860 presidential election and the ensuing Civil War.
You can visit the site of this debate and dive into Freeport’s rich culture and past at attractions like the Stephenson County Historical Society Museum and the vibrant Freeport Art Museum.
1. Stephenson County Historical Society Museum and Arboretum
The history of Freeport and Stephenson County comes alive at this riveting museum, couched in a charming three-acre arboretum with specimen trees and gardens.
The center of attention on this campus is the 1857 Taylor House, thought to have been part of the Underground Railroad during the Civil War.
The house is built from rusticated, locally quarried limestone and belonged to Oscar Taylor who was the son of a Speaker of the House of Representatives, and opened Freeport’s first bank.
The basement is believed to have been a hiding place for fugitive slaves, and a secret door for this purpose is still intact in the basement.
There’s much more to check out on the grounds, like an historic schoolhouse, a museum preserving industrial artifacts, a museum for the cast-iron Arcade toys manufactured in Freeport and a log cabin dating to the mid-19th century.
2. Lincoln-Douglas Debate Square
In 1858 a seismic historical event happened in downtown Freeport. Here, the second of seven debates took place between Abraham Lincoln and incumbent Stephen Douglas in the run up to the United States Senate elections.
Slavery was the most prominent topic, and it was in this debate that Douglas articulated his Freeport Doctrine.
This damaged his standing in the South and ultimately split the Democratic Party, paving the way for his defeat (and Lincoln’s Victory) in the later Presidential Election in 1860.
The site of the debate has interpretive waysides explaining this momentous event, as well as a lifesize monument of the two men, installed in 1992.
3. Krape Park
This refined, award-winning park is on the banks of Yellow Creek, southwest of downtown Freeport.
Set in century-old woodland, Krape Park has some striking features, like a 44-foot waterfall tumbling down a limestone cliff and an elegant white bridge from 1919.
In summer you can rent a canoe or paddle boat for a trip along the creek, and by the water is the Yellow Creek Adventure Golf Course, open Memorial Day weekend through September.
The Koenig Amphitheatre stages outdoor concerts and festivals throughout the season, and in September is an anchor for Art in Park, brimming with art booths and live music.
Some of the wealth of other attractions at Krape Park include a unique vintage carousel, an 18-hole disc golf course, tennis courts and sledding hills and cross-country ski trails in winter.
4. Freeport Art Museum (FAM)
The Freeport-based industrialist William Thomas Rawleigh (1870-1951) traveled the world and amassed a diverse art collection with the purpose of bringing the world to the doorstep of his hometown.
That collection formed the basis for the Freeport Art Museum, founded in 1975 and housed in a palatial former school building from 1911.
FAM hosts important traveling exhibitions and curates its own shows, drawing from its impressive collection spanning 4,000 years.
There’s something new to see every eight to ten weeks at the Ferguson and Newell Galleries, while there’s a gallery upstairs for work by talented local solo artists, groups and students. The museum is community oriented, with dynamic public programs for all ages.
5. Read Park
A recreation honeypot, Read Park is full of sports and leisure amenities for all ages. This is the home of the Freeport Park District administration office, and the park’s pavilion hosts many park district programs, like painting, Tai Chi and martial arts.
Within the park’s boundaries is Freeport’s premier skate park, as well as the Read Park Family Aquatic Center, offering a large zero-depth pool, slides, spray features and more.
Close to the pavilion are softball fields, basketball courts and a children’s playground, while there’s a set of tennis courts on the south side along Empire Street.
On the southwest corner is the remarkable Little Cubs Field, a one-third size replica of Wrigley Field, even featuring ivy, bricks, dirt and sod from the original stadium.
Available for rental, this field is used mostly for little league games, but you also take a look around for free and admire the attention to detail.
6. Union Dairy
When the cherished Union Dairy opened in 1914, Stephenson County had more creameries than anywhere else in Illinois.
The dairy gained its name through a merger or union with a rival dairy. Then in 1934, after moving to its current location on the Lincoln-Douglas Debate Square, Union Dairy started to produce the ice cream that would make it famous.
The parlor has always been known for its innovation, and the popular Orange Pudding is one wacky flavor that has made it through to the present.
The menu is bursting with tempting treats, from sundaes to surprising scoop combinations, shakes and cakes, and also serves all beef Chicago-style hot dogs, sandwiches, burgers and a big choice of sides.
7. Jane Addams Recreation Trail
With gentle rolling hills, prairie, oak woods, creeks and wetlands, the countryside in Freeport’s backyard deserves some exploration.
A great way to do this is on the 17-mile Jane Addams Recreation Trail, named for the Nobel Prize-winning political activist and reformer, who was born close by in Cedarville in 1860.
You can pick up the trail at Tutty’s Crossing Trailhead in downtown Freeport and head off on a memorable journey north to the Wisconsin border where the path merges with the 40-mile Badger Trail, extending to Madison, WI.
You’ll never be far from a watercourse on the route, and there are 22 bridges to cross, like the Van Buren Bridge (1885) on the Pecatonica River, and a charming old covered bridge outside Orangeville.
8. Silver Creek & Stephenson Railroad & Museum
An enthralling piece of railroad history has been preserved just south of Freeport. Here you can experience steam branch-line railroad on a 3.4-mile stretch of track along the former Milwaukee Road, pulling away from the Silver Creek Depot.
Drawing a set of historic cabooses along this track is a 36-ton Heisler steam locomotive. If this is out of order, the museum also has a fleet of more modern diesel alternatives.
Every few months there are seasonal rides down the track, like the spooky Train of Terror in October.
Close by is the Silver Creek History Museum, on the site of a large former poorhouse from 1902, turned into a sheltered care home later in the 20th century.
You’ve got 28 rooms of local history to browse, and the most impressive exhibit is a 130-ton stationary engine still in working order.
9. Park Hills Golf Course
This highly rated public golf facility has two 18-hole courses in an idyllic undulating landscape. Both courses are relatively short, but with some unforgiving rough so you’ll need to be precise and think carefully about risk vs reward on these tracks.
True to its name, Park Hills has hilly terrain to contend with, especially on the West Course (slope rating of 121), which has six or so uphill holes that play a club longer.
You can practice your swing at the 300-yard driving range, which has natural grass tees and 15 hitting stations, while the pro shop stocks any piece of equipment you might be missing.
10. Oakdale Nature Preserve
The Freeport Park District manages this calming slice of nature, outside the city around five miles south of downtown.
On 133 acres, the Oakdale Nature Preserve blends forests, stream habitats and prairie. Being away from the city, the preserve is never crowded and has four miles of trails for hiking, dog walking and bicycling, as well as a ⅓-mile accessible trail.
You’ll find interpretive signs along the trails, along with a picnic area and fire pit.
11. Wishful Acres Farm & Brewery
About ten miles out into the gently rolling Northwest Illinois countryside is a small-batch brewery operating on a family farm.
The farm grows more than 100 varieties of vegetables, fruits, herbs, micro-greens, hops and garden plants, all pre-sold via its CSA program.
The craft brewery was founded here in 2016 and has a taproom and bar on-site where you can sample 12 on draft and choose your favorites to take home in 22-oz bottles and growlers.
The beer list changes by the week and well over 100 different varieties have been produced since the brewery opened. Where possible the ingredients, from hops to flavorings, are grown right here on the farm.
12. Children’s Hands-On Museum of Northwest Illinois
At the Freeport Lincoln Mall there’s a great children’s museum with more than 6,000 feet of interactive space in a labyrinthine building.
The ever-changing exhibits help children and families explore, learn and create through interactivity. The museum handles subjects like science, technology, engineering and math (STEM), social sciences, art, drama and music.
Children can also roleplay professions and everyday situations, at a restaurant, medical clinic, farm and more. There are two rooms especially designed for tots, as well as a sensory room for children with disabilities.
13. Taylor Park
The land for the original park of the Freeport Park District was acquired as long ago as 1905. On Freeport’s northeast shoulder, Taylor Park is the third-largest in the city, and harks back to a horse track used for trotting races.
The completely flat terrain is a holdover from that time, as is the roughly oval trail encircling many of the park’s sports amenities.
Taylor Park’s three lighted softball fields host the Park District’s highly competitive adult leagues and tournaments, and there are also 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 thought to be the oldest continuously operating amateur theater company in the country.
The company has produced a season of performances every year, since 1926 and moved to its current location downtown in 1936.
This venue has been updated over the years, with extensions in the 1940s and remodeling in the 60s and 80s.
Holding audiences of up to 216, the Winneshiek Playhouse is a fine place to watch the company’s plays and musicals, selected to appeal to all tastes.
Recent productions have included 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
Strategically located a few miles out of Freeport on Highway 20, this visitor center is a useful introduction to Stephenson County and its many attractions and amenities.
The welcoming and knowledgeable staff will be happy to provide directions and information about local history, tours and guides, accommodations, restaurants and the many activities available in the county.
There’s also a shop at the center stocking locally made gifts, from artisan cosmetics to t-shirts, jewelry and handmade Christmas decorations.