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Freeport, IL



Welcome to Friendly Freeport!

Small town living with big business appeal! Freeport has a long, rich heritage which goes back to the mid-19th century. Even our founding father, William "Tutty" Baker and his partners, had commerce in mind when they incorporated the settlement that would be known as Freeport. From its earliest days, Freeport has always been a place where newcomers are greeted warmly and new business is welcomed.

Over the past few decades Freeport has become home to the headquarters, or major divisions, of four Fortune 500 companies. It’s sometimes referred to as the "Hartford of the West" because of the large number of insurance companies that have major underwriting and claims processing facilities within the city limits. Because of this concentration of commerce and industry, Freeport attracts business professionals from across the country. They appreciate the opportunity to experience small town living in an environment where there’s a focus on recreation when the day’s work is done.

Freeport and Stephenson County provide more than 700 acres of parkland; many housing developments centered on lakes or golf courses; and just enough distance to the big cities of Rockford, Chicago, and Madison to make them convenient without daily traffic, noise and congestion problems. Golf, boating, fishing, snowmobiling, and both downhill and cross-country skiing are readily available.

The Freeport Area Chamber of Commerce welcomes you. Feel free to call us anytime; we’re your "one-stop shop" for advice on the Freeport area. We hope you’ll find our midwestern lifestyle to your liking.


Patricia M. Lee

Executive Director

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Freeport is changing. Already home to four Fortune 500 companies or their leading divisions, it is attracting new businesses and industrial firms. These are drawing to the community young and sophisticated professionals and others, who, in turn, are stimulating a dramatic change in the fabric of the community.

As a result, Freeport looks not only to its wealth of history, but to its future as a dynamic city.

Long the commercial hub of Stephenson County, Freeport is seeing rapid growth in its retail sector, as well, providing consumers with a wider range of quality goods at moderate prices. Throughout Stephenson County, large and elegantly styled executive homes are dotting the beautiful wooded hills and valleys that give the area a mark of distinction. In Freeport and the smaller communities of Stephenson County, a broad range of quality housing is available, from comfortable single family homes, townhomes, and condominiums to apartments for young families and senior citizens.

Both public and private school systems excel in their task of educating the young people of the city and county. The Freeport campus of Highland Community College assures easy access to higher education and appropriate training in job skills needed by area businesses and industry. Highland also serves as the local site for classes offered by Columbia College, for those who desire baccalaureate opportunities.

The area’s energetic residents make full use of 780 acres of well-equipped parkland and other recreation facilities in the community. At the same time, they give physical and financial support to the 69 churches and houses of worship in Freeport, alone.


Stephenson County families regularly come together as participants and audience for a lengthy list of festivals and cultural events that fill the area’s social calendar. Ready access to expert medical care is assured through Freeport Memorial Hospital and several area clinics.

The image of today’s Freeport and Stephenson County is an image of exciting change.

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It’s easy come, easy go in Freeport’s transportation network. The city is at the center of a large agricultural area about 25 miles west of Rockford, via U.S. Highway 20. U.S. 20 is a convenient, four-lane divided highway that skirts the community’s northern edge. At Rockford, it links with Interstates 90 and 39, giving Freeport residents easy access to the entire Interstate system. I-90 is the major route between Chicago and Minneapolis-St. Paul. I-39 extends from Rockford to Bloomington where it links with I-74 and I-55. From Freeport, Route 20 continues west to historic Galena, Illinois, and the metropolitan area of Dubuque, Iowa.

Two other highways, State Routes 26 and 75, tie the city with neighboring communities in Stephenson County.

Highway 26 links with I-88 to the south. Route 75 extends northeast to Beloit, Wisconsin, where it intersects with I-43, a route to Milwaukee and Green Bay.

Freeport air travelers drive the short distance to the Greater Rockford Airport, located in the southwest corner of Rockford. The airport is served by Northwest Airlink which connects to more than 400 domestic and international destinations. Limousine service to the airport is available to all residents of Stephenson County.

Eight air freight services also serve the airport, which is 35th in the nation in the number of cargo flights that arrive and depart. It is the second busiest UPS hub in the United States. It is Foreign Trade Zone #176 and a Port of Entry for U.S. Customs.

Freeport’s Albertus Airport is a base for private and corporate aircraft. Located three miles south of the city, the airport accommodates small jets with a 5,500-foot-long paved and lighted runway. Two grass runways, 2,800 and 2,700 feet in length are used by small privately owned planes. The airport offers flight training and charter service. Chicago’s O’Hare International Airport is about 90 minutes from Freeport.

The shipping needs of the city’s business and industry are served by the Canadian National Railroad and by some 50 motor freight carriers. One of the motor freight haulers has a terminal in Freeport.

Taxi service is available in Freeport and the Stephenson County Senior Center provides door to door transportation for the elderly.

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In 1827, German settlers from Pennsylvania began arriving in the Freeport area to make their homes. Among them was William "Tutty" Baker, credited as the founder of Freeport, who built a trading post on the banks of the Pecatonica River. A generous man, Tutty Baker began operating a free ferry across the river and even invited travelers into his home for meals and lodging.

Originally called Winneshiek, the community took its name from the fact of Baker’s renowned generosity – "Free Port" – when it incorporated. Winneshiek was later adopted and is preserved to this day by the Freeport community theatre group. Each August, Freeport remembers Tutty Baker with a joyous festival.

In 1837, Stephenson County was formed and in 1838 Freeport became its seat of government. Linked by stagecoach with Chicago, the community grew rapidly. In 1840, a frame courthouse was erected and the first school was founded. Within two years, Freeport had two newspapers and in 1853 the two were joined by a third which published in German.



By then, the community had a population of 2,000.

On August 27, 1858, the most significant of the historic Lincoln-Douglas debates took place in Freeport and gave the nation direction in succeeding years. Although Douglas won the election and retained his senate seat, his reply to a question on slavery alienated the South, which called it the "Freeport Heresy," and split the Democratic Party. This enabled Lincoln to win the presidency in 1860.

A monument to the debate was dedicated in 1903 by President Theodore Roosevelt and stands at its site. A life size statue recreating the event (pictured here) was dedicated in 1992. Another renowned statue, "Lincoln the Debater," by Leonard Crunelle, is a focal point in the city’s Taylor Park.

The Stephenson County Historical Society preserves local history in "Bohemiana," an Italianate mansion once owned by Oscar and Malvina Taylor

and listed in the National Register of Historic Places. The Taylors devoted their energies to creating an arboretum at the site and today it contains the largest variety of old trees in the county. Also on the property are a Farm Museum, a relocated one-room schoolhouse, and an 1840 log cabin.

The Taylors hosted many guests at Bohemiana, including such well known personalities as Horace Mann, Horace Greeley, Stephenson County native Jane Addams, Edward Everett Hale, and Ralph Waldo Emerson.

Freeport is the birthplace of several celebrities. Among them is Calista Flockhart, the star of the Fox Network’s acclaimed "Ally McBeal" television show. Other noteworthy personalities born in Freeport include Luella Parsons, the famous columnist; Deacon Davis of Harlem Globetrotters fame; and Robert Johnson, founder of BET.


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From a base at Freeport, there is much to see and do in the city, Stephenson County, and all of northwest Illinois – even venturing into southwestern Wisconsin and touching on Iowa.

The Freeport area has many appealing places to stay, from delightful bed and breakfasts and quality hotels to great places for family camping, like Lake Le-Aqua-Na State Park, just north of Lena. The 715-acre park surrounds a 40-acre lake and offers 177 campsites, most with electricity. The park offers swimming, fishing, and boating, plus trails for hiking, biking, and horseback riding.

Stephenson County is home to dozens of restaurants, a generous mix of excellent family dining and fast food outlets, spiced with a few exceptional restaurants catering to ethnic and gourmet diners.

The rich past of the area is everywhere to be seen, from Freeport’s Lincoln-Douglas statue commemorating the second and decisive Debate to Lena’s 1895 water tower, from Freeport’s Bohemiana mansion to the Apple River Fort at Elizabeth, from Freeport’s Old River School Historic District to Kent’s Blackhawk War Monument and the historical museums in Cedarville, Lena, and German Valley.

Antiquers revel in touring the towns and hamlets of Stephenson County and poking around in the many antique shops to be found along the way in places like Lena, Pearl City, and in Freeport itself. Avid shoppers enjoy browsing in Freeport’s downtown district and

nearby shopping centers as well as in the county’s several smaller communities. In Davis, Freeport, and Lena are shops that sell specialty foods: cheese, candy, old-fashioned potato chips, and farm raised beef and pork. Area apple orchards also draw crowds of visitors during their seasons.

On selected weekends in spring and fall, the Fever River Railroad delights whole families in small ways. The amazing HO gauge model railroad measures 103 by 24 feet and is highly detailed, with actual buildings duplicated in miniature along its right-of-way.

For art lovers, the Freeport Arts Center is a genuine treat. The center’s six galleries feature Native American pots, dolls, and baskets; 19th century European paintings and sculpture; Asian decorative arts; Egyptian, Greek, and Roman antiquities; Oceanic ceremonial masks and other pieces; and contemporary art works.



There are special attractions in Stephenson County that amuse and amaze visiting families. A carriage service in Ridott offers rides in an expertly restored antique horse-drawn carriage providing memorable photo opportunities. The naturally flowing artesian well in Winslow has been pouring out thousands of gallons of pure water each day since 1927.

Just beyond Stephenson County are places that are a delight to visit. One is historic Galena, where practically the entire community is listed in the National Register of Historic Places and Main Street is lined with quaint boutiques and excellent restaurants. Straight north of Freeport is Monroe, Wisconsin, the state’s cheese capital. A few minutes west of Galena, visitors can enjoy gaming aboard a riverboat casino.

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The rolling and wooded landscape of the Freeport area has provided builders with the perfect canvas on which to convey their art. Quiet, picturesque home sites are often sheltered in wooded hills, look out on shaded parks or on the sunny fairways of a golf course, or overlook a lake, pond or creek.

Freeport homes range widely in age, size, style, and price. Great homes from the late 19th and early 20th centuries are found along Stephenson Street as it stretches westward between downtown and Park Boulevard. Lining this colorful, tree-shaded thoroughfare are Victorian, Tudor, Federal, Italianate, and other rich styles from the decades surrounding the turn-of-the-century.

Many newer executive style homes dot the hilly area surrounding wooded Krape Park and along the fairways of the Freeport Country Club. More new executive style single family homes are found in the north and west areas of the city, in the vicinity of 36-hole Park Hills Golf Course, and in sparkling subdivisions like Deer Hills, Wildwood Estates, and along Forest Road, in the southwestern part of the community.

Both new and long established areas of the city display a variety of styles: Cape Cods, bungalows, American Foursquares, split-levels, townhomes, condominiums,

and apartments. Cherokee Hills subdivision offers both contemporary townhomes and modern single family homes. Indian Springs combines ranch style duplexes and single family homes. Country Club Condominiums are nestled into a wooded area next to Krape Park and the Freeport Country Club.

Westport Village townhomes, Kiwanis Manor Apartments, Westwind Apartments, and Cheshire Court Apartments line Kiwanis Drive,



near the sprawling and beautiful campus of Highland Community College. Several apartment complexes in Freeport and Stephenson County offer independent living for senior citizens.

In the rural countryside around Freeport, large single family homes share the views with prosperous family farms. The several small communities of Stephenson County offer the same range of homes as are found in Freeport, but in an environment of small town familiarity.

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Tucked away in rural Northwest Illinois, Freeport delights all who come with sights, sounds, and wonders that have lasting appeal.

The Winneshiek Players theatre group has performed a variety of dramas, comedies, and musicals for area residents for more than 70 years. Staged in their own 210-seat theater, Winneshiek Playhouse, the more than 400 members present an annual season of entertainment.

Highland Community College’s jazz band, show choir, community band, and community orchestra perform at the Ferguson Fine Arts Centre. Summerset Theatre productions run on a June through August schedule. The Freeport Community Concert Association presents everything from big band to symphony orchestra, from classical to jazz soloists. The association’s annual season runs from September to April.

All concerts are presented at the 1200 seat theatre of the Masonic Temple in downtown Freeport. Periodically other special entertainment events are also held at the Masonic Temple Theatre.

Each Sunday evening of summer, the Freeport Concert Band offers a free concert at the Krape Park band shell. The Freeport Choral Society presents concerts throughout the year, including a summer pops concert at the band shell.

Movies fans see all the latest Hollywood film releases at downtown Freeport’s eight screen Lindo Theatre.

The Freeport Arts Center is a treat for art lovers. It contains six enriching galleries that include 15th to 19th century painting and sculptures; Egyptian, Greek and Roman antiquities; Native American works and Pre-Columbian artifacts; 17th and 19th century decorative arts from Japan and China; ceremonial masks, pottery, and musical instruments from Oceanic and Southeast Asian cultures; works by contemporary artists, and monthly exhibits of local student artwork. The Art Center’s W.T. Rawleigh collection features one of the best collections of Florentine mosaics in the world. The Philip Dedrick Collection displays Pre-Columbian pottery and Oceanic and African art. The Kenneth Parvin Memorial Collection consists of ancient gold jewelry, Roman glass, and other ancient artifacts.

For history lovers, the city’s Silvercreek Museum offers 25 rooms of memorabilia from the late 1800’s through the 1900’s. They can also take a ride on the Silver Creek and Stephenson Railroad, riding in three antique cabooses and a covered outdoor passenger flat car pulled by a 36-ton, 1912 Heisler steam logging locomotive.

Freeport’s downtown public library is a cultural focal point in the community. The library has nearly 120,000 volumes, plus numerous videos, films, records, audio cassettes, CD’s and other items. It boasts a computer center and a large local history collection. Total annual circulation at the library is in excess of 310,300.

More than a dozen area festivals highlight Stephenson County’s calendar of events. Among the biggest is the Tutty Baker Days Festival, honoring the memory of Freeport’s generous founder. The early August celebration attracts thousands of visitors each year. The festival features live entertainment, an arts and crafts show, food, a beer garden, historic tours, and special children’s rides and activities. A 5K run, a one-mile fun walk, and a sport card show are also parts of Tutty Baker Days in downtown Freeport.

The Stephenson County Fairgrounds is the site of the seven-day Stephenson County Fair, the annual two-day Steam Threshing and Antique Show, and the one day Stephenson County Fibre Art Fair. All three attract big crowds. The County Fair retains the traditional features of county fairs: livestock judging, tractor pulls, country and western entertainers, food, and midway rides.

High school sports enthusiasts fill the stands at home games for the Freeport "Pretzels" and the Aquin Bulldogs. From May through September, stock car race fans pack Freeport Raceway Park for its schedule of races.

Numerous festivals and events take place in the smaller towns of Stephenson County. Pearl City is host to the annual Homecoming Festival in June. Lena holds its Winterfest in mid-January, Stagecoach Trail Festival in June, and Fall Festival in September. In July, German Valley holds its three day German Valley Day celebration. About the same time, Rock City celebrates Rock City Day. In all, close to 125 separate festivals and events are enjoyed each year by Stephenson County residents.

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