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Visit Downtown Freeport

Visit Downtown Freeport

A destination on its own, Downtown Freeport features authentic architecture, diverse dining options, abundant shopping, family attractions, and historic monuments to keep all ages engaged.

two young girls are playing in a fountain at the Freeport Art Plaza splash pad

With entertainment venues, outdoor adventures and historic sites set around a revitalized, walkable downtown, Freeport is home to exciting attractions for all ages. Take a walk down Chicago Avenue and explore the fascinating locations that define the community of Freeport. 

Explore our Attractions

a group of young women holding shopping bags walk down a street in downtown Freeport

The downtown shopping experience continues to impress with vibrant boutiques, exquisite fine and antique jewelry, home decor and furniture, confectioneries, hobby memorabilia and more. Make time to stroll the streets for impressive finds you will be raving about to all of your friends.

Explore our Shops

a sandwich and french fries in a basket

Mouthwatering burgers. Sweet and savory BBQ. Tempting treats. You may arrive hungry in Freeport, but with a wide menu spanning a world of tastes, you’re sure to find a new favorite and leave satisfied — or possibly clamoring for seconds. Check out the restaurants, diners and eateries around Freeport and find your favorite flavors.

Explore our Dining

Chicago Avenue is practically a venue of its own with cruise-ins, beer tasting and live music drawing crowds to revel and celebrate in our streets. Check out our calendar and plan your weekends around these can’t-miss happenings.

Explore our Events


an illustrated map of downtown Freeport, highlighting the locations of various attractions

Chicago Avenue

Spanning the heart of downtown Freeport, Chicago Avenue has long been an artery of activity in the city. Today, the newly renovated Chicago Avenue provides a safer, more vibrant atmosphere for both pedestrians and bicyclists alike. Brand-new streetlights, pedestrian-friendly intersections and a completely revamped sidewalks make this ever-popular corridor a pleasant destination for shopping and entertainment as well as a cultural center for our community!

Photo of the Winneshiek Playhouse

228 W Clark St.

Hailed as one of the oldest, continuous all-volunteer amateur theatres in the nation, Winneshiek Playhouse in downtown Freeport is an organization of people devoted to the development and enjoyment of theatre arts since 1916. In over a century, hundreds of first-rate productions of comedy and dramas have been performed within the historic walls of this charming venue. Visit their website for the full list of upcoming productions so you can experience the artistry for itself!

photo of the Freeport Public Library

100 E Douglas St.

Freeport Public Library believes that in many ways a library is like a community living room: a dynamic resource and welcoming destination where people can learn, grow and assemble throughout their lives. Contemporary libraries like this one help individuals and entire communities remain vital and energetic. Freeport Public Library is home to a large collection of book titles (over 110,000), meeting rooms, diverse programs and much more. This library is more than books on a shelf, it’s a meeting place to share culture, history and community.

Lincoln statue in Debate Square

114 E Douglas St.

On August 27, 1858, the most significant of the historic Lincoln-Douglas debates took place in Freeport, IL and gave the nation direction in succeeding years due to the famous Freeport Doctrine. While Stephen Douglas kept his seat in the Senate after the debates, his reply that each state should be perfectly free to do as it pleased in regards to slavery, no matter the ruling of the Supreme Court, stirred a sentiment of betrayal among constituents that would come back to haunt him in his bid for President in the election of 1860. Abraham Lincoln’s point that “a house divided could not stand,” his belief that Americans of every race were entitled to “life, liberty and the pursuit of happiness,” and his stance against Douglas’ advocacy for popular sovereignty were what ultimately led to his election later on.

Visit the Lincoln-Douglas Debate Square in historic downtown Freeport, next to the Union Dairy, to see the first statue ever erected to include both Lincoln and Douglas in commemoration of the debates that influenced US history. This landmark is one of two points of interest for Lincoln history in Stephenson County.

Entrance to the Union Dairy Farm

126 E Douglas St

If you’re looking to find a little old school cool, stop down to the Union Dairy for a taste of the classic 50’s malt shop experience. Sit at the parlor bar for a juicy burger and a shake or order ice cream to go and enjoy the scenery of the Lincoln-Douglas Debate Square and historic Downtown Freeport.

Entrance to the Freeport Art Plaza

15 W. Chicago Ave.

The Freeport Art Museum has created a vibrant, arts-based civic space that continues to add beautiful features to welcome residents and visitors to downtown. Complete with a family splash pad, performance stage and large green space, the park is centrally located to Lincoln Douglas Debate site as well as Union Dairy.

entrance to the Lindo Theatre

115 S Chicago Ave.

Located in historic Downtown Freeport, the Classic Cinemas Lindo Theatre began with a single screen, a stage for vaudeville acts and a Bennet pipe organ to accompany the films. Over the years, this historic landmark has transformed into 9 stadium auditoriums equipped with Digital 3D and Enhanced 4K Digital Projection and 7.1 Sound. Grab a snack at the concession stand upfront and enjoy one of the latest movie releases in their spacious and comfortable theaters.

Tutty's Crossing

7. Pecatonica River + Tutty’s Crossing Trailhead

250 E Stephenson St.

Tutty’s Crossing Trailhead, located along the Pecatonica River in historic downtown Freeport, has been revitalized through community initiatives. Originally the location of the Burgess Battery Company (better known now as Duracell), Tutty’s Crossing has become the central spot for many biking and walking paths since connecting the Jane Addams Trail and Pecatonica Prairie Trail in 2015. Walk, bike, fish or paddle – this recreational area is perfect for experiencing the great outdoors in Freeport, Illinois

Feast your eyes on the architectural details from buildings over 100 years old as you step back in time and tour scenic downtown Freeport at your own pace. These historical buildings are steeped in significance to the growth of Freeport and northern Illinois. Learn more about each building and find locations with the help of our free walking tour app.


Pub 219

219 E Stephenson St

Joe’s Pizza

23 W Stephenson St

La Jarocha

21 W Stephenson St

Union Dairy

126 E Douglas St

9 East Coffee

9 East Stephenson St

Capybara Café

100 E Douglas St

Galena Supermarket

207 S Galena Ave

The Wagner House

1 E Spring St


306 N Galena Ave

Hilldale Deli

30 W Stephenson St

Landmark Restaurant

1 E Main St

Mort’s Bar & Grill

114 S Chicago Ave

This Is It Eatery

109 S. Galena Ave

The Cookie Jar

12 E Stephenson St


American Garage Art

22 W Spring St

Amity’s Attic Resale

22 E Main St

Ashley Jackson Beauty

6 E Stephenson St

Christian Supply Store

23 E Stephenson St

The Clothes Bin

15 E Stephenson St

Deininger Floral

1 W Main St

Down’s Shoe and Orthopedic Service

12 E Stephenson St

Dream Day Designs

30 W Spring St

Eileen’s Gems

222 W Stephenson St

Flair Boutique

14 E Stephenson St

Frank Jewelers

19 E Stephenson St

Jennings Cards

18 W Stephenson Ave

Jet Beauty Mart

5 W Stephenson Ave

Linda Vietmeyer Studio/Gallery

7 E Stephenson Ave

Kyah Jewelry

24 W Stephenson Ave

Luecke Jewelers

10 E Main St


222 W Stephenson Ave

Radiance Beauty Lounge

120 S Chicago Ave

Re-Spun Records & Resale

24 W Stephenson St

Rite-Way Furniture & Appliance

20 E Stephenson St

Rootz and Branchez

101 W Main St

Royal Oak Antiques

101 E Spring St

Sports Rec. & Apparel

7 E Main St

Stacey McDonald Pottery

12 W Spring St

Swank & Mercier Boutique

1 E Spring St

T&D Toy & Hobby

116 S Chicago Ave

The Langley Co.

4 E Stephenson St

The Space Salon

2 E Stephenson St

Twice As Nice Consignments

8 W Stephenson St

Twice As Nice Home

24 E Stephenson St

The Wagner House Great Debate Boutique

1 E Stephenson St

Wagner Office Supply

10 W Main St


Pretzel Fest – April 27, 2024

Pretzel City Winefest – May 11, 2024

Music on Chicago – June 7, 2024

Music on Chicago – July 5, 2024

Tutty Baker Fest – July 12-14, 2024

Music on Chicago – August 2, 2024

Cruise Night – August 10, 2024

Paint the Port – August 23, 2024

Eats & Beats – August 23-24, 2024

Pretzel City Brewfest – September 28, 2024

Wine & Witches – October 11, 2024

Bootiful Saturday – October 26, 2024

Mistletoe Walk – November 23, 2024

Small Business Saturday – November 28, 2024

Key Industries

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Construction, Plumbing, Heating, & Service

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Private Label Food Manufacturing

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