Freeport Refreshed

As Freeport leaders and citizens unite in revitalizing their hometown, here are 5 ways to rediscover the Pretzel City.

Freeport is a small city with a lot to offer.

Known by locals as the Pretzel City, thanks to the loads of pretzels made by a famous bakery here in the 1850s, Freeport is a hub for Stephenson County, both as its largest city and its county seat.

Freeport’s industrial history has brought some challenges over the past few decades, but more recently the trend is reversing and Freeport has much to celebrate. This “new” Freeport fully embraces its industrial and agricultural roots while advancing forward with new businesses, scenic destinations and a rich food-and-drink scene that pays true homage to the past.

If it’s been awhile since you last explored this “small” city, it’s high time to play tourist once again.

“Freeport is the perfect size for having a small-town experience while still having access to amenities and culture to surround yourself with,” says Nicole Haas, brand director for the Greater Freeport Partnership. “It’s a community that has seen a lot of revitalization from people who are returning to the area and are seeing the vigor and the possibility of what this area, region and city can be. We’ve had more than a dozen new businesses open in downtown Freeport in the past year.”

With small businesses booming, downtown arising and numerous historical pulls there’s never been a better time to check out the city’s gems, both new and old.

Here are 5 ways to make the most of an adventure through Freeport and its surrounding area.

New businesses are popping up in downtown Freeport. (Greater Freeport Partnership photo)

1. Downtown Shopping

Those who enjoy shopping may be surprised to learn what they can find in downtown Freeport.

“We have more than 25 downtown shopping and service businesses in Freeport,” says Angie Swank Spachman, who co-owns downtown boutique Swank and Mercier with Ginger Mercier. “You can definitely spend a day shopping.”

Some Freeport businesses have long-standing histories that go back decades.

Take Luecke Jewelers, 10 E. Main St., which celebrates its 100th anniversary this year. Stewart Centre, which celebrates 50 years, is an 80,000-square-foot building with roughly 30 tenants, including attorneys, government officials and other business professionals.

However, the 12-story “high-rise” adds to the character of the downtown, which is what has drawn new business owners like Ashley Jackson, owner of Ashley Jackson Beauty, 6 E. Stephenson St.

“It’s been my dream to have my own space,” says the former hair stylist, who grew up in the area. “There’s always something going on downtown, so being in the mix is exciting.”

Jackson, who opened her doors in August, offers permanent makeup solutions like microblading, henna-stained eyebrows, and lash lift and tint. She also provides space for Dr. Jen Yeager, who has her own medical aesthetics practice in Beloit and offers Botox and injectables in Freeport.

“I can’t tell you how many people have told me, ‘You’re such a great addition to this town,’” Jackson says.
The way many downtown businesses share spaces and mix their offerings is just another unique feature of Freeport, says Spachman.

The Wagner House, 1 E. Spring St., for example, is a three-story wedding and event venue that also plays host to a restaurant/bar and wine bar – which frequently showcase live musicians – and Spachman’s boutique, which features trendy and affordable clothing, jewelry, accessories and gifts.

“Wagner House is a place where you can have a signature drink, eat lunch or dinner, and shop at our boutique,” Spachman says. “It’s such a unique shopping experience, all tucked inside this beautiful old building that used to be a printing company.”

Other new businesses include Rootz and Branchez, a metaphysical store, and Sweet Littles Children’s Boutique and Portrait Studio.

2. Restaurants and Breweries

If you’re heading to Freeport for a day of shopping, you might as well stay for a hot meal and a cold drink.
A large handful of restaurants are old-time favorites, like Union Dairy, 126 E. Douglas St., which is in its 107th year of business.

The dairy-turned-ice cream parlor graduated to a full grill menu in 2005, but you’ll have to stop by before the end of October to grab a burger and ice cream treat. Union Dairy shuts down for winter.

Mrs. Mike’s Potato Chips, 70 E. Monterey St., celebrates its 50th anniversary this year, and it’s the perfect place to grab snacks for a day of shopping. The shop supplies patrons and local restaurants with signature old-fashioned, kettle-style chips, popcorn and pretzels.

Classic pizza places include Bourbons on Main, 109 S. Galena Ave., and This Is It Eatery, 16 N. Chicago Ave.
Not to be missed are the many new restaurants popping up downtown.

Stephenson St. Pretzels and Italian Ice, 12 W. Stephenson St., opened in August and offers fresh, homemade pretzels made daily – a fantastic tribute to the city’s pretzel roots.

“Freeport was settled by Germans, and there’s still a lot of German heritage in this area,” Haas says. “Freeport also was home to more breweries than Milwaukee in the mid- to late-1800s. Along with the consumption of beverages, there needed to be something to soak them up, and with our German heritage, that was pretzels. Billerbeck Bakery made pretzels for the area as the snack food to go along with the breweries we had.”

Munchies Cereal and Shake Bar, 23 W. Exchange St., also opened in August and offers a fun array of ice cream sundaes, shakes and cereal combinations.

“My daughter loves Munchies,” says Spachman. “It’s something different for all ages – people love adding their favorite cereals and toppings to their shakes. Munchies also serves lunch, but our favorite so far is the desserts.”
The Drive-Thru, 1521 S. West Ave., – which, as the name suggests, doesn’t have indoor dining, only drive-thru service – offers simple, fast options like burgers, steak sandwiches and chicken strips.

The kicker is that The Drive-Thru, which opened this May, offers up to 15 free toppings on its burgers, from ketchup and mustard to grilled mushrooms or a fried egg.

The Freeport area also is home to three craft breweries, all owned by locals and all within a 10-mile stretch of each other.

Generations Brewing Co., 1400 S. Adams Ave., was founded in 2014 and kicked off a resurrection of craft brewing.

Not long after Generations started serving beer, two more breweries opened: Wishful Acres Farm and Brewery, 4679 N. Flansburg, in nearby Lena, Ill., and Lena Brewing Co., 9416 W. Wagner Road, in Lena.

3. Krape Park

Freeport’s No. 1 tourist destination is an outdoor gem called Krape Park, 1799 S. Park Blvd.

The park dates back to 1913, when the Freeport Park District bought the 120-acre property from Dr. W.W. Krape with the stipulation that the park be named after the dentist as long as it was used for recreational purposes, says Schneider.

“The natural landscape of the park is part of what makes it so interesting,” says Ron Schneider, executive director of the Freeport Park District. “There is a creek that winds its way through the park, and there are natural limestone bluffs and formations. Back in the 1930s, there were government-funded projects that enhanced certain areas of the park. They created a 44-foot waterfall, and at the top of this bluff you can overlook the park.”

Visitors can muse over flower gardens and public art pieces or utilize six paved walking and biking trails that range from a quarter-mile to just over a mile in length.

There’s also an 18-hole disc golf course, the Kids Kastle playground, a Little Kids’ Playground, several picnic shelters, an outdoor amphitheater and a baseball field. New tennis and pickleball courts will be completed soon.
“It’s a unique place,” says Schneider. “We’re always trying to stay on top of the latest activities and trends for recreation. Our parks are very important to our residents, and we understand how important they are to drawing visitors.”

Recent improvements at Lake Le-Aqua-Na State Park, in nearby Lena, Ill., have made the area more accessible to hikers and campers. The Jane Addams Trail is a few miles away, and it’s prime for biking. Freeport’s connection to the Lincoln-Douglas debates is commemmorated in Debate Square downtown. (Left: Le-Aqua-Na State Park photo. Top Right: Freeport Park District photo.)

4. Timeless Trails

One of the most timeless things you can do in Freeport is to take advantage of its trails.
Oakdale Nature Preserve, 4433 S. Cranes Grove Road in Freeport, is a favorite among locals.
Owned by the Freeport Park District and located on the city’s southeast side, this 133-acre preserve is a beautiful spot for viewing fall colors.

“Oakdale is a breath of fresh air,” says Schneider. “It’s meant for outdoor recreation, to enjoy the nature that’s there through the hiking or biking trails. It’s a great place to come and relax and spend some time outdoors.”

More than 4 miles of hiking and biking trails wind through woods and open prairie. Recent improvements to the park include a newly paved quarter-mile path. Work continues on a new nature-based playground, picnic shelter, trail improvements, enhanced parking and a new bathroom.

If you’re more into biking, try using the nearly 19 miles of the Jane Addams trail that run from historical Tutty’s Crossing in downtown Freeport all the way to the Wisconsin state line, where it becomes the Badger State Trail and continues 40 miles north to Madison (a Wisconsin state trail pass is needed north of the border).

The beginning of the Jane Addams Trail brings you past life-size statues that mark the site of the second Lincoln-Douglas debate of 1858.

After that, the trail follows an old line of the Illinois Central Railroad. There are multiple trail heads along that route, so riders don’t have to complete the entire trail in one day.

“It’s flat, and it’s extremely beautiful,” says Haas. “It’s both paved and unpaved and well-known by bikers. It would be the perfect natural experience to enjoy leaf viewing when all you hear is the rustle of the leaves themselves.”

Not too far away is the newly reopened Lake Le-Aqua-Na State Park near Lena, Ill. The 715-acre state recreation area has a 10.5-mile multi-use trail system available to hikers, bikers and equestrians.

“Some trails go through planted pine portions of the park and other sections go around a portion of prairie area,” says Jamie Dowdall, site superintendent of Lake Le-Aqua-Na. “The terrain is variable. There are flat trail sections, hilly trail sections. We’re just on the edge of the unglaciated portion of the state, so it’s hilly out here as compared to a lot of parks.”

After being closed for nearly two years for renovations, Lake Le-Aqua-Na reopened Sept. 1. Now, visitors have newly paved, less-treacherous roadways. That’s particularly helpful for those who enjoy towing their campers up the winding hills.

There are 141 electrical campsites at Lake Le-Aqua-Na’s Hickory Hill Campground, plus 32 nonelectrical sites. There are also specific equestrian camp sites for those bringing their horses.

Unfortunately, the 40-acre lake remains closed until water levels are restored, which Dowdall expects to happen next spring.

“We’re kind of a rural park,” says Dowdall. “We’re out here in the country, off the beaten path, but people who come to the site really love it. Lots of people say this is their favorite park.”

To book a campsite, visit or call (866) 716-6550.

Freeport’s Wine and Witches Boo-tique Walk draws shoppers and diners to downtown’s many small businesses. It’s scheduled for Oct. 14 this year. (Swank and Mercier Photo)

5. October Shenanigans

If timeless activities like shopping, dining or recreation outside aren’t quite enough to get you to Freeport, there are numerous special events during October that may catch your attention.

Wine and Witches Boo-tique Walk

Oct. 14, 5-7:30 p.m., Downtown Freeport

This downtown shopping experience takes advantage of the Freeport Festival District, a special area where patrons can purchase adult beverages from downtown establishments on certain days and walk with open containers as they enjoy the area, says Haas.

At least 10 businesses will participate in the Boo-Tique walk, says Spachman, including boutiques, restaurants and bars that’ll host pop-up shops for smaller businesses or individuals who don’t have a brick-and-mortar building.

“You can dress up if you wish – wear your best witch costume or fun fall attire – or come as you are,” Spachman says. “Downtown businesses will provide a night of shopping, drink specials, treats, live music, store specials, giveaways and more. Every store does their own little thing. It’s such a great time.”

Puttin’ The Car Away – Car Show

Oct. 16, noon-2 p.m., Union Dairy, 126 E. Douglas St., Freeport

The last car show of the season takes place at Union Dairy. Music is provided by 3D Sound and Company.

Train of Terror

Oct. 16-30, Sat. 6-9 p.m., Silver Creek and Stephenson Railroad Depot, 2954 S. Walnut Road, Freeport

Those who dare to ride the Train of Terror are in for a scary treat. During the last three Saturdays of October, patrons are invited to hop aboard an antique diesel engine that runs along a 2-mile stretch of old rail line on the east side of Freeport.

“You and your family or group board the train and you go out 2 miles into the woods and pass all these vignettes,” says Haas. “It’s like a haunted house feel – things might jump out at you. It’s definitely in the spirit of Halloween.”

Members and friends of the Stephenson County Antique Engine Club have spent the past two decades preparing haunted scenes along the rail line, which starts at the Silver Creek and Stephenson Railroad Depot, says Mary Seefeldt, member of the engine club. It’s one of the biggest fundraisers of the year for the club, which aims to promote the education of old antique farming equipment, including its 1912 Heisler steam engine.

“There are lots of ghosts and goblins, witches – everybody creates what they want to,” Seefeldt says. “There are shadow scenes that people do, fractured fairy tales – where the big bad wolf is chasing Little Red Riding Hood – skeletons, guillotines, cemeteries … anybody can build a scene.”

In the past, the Train of Terror has given rides to 1,000 patrons in a single evening, Seefeldt says.

Train rides leave on the hour, every hour between 6 and 9 p.m. The cost is $8 a person; tickets are available at the depot, located on the northeast corner of W. Lamm and S. Walnut Roads. Learn more at

Trick-or-Treat Trail

Oct. 30, 3-5 p.m., Krape Park, 1799 S. Park Blvd., Freeport

The Freeport Park District hosts this annual event in Krape Park, where nearly 1,000 kids come donning costumes to grab goodies from community businesses and organizations.

“We ask organizations to set up a booth or display along the trails,” Schneider says. “We offer a trick-or-treat line that goes through the park. It’s a safe alternative to trick-or-treating in neighborhoods.”

The event is open to all ages. Masks are encouraged.

Are You Ready?

There’s much to see and enjoy in this small, but mighty community – and new things continue to pop up. Even locals are sometimes surprised at everything this renewed community has to offer.

“We’re definitely spread out, so unless someone asks or is directed to what attractions or things they can do in the area, it’s really easy to miss a number of the gems that we have in Stephenson County,” Haas says. “There are so many things to do, but you need to take the time to seek them out. You won’t be disappointed.”