When Wisconsin residents hear the city name Waupun, some might admit that the likeness of a prison is what comes to mind.
Nicknamed “Prison City,” with three prisons in the city itself, and one of them being the oldest in the state, it would be easy to understand why.
But if you look past the images that those buildings conjure—concrete walls and metal bars—you will discover the unexpected: a second nickname for the city in the shape of a visual art form.
From metal to bronze, as you stroll through Waupun’s downtown, or “Sculpture City,” the city’s other nickname, you will be greeted by sculptures like “The World’s Her Canvas” by artist Lee Leuning.
Right on the sidewalk as if happening as you pass by, the sculpture depicts a determined young girl with a paintbrush in hand ready to change the world with whatever masterpiece she decides will illuminate the canvas. With an empty space where the canvas would be, the viewer is left to decide this for themselves along with the subject of the piece.
And while there has been a prison in Waupun since 1851, the nickname “Sculpture City” didn’t come too long after that. The legacy began in 1861 when Waupun industrialist and entrepreneur Clarence Shaler was born.
Shaler (1861-1941), also an inventor and creator, left behind a collection of bronze sculptures including the story of his own heritage, which he began sculpting at age 70. After his passing, the pieces were gifted to the city and now invite visitors from all over the world to view the collection. It’s one of the things that makes the city so unique, according to City of Waupun Mayor Rohn Bishop.
“Our city is naturally artful,” Bishop says. “With Waupun being ‘Sculpture City,’ we now have nine permanent sculptures and several rotating sculptures throughout our city, including the world-famous End of the Trail.”
Beyond the sculptures that tell a story, there is also a creative story behind the name Waupun.
“Waupun is a misspelling,” Bishop explains. “We were supposed to be Waubun (an Ojibwe word which means ‘dawn of day’). The spelling stuck, except for the error which changed the b to a p in 1840 when the city name was commissioned.”
Misspelling aside, Bishop says he loves how the people in the city work together, not just businesses supporting each other but the camaraderie the residents seem to share, even in stormy weather – literally.
“After a tornado or a flood, neighbors really come together and help each other,” said Bishop. “No one looted, and when the power was out, neighbors would hang out and drink beer while waiting for the power to return.”
And there seems to be something electrifying happening downtown with everything coming together to make the area a hot spot for both dining and retail destinations, said Bishop.
“Our entire downtown is really can’t miss right now! Fun bars, good restaurants, and lots of new shops,” said Bishop.
DINING TO-DO LIST
Speaking of downtown Waupun, if you walk down Main Street, you will find a place that beckons you in with the smell of coffee along with pieces of the city’s history which adorn the walls. But if it’s past java drinking time, don’t worry.
Breakfast
From beans to grapes, Wind and Unwined offers something for your morning wake up call to something you can purchase for a relaxing night cap.
Wind and Unwined is co-owned by Jeff & Lisa Collien and Brooke & Derrick Straks. The name materialized over dinner.
“She (Lisa) always wanted a little coffee shop. We had just got back from Colorado and they had a place that had wine and a coffee shop, which was unheard of at the time.” Collien says. “So we were having dinner on our anniversary and my wife was like, ‘What do you think?’ And I said, I would probably only do it if we did it with wine (I wasn’t sure coffee would make it on its own). Then she came up with the name. We wrote it on a napkin in 2014 and we didn’t decide to do this until 2018.”
Once they were able to find the space, which needed a lot of renovating—something Collien admitted he loves doing—it didn’t take long for everything to fall into place.
“I told her, if we’re going to do it, we can’t just have a normal coffee shop. We have to go after what we enjoy,” Collien remembers. “We’re pickers, and I’m a history freak. Almost everything in here has been repurposed.”
He notes the 12-foot tall door that leans up against a back wall came from a neighboring business, Chic Tique. But he said the door itself was part of a set that opened to a big ballroom in the 1920s.
“I found that (door) buried,” Collien says. “I also found a grocery sign that used to be in the store next door from the 1940s… There is something in here from almost every building or business (in downtown Waupun) that I tried to tie in.”
With meaning behind each item on the wall, he likes the idea of the interior of the business also being of visual interest, which goes well with the city’s second theme of “Sculpture City.”
“It gives you something to look at… You can sit down the next time (you’re here) and say, ‘Woah, I didn’t see that (last time),” he says.
Being a history buff, Collien is always interested in what Waupun has to offer residents and visitors alike.
“Waupun has a lot of history. There is no doubt,” he says. “But we have grown so much that we have a lot of people coming from out of town to shop because we have so many different boutiques.”
Beyond the uniqueness of downtown, the city has something to offer for everyone.
“We have a beautiful town. It’s the seventh safest city in the state. Every park has a river going through it,” Colien notes. “We have the marsh, bike trails. It’s really becoming one of those destination spots.”
Besides what he finds unique about Waupun, he said Wind and Unwined has its own little niche which brings people back.
With a variety of teas, espresso and specialty coffee drinks like their Saronno Sunrise Latte—espresso and steamed milk with a creamy frothy layer of steamed milk, with vanilla, amaretto and cinnamon—and Campfire Cold Brew: mocha cold brew topped with marshmallow cold foam and mini marshmallows and graham cracker—it’s no wonder guests become repeat customers.
If you’re in the mood for something hearty to start your day in Waupun, breakfast items range from Acai Bowls and Breakfast Sandwiches to Bagels and Yogurt Parfaits.
“We have customers from Milwaukee and Oconomowoc who come each week and drink wine here and say that there is just no other place they know of that they can sit (and unwind) like this,” he says. “We get a lot of compliments on how people feel at home when they sit here.”
Lunch
From winding down to winding up for a road trip, another popular place to grab a cup of joe and have some good conversation in Waupun is the Wild Goose Cafe.
It may be a truck stop, but like its unique name, this restaurant offers interesting fare for all three meals as well as Friday Fish Fry options.
Go in early and check out what’s on the griddle from a Belgian Waffle to potato pancakes or an Interstate Omelette, which mimics a Western Omelette.
If you happen to stop in around lunch time craving a burger, try a Black n’ Blue Burger, which is on the spicy side, or the Mac Daddy Burger, which is topped with Mac n’ Cheese.
For those who have to go the distance, they offer Long-Haul Dinners like Chicken Pot Pie and Meatloaf.
Josie Dobbratz, a waitress and occasional hostess at the Wild Goose Cafe has worked there for roughly four years.
“I like that it’s a small town,” she says. We have a lot of unique stuff that goes on here.”
She said the thing she likes best about the small town atmosphere in Waupun is the relationships she builds with her customers.
“We value the people that we have here. I can’t tell you how many close relationships that we build here. For example, these (customers) are our two o’clock people. They come in every day at two o’clock and eat,” Dobbratz says.
Dobbratz grew up near Waupun and says even though it’s small, she is able to meet people from all over Wisconsin and other states who visit.
“I love being able to talk with people from all over. I was in the military for a bit so I love talking to people who come from different cities and states… I’m really comfortable and love the people here.”
Besides working at the Wild Goose, she loves eating there too.
“Our food is phenomenal,” she says. “We’re always adding new specials. A lot of it is homemade.”
They also have a collaboration with a local meat market.
“We have the Eden Meat Market that’s attached to us so all of our meat comes from them,” Dobbratz says.
Based in Eden, which is about a half an hour from Waupun, the Eden Meat Market is another well-established business, having been in existence since the 1890s. In 2015, they celebrated 125 years of business.
Dinner
For Wisconsin supper club fans, Waupun does not disappoint with the Brittain Super Club.
Fans of Old Fashioneds and the traditional Fish Fry on Friday nights will find those there, along with favorites from the sea like Scallops. They also offer Prime Rib on Fridays and Saturdays and even a Sunday Brunch.
From Old Fashioneds to craft beers, what goes better with a thriving downtown scene than a brewery? The Hoya Hop House Brewery on Main Street is a welcome recent addition to downtown Waupun and brings with it food and drinks.
Run by Michelle Brown and her son Jarret Mack (Brewer) the family opened the brewery in January 2025.
Brown worked with Lauren Tilema, co-owner of Stone and Suede. When Tilema opened Stone and Suede she mentioned to Brown that the only thing Waupun needed was
a brewery, and that planted the seed.
With an effort to stay green, the brewery even offers a green space to sit and enjoy one of their handcrafted beers or unique signature cocktails like Bootstraps—brown butter fat washed larceny bourbon, Fee Brothers Turkish tobacco bitters, bittercube orange bitters and rich brown sugar syrup—or their Marge: Mijenta Blanco tequila, Ferrand Dry Curaçao, Lychee fruitful liqueur, lime juice, salt and heavy cream fat wash.
Favorite flatbreads include the Basil Blush—roasted garlic tomato sauce, fresh mozzarella slices, fresh roma tomato slices, fresh basil and balsamic drizzle and the Tuscan Harvest—roasted garlic tomato sauce, shredded mozzarella cheese, shredded garlic chicken, chopped artichokes, tomato confit and a pesto drizzle finish.
And if you don’t know where to go, or you just want a burger and a beer, there is always Our Bar or The Other Bar.
Our Bar, on Main Street, offers a casual dining experience and a place to chat and catch up with friends, either local or from out of town.
The Other Bar, also on Main, offers a wide selection of fish options for Friday Fish Fry, as well as traditional restaurant fare.
If you’re looking for a fun night out, try Jud-son’s Bowling in Waupun. Bring the family and order some fun snacks or pizza. With 16 lanes and automatic scorers, you can sit back and relax until it’s your turn to bowl. They also provide bowling balls with varied finger sizes and pool tables if bowling isn’t everyone’s thing.
If it’s pizza you’re looking for, try Tony’s Pizza. They take pride in their pies, so if you’re passionate about pizza, this is the place to try.
RETAIL THERAPY
From food to frocks, something amazing is happening in Waupun in terms of their retail scene. In a world of online shopping, Waupun’s downtown retail businesses aren’t just striving, they’re thriving!
If you ask Stone and Suede co-owner Janelle Kartechner why she thinks that might be, she says it’s the personal touch the business owners bring to the stores—most of which are owned and operated by family.
A sister team at Stone and Suede, Kartechner owns the store with her sister, Lauren Tillema. Owning a boutique had always been a dream of theirs, but they didn’t consider it seriously until they found themselves struggling with their chosen careers during COVID.
“We were actually both nurses. … it was during Covid time. We were working at the Beaver Dam hospital and had little kids, our husbands also owned businesses and we were very busy,” Kartechner recalls. “The job required more than we could give.
“We always had a passion for clothing and styling people. So, since we have that nurturing nature to us from nursing, we kind of said, ‘Well, I think we could do this. We could open up our own store.’”
Part of Kartechner’s drive, having lived both near and in Waupun most of her life, was also to bring quality clothing at an affordable price to the area as well.
“It’s such a great community and surrounding communities that we wanted to provide a one-stop shop where people can come and get affordable, good quality clothes and feel good about themselves,” she says.
Once they made the decision, Kartechner said it wasn’t long before she and her sister were branching out with their own boutique business.
“During COVID we talked it over with our husbands and they were like, ‘Take the leap, quit your jobs! They were so supportive,” she says.
The duo found the building they’re in now on Main Street in Waupun and, like Wind and Unwined, rehabbed the building.
“We found this building… It was two weeks away from a raise order. It was disgusting. It was moldy, had a hole in the ceiling, so we rehabbed it,” Kartechner says of the boutique they created.
“It’s our second home.”
They also strive to make visitors feel at home when shopping at Stone and Suede.
“I feel like we really have a passion for people and that we really care about how you feel. Not just how you look or about buying something but we want you to feel good and fulfilled and like it was worth coming,” Kartechner says.
To make it “worth the drive,” there are several other boutiques in Waupun’s downtown to allow visitors to make a day of it.
Kristen Schultz, owner of the Chic Tique, also dreamed of opening her own boutique. Her first brick and mortar was a bit less formal than the boutique she has now.
“Chic Tique started in my garage at home,” she says. “Then it moved to a granary on my home property. It started off with a painting/refurbishing business, grew into a store, and then right after COVID, I opened my first brick and mortar in Ripon. I’ve been there for four and a half years. Two years after that was open, we opened this location (in Waupun). So we’ve been here a little over two years.”
Originally from Waupun, Kartechner said she was grateful to get to go back home. The catchy name came out of one of Schultz’s first loves.
“I went back to my roots,” she says. “I actually started off more with antiques and that’s where ‘Chic Tique’ originated from. It was shabby chic, because I love shabby chic. And then, Tique came from antique. Now we just say the ‘Tique’ could be Boutique.”
The shop’s evolution from antique to boutique was really customer driven, with Schultz recognizing what was selling well in her stores.
“My true love is home decor, styling and interior design. However we started bringing clothing in and it’s been so receptive. It’s doing so well that we just keep adding,” she explains. “We try to hit every customer (with what we offer). I can have a group of ladies in here and there should be something for everybody.”
The design of the space intentionally allows customers to follow the flow based on what they’re looking for.
“What’s unique about Waupun is we have a diversity of stores. We have everything from clothing boutique at Stone and Suede, to Madeline’s, which has resale, also the Clothing Pallet. Then there’s Blue Heron, which is antiques and we have Gysbers Jewelry,” Schultz says. “I’m kind of the newer one with the home decor and mix of boutique.
“I just think that if you come to Waupun our stores are amazing. Each one has its own feel and look. It’s really just a great experience!”
After shopping on main street, your feet might need a little TLC. In that case, pop into Brooks Shoes & Repair. Much like the rest of the stores in downtown Waupun, the store has been family owned since it began.
“We bought it eight years ago this fall,” owner Gary DeJager says.
And while they didn’t get cold feet before they purchased the business, DeJager says they didn’t have an abundance of knowledge on the industry.
“We didn’t know a lot about shoes except wearing them,” he remembers. “We farmed for 25 years and then we got out of that. Then we did some other things. She was in finance so we had been our own bosses. We wanted to go back to that. When this opportunity came, we jumped on it.”
Even though they didn’t know a lot about shoes, they landed in a well-established business. Open since 1938, they also knew the previous owners, which fit well for what they were looking for in a business to purchase.
“It was very organized (the business). It was a turn-key,” Katie DeJager says. “And with my accounting background, I could understand that end of it.”
Gary DeJager supports the idea that what has Waupun’s downtown retail businesses thriving is the personal touch provided by the owners, most of whom are family.
“Well, we’re not chain stores. We’re all independent businesses,” he says. “The owners are there and we’re personable. We love to get to know our customers and what their needs are.”
Pulling out a rolodex of their customers, he said that it came with the store and they kept it because of the level of personal service it provides.
“We have a card on each of our customers when they come to get work boots. It’s old school, but customers love that,” DeJager’s sister-in-law, Gladys Montsma, who handles sales and promotions, says.
“People love that. We can see what sizes they’ve had and if styles have changed over the years.”
Brooks Shoes & Repair also takes pride in carrying on the tradition of an already established business in the area.
“When we bought the store, there were probably a handful of businesses in Waupun but we’ve been here for years. Gysbers (Jewelry) has been here for over 100 years… all the business owners are happy to talk to people and want to see you come back, so we want to offer you good service,” he says.
What’s old is new again at Bargain’s Galore Thrift Store. Gary DeJager sys some of the downtown businesses have actually shifted their hours around the thrift stores.
“They are open Thursday, Friday and Saturday, and they are so busy. People come from all over.”
“There are usually 80 or so people in line on Thursday morning,” Katie DeJager adds.
From retail to Reiki, there is something for everyone to do in Waupun. Tyra Lee Walters, proprietress of Reiki Essentials & Wellness, and Firefly Gift Shop says.
“Everything from places to eat, stay and camp; a swimming pool, nice golf course, a growing downtown historical district, easy access to the Horicon Marsh Wildlife Refuge, we are centrally located between Madison and the Oshkosh areas, and a nice variety of downtown shops,” she says.
Her store is unique in that it offers something other retail stores don’t.
“Many people know that we are the local rock shop, but also that we are ‘that spiritual place on the corner,’” she says. “People have come from as far north as Green Bay and from south of Madison to get here (to the store).”
She hopes to create a relaxed and calm atmosphere when people visit her store, which is something she said the downtown shop owners are also really good at.
“The downtown shop owners are really good at making the shop fronts ‘cozy’ and welcoming. We are all good at the art of hospitality,” Walters says.
At the end of your visit to Waupun, don’t forget to pick up some flowers for yourself or a friend at Ren’s Floral. Owned by long time employee, Heidi Braker, who purchased the business from Lisa Rens in 2018, her love of flowers shows in her exceptional design and care of her customers. The shop has been in Waupun since 1982.
After strolling through the sculpture garden, shopping at all of Waupun’s unique boutiques, grabbing some gnash and stopping to smell the flowers, why not head over to Charming Reads to pick up a good book for that summer read you won’t get to (at least you will have a book to bring to the beach and—who knows—you may read a page or two this summer!).
From children’s books to cozy mysteries, Charming Reads is exactly what the name implies: a charming book store that sells gently used books that look brand new but at a lower price.
CLEAR YOUR CALENDAR
“Celebrate Waupun is a classic small town festival. It is the last weekend in June and it’s a three-day family festival,” Erin Lund of Destination Lake Winnebago Region, the official Visitors Bureau for Fond du Lac and Waupun, says.
“We have headlining bands with this year’s headliners being Boogie and the Yo-Yoz on Friday and Vic Ferrari on Saturday. Sunday is Smartmouth. Imagine That! Art Studio in Waupun brings a tent for kids to splatter paint all around—they love that. There is also a carnival all three days and Fireworks on Sunday night.
Waupun Volkfest. In mid-September, Waupun celebrates “Volkfest,” a German Ethnic Festival. Kicking off Friday night often with Bingo followed by a band, the Kiwanis Pancake Breakfast and live entertainment run all day Saturday. The entire festival is filled with traditional German fare and craft beer.
If you’re visiting for the festival and need a place to stay, there is always the AmericInn and Baymont in Waupun with a lot of Bed and Breakfast options in neighboring towns.
