Just one hour away from my home in Green Bay is the city of Sheboygan. Yet before this October, I had never really been to the area before. Sure, I had driven through and seen the World’s Largest Symbol of Freedom from the road, but I hadn’t explored the other things that Sheboygan had to offer. I am happy I spent a weekend in the area to experience the city. Now, I have some new favorite restaurants and shops in the area, as well as a list of things I need to try when I visit again. Curious what you can do in the Malibu of the Midwest? Read on for my 2-day trip adventure!

On a Friday night, after work, I drove to Sheboygan. It was a quick and relaxing cruise! I arrived around 6:00 pm at The Watershed Hotel. I was very impressed with the overall aesthetic of the place. The lobby’s big fireplace gave all of the coziest vibes. My room was very modern and chic with a balcony overlooking the Sheboygan River. I got settled in quickly and ready for my dinner reservation.

I’m glad I went hungry to BoMallies because there were so many great dishes to taste. First up, I enjoyed some Beef Khalbi Smashed Dumplings. Then, I had some of the special of the night: Seafood Ravioli. I couldn’t resist the Mozzarella-Stuffed Meatballs (I’m a big fan of vodka sauce). And finally, I tried the Banh Mi Tacos. Everything I ate was absolutely incredible.

I highly recommend visiting this place with a friend or a group so you can sample around the different plates! I think the Smashed Dumplings may have been my favorite, but the Banh Mi Tacos were a very close second.

To drink, I had the Wisconsin Mule. It had cranberry vodka with honey, orange and rosemary syrup, fresh cranberries, and lime. Tasty and on the sweeter side! But, I suppose that wasn’t the only sweet thing I enjoyed… After a delicious meal, I had to try the Car Bomb Cake. Guinness chocolate cake, soaked with Baileys, Jameson cream cheese frosting… anyone else drooling?

Not only did BoMallies impress me with food, but also art! The walls were covered with unique pieces, and I even spotted one of my favorite artist’s works, Donald Topp. Yes, those are the ladies of the Mystery Machine all tatted up; I adore them.

Post-dinner, I wanted to check out 3 Sheeps Brewing. I always enjoy exploring breweries outside my area and adding new brews to my Untappd profile! At 3 Sheeps I enjoyed a Pumpkin Spice Beer (’tis the season). Typically, I don’t go for dark beers, but this one was nice and smooth. 3 Sheeps’ indoor space was roomy and definitely felt like the place to be on a Friday night.

The next day, I woke up to a gorgeous view from my hotel room and began getting ready for more exploring. My first stop was the Sheboygan Visitor Center. Here, you can get all of the information on local things to do, shop for souvenirs, and find unique pieces from local artists. They had a pull-tab art kit that I thought was awesome (here’s the artist’s site).

To fuel up, I visited Eb Flo Coffeehouse for a latte and avocado toast. The aesthetic was very relaxing, and I loved looking out on the water while sipping my coffee. This place made for a satisfying breakfast and a great start to the day.

I knew when I was planning to visit Sheboygan that I wanted to check out some local shops. First up, I visited the Hello Happiness Creativity Center. It’s a craft supply store that has new and second-hand items to get creative with. I enjoy bullet journaling and collaging, so I was excited to find bundles of different papers to work with. Whatever your craft of choice may be, I believe you’ll be able to find something that inspires you at Hello Happiness.

In Downtown Sheboygan, there were lots of shops to look around. Nikki’s Nex2New consignment shop was right up my alley. There, I found a cozy cardigan and a cute top to take home. Mainstream Boutique was fun to look around. They had lots of pretty pieces and perfect styles for the current fall and winter seasons. If you’re looking for a classic thrift shop, Revolution Resale is a great place to go.

One of my favorite shops was FreakToyz. They sell all sorts of unique toys, figurines, comics, and collectibles. I saw everything from Teenage Mutant Ninja Turtles to Doctor Who to Harley Quinn to… the list goes on! This place really had so many amazing things to look at. Here, I picked up a little Ash Pop Figurine to add to my haul.

In between shops, I discovered some murals downtown. The street art in Sheboygan is very lively and energetic. If you visit, don’t miss your chance to get abducted in the UFO mural!

I also explored the John Michael Kohler Arts Center (JMKAC). It’s an art gallery that’s free to enter and look around! They also offer other programs and activities to engage with the arts. I was happy my visit landed at the same time that Patricia Piccinini’s exhibit, Encounters of Another Plot, was on. It was incredible to see it in person. I also caught Bea Fremderman’s exhibit, Weeds Compared to Flowers, which was very interesting (you can catch it until February 18, 2024). Also, did I mention that the JMKAC washrooms are works of art too?!

Walking around shops and art helped me work up an appetite for lunch. Pizza sounded good, so I ended up at Il Ritrovo. Little did I know that this pizza would definitely ruin some other pizzas for me. Il Ritrovo was the 5th Certified Vera Pizza Napoletana member in the United States. So what does that mean? Their wood-fired, Neapolitan pizza is authentic. Special training and strict requirements are needed to be a certified established. In short, this place is the real deal. It may go without saying, but the pizza was delicious!

Before hitting the road home, I had to take a moment to look out at the water and see if I could catch any surfers riding the waves. In case you didn’t already know, Sheboygan is nicknamed the Malibu of the Midwest because of its surf community! Yes, people surf on the Great Lakes (even in the winter).

I had the best time exploring Sheboygan for a couple of days and getting to know the area. Huge thanks to Visit Sheboygan for hosting me and guiding me on the adventure.

Have you been to Sheboygan? What local spots do you love? I would love to hear your thoughts in the comments or on Instagram. Let’s chat!