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A First-Timer’s Guide to 48 Hours in Sheboygan


A First-Timer’s Guide to 48 Hours in Sheboygan

Hello and Happy Friday, Readers! I’m back with another blog, and this week marks the fourth full week I have been in Sheboygan. Which means (at least I hope it means) that after nearly a month of being here, I can successfully write a blog on must do’s in Sheboygan for those who are visiting for the first time and are only here for a limited amount of time. Maybe my blog has peaked your interest in learning more about this quaint little beach town nestled halfway between Green Bay and Milwaukee. But what is there to do in this town? What makes Sheboygan so special, and how would you spend your time here? Buckle up, because I’m about to spill my whole 48 hours in the Malibu of the Midwest itinerary with you (and trust me, I intend to make sure there is a little something for everybody). Without further ado, we’re going to start with your first hour in Sheboygan:

Friday, 4:00 PM

You arrive at your destination after a day of travel. The sights of the town, the colorful houses, the sandy beaches, the streets of downtown, the smells coming from the restaurants, and the fun shops and surf-culture influence are all grabbing your attention. Where do you even begin? I suggest making your way down to the Riverfront Boardwalk. Depending on the weather, dress comfortably enough that you can enjoy strolling alongside the water looking at the different boats passing by and the businesses that line the Boardwalk, but also in clothes that you would be okay stopping for dinner in.

It’s 5o’clock somewhere…oops I mean, 5:00 PM

I understand not everyone is a drinker, nor is everyone 21 years old and up. But I have a cool destination to share with people of all ages and tastes: Bar 43. Located along the Riverfront Boardwalk in front of the Marina, Bar 43 is a cool lookout tower mixed with a sleek bar and views you just can’t beat. You’re welcome to order a cocktail or seltzer of course, but if you’d rather settle for a soda or lemonade, you can take whatever beverage you choose out onto the deck of the lookout town and gaze at Lake Michigan. Talk about starting your evening right, it feels like cloud nine sitting on the highest levels and seeing nothing but white boats and the bluest water stretching beyond the horizon as if it were the ocean. In fact, I have a hard time reconciling that I am in Wisconsin still when I sit up there enjoying the breathtaking view. And good news for those who might be visiting during a chillier time of year, there are fire pits built into some of the tabletops out on the balcony and an array of indoor seating that still allow you to soak up the view of the marina. Once you’re done with your drink at Bar 43, you may be interested in looking for dinner somewhere. Good thing you’re along the boardwalk…

6:00 PM

Both the North and South side of the boardwalk are plentiful in food and beverage options. Take some time enjoying the view while you decide. Parker Johns BBQ is a popular destination along the riverfront. Although it’s not on my 48-hour itinerary due to my many dietary restrictions, it is a favorite among the locals for its popular ribs, wings, fish, and sandwiches. Pacifico Mexican Bar and Grill has gluten-free, vegetarian, and pescatarian options, including an avocado salad that is calling my name. I’ll always choose anything that includes avocado in the title. That or hummus, but I digress. Starting off your 48 hours in Sheboygan at the Boardwalk is starting off right, because you’re in a prime location to really take in your surroundings.

7:00 PM

If you feel like heading to a new place for a dessert, not only are you surrounded by ice cream options such as South Pier Parlor and Blast Soft Serve, but there are some pretty cool smoothies and dairy free choices as well. South Pier Parlor is a popular destination if you’re looking for Sundaes, a large selection of scooped ice cream in a cone, or ice cream and soda concoctions. Blast Soft Serve is, as you might guess, best known for their variety of soft serve ice creams, in addition to their popular Flavor Bursts, Flurries, Dole Whip, Floats, Frosties, and Shakes. My favorite thing about these two businesses is that they offer such a wide array of desserts, including dairy free sorbets and dole whips. My go-to order at Blast Soft Serve is the Cherry diary-free Dole Whip with chocolate chips sprinkled on top. I am a firm believer in dessert between dinner and bedtime, I like to imagine it ensures sweet dreams (pun intendedJ). Of course you can always head back to the resort for a scoop of our locally-produced Cedar Crest Ice Cream right in Shoreline Café.

9:00 AM

 Now you might be wondering to yourself, did Em say something about surf culture in Sheboygan at the start of this blog? You are remembering correctly! An influential reason why Sheboygan is so commonly referred to as the Malibu of the Midwest is because the surfing culture here is insane. Lake Michigan may not be the ocean, but it’s fresh water and shark-free waves are just as strong and powerful as the ocean. Lake Michigan is a force to be reckoned with, it requires the same amount of respect and caution, but with proper preparation, you will feel like you’re on the coast of the Atlantic or Pacific Ocean. So for these reasons, you absolutely must either visit one of the beaches here in Sheboygan, or if the weather doesn’t cooperate for a beach day, checking out surf and beach culture businesses like the Weather Center Café or EOS Surf Shop. What better way to start your day than with coffee and the beach? The two local shops are a short walk from each other in the downtown area. The Weather Center Café is along the north side of the Riverfront Boardwalk and has a menu full of breakfast and lunch options like coffee drinks, non-coffee drinks, sandwiches, bakery treats, quiches, and more. Plus, they include gluten-friendly and non-dairy choices. If you can, I enjoy sitting outdoors with my go-to order of a lavender latte with Weather Center’s homemade granola, and enjoy the view of the boats driving in and out of Lake Michigan via the Sheboygan river. EOS Surf Shop is a short walk up the hill from Weather Center and is in the heart of downtown businesses. They carry plenty of surf, skate, and other outdoor activity gear, but also have a unique selection of Sheboygan related clothing, stickers, and hats. It’s a neat little shop that I recommend everyone check out, whether you are interested in outdoor sports or not. There is a touch of Sheboygan in most of their products, plus, the surf and skateboards propped and mounted along the walls is a must-see. When you’ve had your fill of the surf scene, you’ll be surrounded by other shops to check out.

12:00 PM

You’re probably getting hungry right around now after your exploration of downtown Sheboygan and it’s unique and colorful surf culture. Since you’re already in downtown, you absolutely need to check out Field to Fork for lunch. They are located just across the street from EOS Surf, and conveniently the Victorian Chocolate Shoppe is just a few doors down when you’ve finished lunch. Field to Fork has been shortening the distance your food has to travel from where it’s grown to where it ends up on your plate for nearly 20 years now. It’s a cozy and rustic café that is open for breakfast and lunch as late as 3:00 pm. The food is delicious and, as their name suggests, entirely fresh. They keep in mind special dietary needs at Field to Fork, so this is another great dining experience for anyone who has any special requests or concerns. Field to Fork also has a market called Slo Food Market. The best way to describe it is like a small, locally owned Whole Foods. You can do your grocery shopping there, but you can also pick up a coffee and bakery item, or sit down and order a soup or sandwich for lunch. All of the food in the market is organic, locally grown and produced. They share the same food philosophy as Field to Fork, and are all about ethically sourced food products that are clean, healthy, and fresh. I can’t pass up the opportunity to check out the market and not bring home a snack for later or treat for the next day.

1:00 PM

For the afternoon, you’ll want to make your way to the John Michael Kohler Arts Center. This art center has something for everyone, may that be an appreciation for fine arts, a sense of exploration and adventure, an interest in the odd and unusual, even an interest in seeing some pretty unique bathrooms. And trust me when I say you can kill plenty of time exploring these rich and interactive art exhibits. There is historic as well as contemporary art to be seen, considered, and appreciated—this attraction can truly be enjoyed by people of all ages. Better yet, if you are an artist of any medium, whether that be paint, sculpture, photography, multimedia, the list goes on, the Art Center is a space that was designed to be an artist-environment. This means the building was designed in a unique form that can be transformed by an artist to embody, express, and inspire artists work. Who knows, you might not consider yourself an artist, but I believe everyone is and can be. Visiting a creative space like this one might just help you come to the same conclusion.  If you do want to try your hand at your own artistic pursuit, JMKAC has a hands-on creative space for people of all ages to engage with their imagination through artistic skills. Whether you’re looking for something entertaining for the kids to do, or you want to test your own creative capabilities (maybe alongside a friend, partner, or family member) it’s fun to utilize this space for experimentation.

4:00 PM

Hopefully you enjoyed JMKAC to the fullest and are wrapping up your day of sightseeing around 4 o’clock. Now might be the time for that bakery treat you saved for later from Slo Food Market. Since today is all about exploring the many things Downtown Sheboygan has to offer, you should stroll around the streets and take notice of all the dining and entertainment. Dinner and show? Sheboygan can do that. Maybe a drink at Harbor Lights bar. This coastal bar and grill serves the one and only, 3 Sheeps Brewing Company beer, and overlooks the river and Lake Michigan in a neat historic building complete with indoor and outdoor seating in a fenced-in backyard. This is a bar you can enjoy year round, and is a Sheboygan favorite. Their Bloody Mary’s with grilled cheese are quite impressive to see, and much more impressive to enjoy. But don’t fill up too much, you’re going to the Black Pig for dinner next.

5:30 PM

The Black Pig is on N 8th Street near the Mead Public library and the JMKAC. It also happens to be straight across from the Weill Center for the Performing Arts. If you have tickets for a show there, the Black Pig is a popular destination to sit down for dinner before heading in to take your seats. The interior is cozy and atmospheric. The Black Pig is best known for its casual comfort food with a twist, by adding their own touch to popular comfort meals and drinks. Their list of specialty drinks is like no other, it has classics like Old Fashioneds and Bloody Marys, but they also have cocktails like the Rupunzel which has flavors of Chrysanthemum, honey liquor, and Moscato. The array of food options on their menu is similar, including dishes like truffle Mac as well as BBQ pork Mac. One thing is for certain, you won’t leave this restaurant hungry!

7:00 PM

Alright, what are you going to do before you call it a night? Maybe you’re interested in an activity such as an escape room, or axe throwing. Maybe you’re more the entertainment type and you are going to simply cross the street to the Weill Center for a show. Maybe you’re a night life person and you’re going to stick around at the unique bar in the Black Pig and taste test more of their incredible cocktails. Or perhaps the weather is just right for an evening walk to the beachside Deland Park. Or, you may simply want to retire for the night and enjoy some rest and relaxation. If none of these options suite your desires, click here to see a full list of Sheboygan events that might inspire you to make this 48-hour trip. You’ve had a full day of fitting in Em’s suggestions for exploring this beach town. But don’t be fooled by this reminder of your free will, you still have one more fully day in Sheboygan, and this blogger is far from running out of ideas to fill your 48 hours in Sheboygan.

9:00 AM

Rise and shine! You have less than 24-hours left in Sheboygan, and there is much yet to see and do! To start off your second day, head to Café Bella for breakfast. Their wide selection of breakfast foods ensures that there is something for everyone whether you like a sweet or savory breakfast, big or small, with coffee or juice. Café Bella is located across the street from South Pier drive and is conveniently close to Blue Harbor Resort if you are staying there.

10:00 AM

After breakfast, pack your lunch in a beach bag, along with a swim suit and sunscreen if it’s warm, or your winter coat and boots if it’s cold, because rain or shine you must visit Kohler Andre State Park. These hiking trails go up and down sandy dunes, rope railings, and beach grass that will transport you to a place that certainly doesn’t look anything like the Midwest landscape you imagine in your head. Kohler-Andre is a beautiful park for a beach picnic, a hike in the cooler months, or a swim during the summer. It’s also a prime location for taking photos. If you’ve been searching for the perfect nature location to take photos with your romantic partner, family photos, or Christmas cards you’ve found it. The sand dunes are swooping and majestic, the water shimmering and endless, and the beach is light and fine grained. Kohler Andre is a kid and pet-friendly place to visit with your family. There are parts of the park that are not pet-friendly, but the hiking trails, marsh boardwalk and trail, and beach are. As long as you are being aware of the signage, you can have a pet-friendly family escape into nature that will sustain you for a whole days’ worth of adventure. As you walk by the beach, keep a lookout for the ten-shaped forts of driftwood that are scattered throughout the beach by people building beachside forts to play in or to simply enjoy a playful process of creative building. Stop by the nature center during your visit to the park and learn more about the native wildlife, and pick up hands-on booklets filled with educational activities that could keep you busy for days. Additionally, the nature center is home to the gift shop where you can find nature and state park souvenirs.

3:00 PM

After a long day exploring the outdoors, your 48 hours in Sheboygan are nearly up. It’s time to get one last taste of the town before hitting the road. Pizza sounds pretty good after all that hiking and adventuring, so make your way to Faye’s Pizza. Faye’s has been a Sheboygan favorite since 1957, they make their handmade pizzas the traditional way, using fresh ingredients, including their dough, created fresh every day. The thin crust pizza they are known for can also be made gluten-free upon request.

Congrats, you’ve just completed the itinerary!

48 Hours in this beautiful and quaint beach town only skims the surface of what Sheboygan has to offer (pun intended). I hope that 48 hours is all one needs in order to whet your appetite for another visit to continue exploring all the experiences to be enjoyed here. After my first four weeks of living in Sheboygan, I am so happy to be here and it feels more and more like home each day. I keep finding and loving something new in this town the more time passes, and I can’t wait to continue updating this blog with my discoveries. Until next week, rock on, Sheboygan.

48 Hours In Sheboygan Itinerary At A Glance


4:00 p.m. Walk around the Riverfront Boardwalk

5:00 p.m. Happy Hour at Bar 43

6:00 p.m. Dinner along the Sheboygan river

7:00 p.m. Ice Cream Dessert at South Pier Parlor, Blast Soft Serve, or Shoreline Café

Day 1

9:00 a.m. Breakfast and coffee at Weather Center Café, and check out EOS Surf Shop

12:00 a.m. Field to Fork lunch and Victorian Chocolate Shoppe for dessert

1:00 p.m. JMKAC visit

4:00 p.m. Swing by Slo Foods Market

5:30 p.m. Sit down for a drink at Harbor Lights Bar and Grill

7:00 p.m. Dinner at the Black Pig

Day 2

9:00 a.m. Breakfast at Café Bella

10:00 a.m. Kohler Andre State Park Day! Hiking, beaches, swimming, photos, nature center, etc.

3:00 p.m. Faye’s Pizza to refuel after your successful Sheboygan visit!


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