An amazing Wisconsin destination any time of year is Sheboygan, located along the shores of Lake Michigan. Nicknamed the “Malibu of the Midwest” for its great winter surfing, Sheboygan is truly a year-round travel destination.
Sam and I enjoyed a lovely 3-day getaway to Sheboygan where we tasted the local cuisine, enjoyed the outdoor recreation, and relaxed to the sounds of Lake Michigan. Sheboygan surprised me in so many ways. The Sheboygan community is so tight-knit and connected. It has the cutest downtown with delicious restaurants and wonderful local shops. There are miles of beaches to enjoy year-round.
This post details a perfect 3-day itinerary to Sheboygan, no matter the weather (we had a lot of rain and still had the best time!).
Our stay in Sheboygan was graciously hosted by Visit Sheboygan, but all opinions are my own and I was not paid for this post. Sheboygan is truly a wonderful Wisconsin destination.
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Getaway to Sheboygan Itinerary:
Where to Stay
You’ll want to stay at the Blue Harbor Resort during your Sheboygan getaway. The resort is an excellent option whether you are traveling as a family, solo, or for a romantic weekend away.
The property is located along Lake Michigan and offers lake view rooms with a balcony that are perfect for relaxing and watching the water. Our room also had a large jetted tub that was perfect for soaking after a busy day exploring.
Another interesting tidbit about the Blue Harbor Resort – Sam remarked to our host that the hotel reminded him of Hotel Del in San Diego (where he’s from), and she responded that it was modeled after that property.
Day 1: Dinner, Drinks & a Lake Michigan Walk
Black Pig Restaurant
After arriving in Sheboygan and checking into your accommodations, head downtown to 8th Street for dinner at the delicious Black Pig Restaurant. Located across the street from the Stefanie H. Weill Center for Performing Arts, the restaurant offers an elevated dining experience in a casual environment.
If you feel like a post-dinner drink, visit On the Rocks Bar & Grill located within the Blue Harbor Resort. The bar offers classic and specialty cocktails, wine, beer, soft drinks, and a light fare menu. Enjoy your drink from the bar inside or grab a table on the outdoor porch while taking in the Lake Michigan views.
Walk off your dinner and drinks with a little stroll along the walking path next to Lake Michigan. The resort will light up the path and it makes for quite the romantic walk.
Day 2: Art, Shopping, and Relaxing
John Michael Kohler Arts Center & Art Preserve
Start your morning with a hot beverage and head to the John Michael Kohler Arts Center or Art Preserve. The Arts Center is located in downtown Sheboygan while the Art Preserve is located west of downtown near Bookworm Gardens and the UW-Green Bay, Sheboygan campus. Both are operated by the Kohler Foundation and are free to enter.
The Arts Center features beautiful grounds, several incredible exhibits, a workspace for artists in residence, and a project room. The Center also has the most incredible bathrooms. Each bathroom is uniquely decorated and even kids will enjoy checking them out and spotting the different themes.
Even if you only have a few minutes, you’ll want to make sure to get a walk through the Arts Center. I’m not typically a huge fan of art museums, but this one is really unique and non-traditional.
The Kohler Art Preserve is located in a separate area of Sheboygan from the Arts Center, but is equally impressive. The Preserve consists of three stories with over 37,000 square feet of exhibit space, and is situated next to property that is owned and protected by Glacial Lakes Conservancy.
You can visit both buildings Tuesday, Wednesday and Friday from 10am until 5pm, Thursday from 10am until 8pm, and Saturday and Sunday from 10am until 4pm. The buildings are closed on major holidays.
Browse the Local Downtown Shops
Downtown Sheboygan is home to numerous local shops that will give you a true taste of the city’s charm. The shops are locally-owned and each one has a unique story. I loved chatting with the storeowners themselves and hearing more about their businesses, as well as their Sheboygan recommendations.
Make sure to add these shops to your Sheboygan shopping day list:
- – WordHaven BookHouse, LLC
- – Olivu 426
- – Freaktoyz
- – Victorian Chocolate Shop
Relax by the Water or Poolside
After a morning of browsing the art galleries and shopping, grab lunch downtown and then spend the afternoon relaxing by the water. If you’re looking for a spot for lunch, Sheboygan has several delicious restaurant options – check out this post for ideas.
If you stay at Blue Harbor Resort you’ll have access to the beachfront, outdoor pool, and water park. Note that the outdoor pool is seasonal and the water park hours vary.
Even if you’re staying elsewhere in Sheboygan, the area has plenty of public beaches for you to enjoy the water.
Day 3: Breakfast, Sand Dunes, and Wine
Eb Flo Coffeehouse
Located across the street from the Blue Harbor Resort, Eb Flo is a riverfront coffee shop known for its croffles – a mix between a croissant and a waffle. It’s the cutest space, complete with large windows that let in so much natural light.
The back of the shop faces the Sheboygan River and there is ample outdoor seating to enjoy your coffee and croffle when the weather is nice.
I tried the Nutella strawberry croffle and it was really good. It was the perfect size and was just the right sweetness. You can also order smoothies, breakfast sandwiches, and a daily assortment of baked goods.
Kohler-Andrae State Park
Kohler-Andrae is one of the more popular state parks in Wisconsin, and for good reason. The park is situated along Lake Michigan and has several miles of beach and hiking trails.
Camping in Kohler-Andrae State Park is also very popular. The park has a 137-unit Family Campground (52 with electrical hookups), a group campground, and an accessible cabin that fits six guests.
You can swim from the beach and it is a gorgeous stretch of sand. Keep in mind that water quality in the summer can vary and small fish often wash up on the beach. There is no lifeguard present.
SoLu Estate Winery
Wine, events, and dogs – need I say more? Located about 30 minutes outside of Sheboygan in Cascade, Wisconsin, SoLu Estate Winery is the perfect place to gather for a glass of wine and enjoy live music. This family-owned winery is named after the owner’s children, and they often have their well-behaved pups roaming outside.
Head inside the tasting room to learn more about their wines and sample their offerings. The space is beautiful and the staff is very knowledgeable about the grapes and wines. It would be such a fun place to go to for a date or a girls’ night out.
The grounds of the winery are gorgeous and I highly recommend sitting outside when the weather is nice. Frequent live music events are hosted on the estate and you can reserve a table on their website.
I visited during one of their weekend events and was able to enjoy live music while sipping wine and grabbing snacks from the food carts on the property.
Conclusion
With its cozy size, lakefront location, and array of offerings, Sheboygan is truly ideal for your next weekend getaway.
