Plenty of family fun in Sheboygan, Wisconsin. Find a great art museum, murals, quirky roadside attractions, a whimsical garden, and beaches!

If you’re looking for a quiet destination, look no further than Sheboygan, Wisconsin. I believe it’s such a hidden gem! Art lovers can soak in the outdoor murals, quirky roadside art attractions, as well as a wonderful art museum. Find a whimsical garden and so much more! Plus, you can’t beat Sheboygan’s location right next to Lake Michigan. Plenty of beach here, folks! 

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Top things to do with the family in Sheboygan

Visit a whimsical garden

Since we are American Horticultural Members, we used our reciprocal membership to visit Bookworm Gardens. A visit to these whimsical gardens is a must for book or garden lovers! (Check out this list of all the books recreated.) In the past I remember the staff fondly talking about their Halloween event.  So when we had the chance visit to visit during Halloween, we jumped on the opportunity. Despite COVID, the Halloween event was simply magical and a Halloween to remember.

For all things Sheboygan

Our hotel (see below) was across the street from the new Sheboygan Visitor Center so we stopped by. They have wonderful Sheboygan souvenirs should you be interested. We also popped by to see the rotating Earth. Pretty neat!

Above and Beyond Children’s Museum

I visited this museum on our past visit and it’s so much fun for the kids. Unfortunately, during our visit it was closed due to the pandemic. BUT, I still urge you to visit. There is a fun music garden AND my absolute favorite mural located on the side of the building.

Walk downtown

Downtown Sheboygan is quiet with a few shops you can visit. I like walking down and checking out the window art and of course this Sheboygan sign.

See a shipwreck

If you’re fascinated by shipwrecks (the Door County Maritime Museum is a MUST!) like I am, then you must make a stop at Deland Park where you’ll find the remains of the schooner Lottie Cooper. So cool!

Beach time

It may have been windy and frigid but we never pass a chance to go to the beach when we can. So off we went to explore North Beach at Deland Park. What a breathtaking beach! I can imagine what a hot spot this would be during the summer. But on our particular visit, we had the beach to ourselves.

I’ve heard Sheboygan is the “Malibu of the Midwest” and could absolutely believe it when we saw those crazy waves. As a matter of fact, we saw one person surfing. In November. In 38 degree weather!   Make sure to stop and check out the colorful beach house. I love it!

We gave the kids a few minutes to run around on the playground.

Get your art fix

John Michael Kohler Arts Center is a wonderful art museum. And you must check out the bathrooms. It is definitely a work of art. Each bathroom is unique so try to check all of them out. During the pandemic, you could have the entire bathroom to yourselves. (They only allow one family at a time.)

Make sure to see check out the outdoors. The stone gardens, The Garden of Carl Peterson, is so interesting and worth a browse.

Tip: Stop by the arts center where you can take home activities (all for free!) The activities reinforce some of the concepts seen when you stroll the museum

I Spy Concrete Sculptures

I love quirky finds and visiting the James Tellen Woodland Sculpture Garden was right up our alley. (We’re huge fans of the John Michael Kohler Arts Center and saw this was managed by them.) Located just south of Sheboygan in the town of Wilson lies concrete sculptures created by James Tellen. We followed the path covered by yellow leaves and found sculptures in the tall woods. The sculptor couldn’t have picked a better setting, and fall visit was just so perfect. The leaves were at its peak and a family of deer decided to grace us with their presence. We saw there was a trail too. Next time!

Where to eat

Arrosto Deli

A New York style deli in Sheboygan, Wisconsin? Well, how could we NOT try Arrosto Deli? Choose to make your own sandwich or stick with one of their suggestions. The paninis are HUGE. My kids could have easily shared one. Online ordering was a breeze.

Recommended: The Evan had so much flavor!

Greece E Spoon

Greek food taken up a notch. We ate here a few years ago and was so glad to see that they were still around. So yummy!

Recommended: Greek fries, Chicken sandwich with saganaki, basically anything with saganaki

*Tip: We took our food to go and enjoyed it at a parking lot by overlooking Lake Michigan. The waves were pretty fierce and quite a sight to see.


Where to Stay

Harbor Winds Hotel Sheboygan

The two-story inn is simple but everything we needed in an overnight stay. Free hot breakfast (to-go during Covid times) and the BEST location right on the Riverwalk. We stayed here a few years ago and came back again because of the fantastic.  Being runners, my husband and I looked forward to our morning runs right along the river. We also recently found that the path can be taken to Deland Park and the beach! Now even more reason to visit.

Blue Harbor Resort

If you truly want to make it a getaway, a stay at Blue Harbor Resort is so fun! Themed rooms, a wonderful location by the beach, and a waterpark make this a hit with families.Read more about it here.