The Very Best Places to Go and Things to Do in Sheboygan Wisconsin

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The Very Best Places to Go and Things to Do in Sheboygan Wisconsin

Lucky me!  I was fortunate to spend several days in Sheboygan, Wisconsin.  This town lies on the shores of Lake Michigan and is only an hour south of Green Bay.  I loved exploring the beaches, eating in some unique restaurants, and learning about this great town.  It is impossible to sum up the whole visit in just one article, so in this article, we’ll focus on all the fun things to do in Sheboygan!

Shop Sheboygan

If you are fortunate enough to have more than one day in Sheboygan, you’ll want to explore the many options for shopping in Sheboygan.  You’ll find great places to eat, shop, and entertain the grandkids!  Let’s begin with some excellent places to shop in the downtown area around 8th Street.

WordHaven Bookhouse

Are you a reader?  I sure am!  The WordHaven Bookhouse is the perfect place to get lost in a story.  You will find this darling little bookshop at 923 N. 8th Street in downtown Sheboygan.

Be prepared.  Upon entering, the smell of paper and books will assault your senses.  It is a comforting smell, like the warm sniff of a baby’s fuzzy forehead.  Immediately I was drawn to the beautiful shades of purple and teal covering the walls.  This bookstore feels like home.

The Bookhouse’s centerpiece is a large table, perfect for meetings, classes, or workshops, which WordHaven hosts routinely.  Be sure to wander and take in the store in its entirety.  You may be as delighted as I was to find the darling little seating area for kiddos, complete with a Baby Yoda chair.  I wonder how many small children have had a smackdown over who gets the cool Yoda chair.

When you visit, I hope you meet the owner, Kelly, whose delightful and welcoming smile will make you feel right at home.  This little shop is a labor of love for all to feel loved and included.

The exterior of WordHaven Bookhouse - a brick building with large glass windows and a flowerpot near the door.
Even the outside of this bookshop is inviting.
Interior shot of the Wordhaven Bookhouse showing teal and purple walls and several shelves with books upon them.
The kid’s reading nook is right behind that section on the left.

Olivu 426

The first thing I noticed when I walked into Olivu 426 was the crisp, clean scents surrounding me and the bright, clean, and cheerful atmosphere.  Located at 502 North 8th Street, Olivu is as lovely as her owner, Caitlin Brotz.  With a bright, sunny smile, Caitlin told me the compelling story behind the founding of Olivu 426.  In short, this fun shop is devoted to creating personal care products that are natural, healing, and affordable. 

I took home some of their Ocean Kissed Hair Gel (sea salt spray) for my pink hair, which I prefer to wear messy and disheveled.  I have bought sea salt spray from many places and paid a lot of money for many fancy brands, and I am sincere in telling you that this is the best sea salt spray I have used.  I love it!  And my favorite part?  The smell!

Customers can choose from over 150 scents to add to their favorite skincare or hair care product.  So no more worrying about the perfect product with the less-than-perfect smell.  I have already ordered more for me, and now my son keeps swiping mine, so I’ll be picking some up in a much more manly fragrance for him.

A brick storefront on the corner with a green awning with the word "Olivu"
Olivu sits on a corner and is nice and bright inside thanks to the large windows.
Seven women laugh and smile inside Olive, with various olive oil-based products surrounding them.
We had a great time exploring Sheboygan and we really loved Olivu and the story behind it!

Hello Happiness Creativity Center

The Hello Happiness Creativity Center is a great place to spend free time letting out your inner artist!  This non-profit organization at 1504 New Jersey Ave has supplies, tools, demos, and products to inspire creativity!  Hello Happiness gears its in-studio workshops toward adults and teens.

The Shop Happy area is a thrift store that gives new life to pre-owned art supplies and ridiculously inexpensive new items.  There is even an area with freebies, so no one leaves empty-handed.  Shop Happy takes donations, so if you’re clearing out your art supply at home, bring your goodies, and be assured they’ll find new life!

You can find a list of classes HERE, or stop in and say hello and see what this interesting shop is all about!

Six Turtles Boutique

Six Turtles Boutique is located at 833 Pennsylvania Ave, Ste 102, and is the first brick-and-mortar store owned by hubby and wife team Lauren and Mike.  They began selling women’s fashions online and were excited to open a shop in Sheboygan in 2021.  Now their customers can try before they buy!

My favorite part?  Six Turtles Boutique is size-inclusive and has many options, even for this fluffy size 2X Hip Grandma.  And when I had a last-minute change of schedule and needed to stay an extra night, a local friend immediately directed me to this darling shop to pick an outfit to stay stylish on my extra day in town.  The staff was friendly and accommodating, too! 

Finally, if you want to grab some Sheboygan Swag to wear home, this shop is for you!  You can even buy it online.  Thanks, Six Turtles!

Shop Along the Riverfront Boardwalk

The Riverfront Boardwalk is on the South side of the Sheboygan River and is a lovely way to spend a little time checking out the shops and taking a stroll along the boardwalk.  This beautiful area offers multiple places to relax and watch the boats cruising through the harbor.  Grab breakfast or a snack at the Weather Center Café, then peek at some cool shops.  Here is a couple that I loved!

A bright blue sky with scattered white fluffy clouds and a couple of  boat docks in the forefront.
The sky was gorgeous and the air was chilly when I visited.
An orange leaf sticks up from between boards on the Riverfront Boardwalk.
I couldn’t resist this beautiful image of a leaf sticking up from between boards on the boardwalk. Wondering how to get a pic like this with a blurry background? Check out What Do I Need to Know About Depth of Field?


Olivada is the only place in Sheboygan to enjoy free samples of over 45 fresh extra virgin olive oils and balsamic vinegar flavors.  Look around and find free recipe cards to help you liven up your home cooking!  I picked up a delicious mix-in for my olive oil that works perfectly for dipping bread. You will find Olivada at 641 Riverfront Drive.

a shiny cement floor with a long table filled with bottles of Olive Oil. The wall in the background says, "Balsamic Vinegars"
So many flavors of oils and vinegars! Taste them all!

TLC Casuals

Right next door to Olivada, look for TLC Casuals at 635 Riverfront Dr.  Owner Tami Conard opened this shop in 1996.  TLC Casuals carries women’s clothing and accessories.  There is plenty to choose from, and you’ll find everything from dressy outfits to jeans and casual items.  One thing’s for sure, TLC’s items are unique and special. 

A women's clothing shop with wood-beamed ceiling and many racks of women's clothing.
So many unique and beautiful fashions!

Harbor Center Marina and Bar 43

When you’ve had your fill of fun and sun and are ready for a late afternoon cocktail to cool down, head for the marina at 821 Broughton Drive.  Not only is this the perfect place to catch a stunning view of the boats docked in the harbor, but there is no better view than that from Bar43, which sits on the top floor of the Marina.

Enjoy the view while sipping a Signature cocktail in this clean, upscale (and air-conditioned) cocktail lounge.

a view of a boat harbor over Lake Michigan - taken from the deck at Bar 43.
I could sit and sip and watch this view all day!
A circular sign with the words Bar 43 Cut in and a blue light showing through - all hung on a very dark, wooden wall
A Lakewiew Experience for sure!


Sheboygan is a town full of culture.  They have some of the most unique and progressive museums I’ve seen in my travels throughout the Midwest.  I only had time to visit a few, so let me know in the comments below if I’ve missed your favorite.  If you’ve never been to Sheboygan, any of these will be a wonderful experience, leaving you wanting more.

The John Michael Kohler Arts Center Art Preserve

I find it hard to come up with the words to describe the incredible experience of a walk through the John Michael Koehler Arts Center Art Preserve.  This world-class arts center opened in 2021 and is the first in the world of its kind, focusing on collections of art rather than individual pieces.  A wander through this art museum allows you to get a peek into the minds of the artists behind their works.

I won’t lie – this museum is a bit of a macabre experience, which gave me an uncomfortable shutter now and again.  You’ll walk away with a different perspective on the artists and their works.  The building itself is a work of art with giant pillars artistically arranged at the entrance.  Three floors house the over 25,000 works of art in the preserve, so give yourself ample time to explore.

Although you may find this a strange recommendation, trust me when I tell you to stop at the first-floor restrooms for a happy surprise.  I promise you’ll be delighted.  I’ll give you a tiny hint:  The Kohler name is significant in Sheboygan.  You’ll find the Kohler name on everything from Kohler-Andrae State Park to this museum.

Above & Beyond Children’s Museum

If you have the grandkids with you, the Above and Beyond Children’s Museum is the place to be, and you can’t miss this fantastic building just a short walk from WordHaven at 902 N. 8th Street!  The outside is adorned with a giant whale mural, and a ship appears to protrude from the upper story.

The inside is a multi-level playscape for children and the perfect way to get them involved in active play and away from their screens.  Look for the honey farm, the circus car, a fortune teller station, and many other imaginative play areas.

The front side of a classic building in Sheboygan with a boat protruding from the upper portion.
I love that boat sticking out of the top!
a brick building with a giant mural of a whale on the back side of the Above & Beyond Children's Museum
The boat continues through the building and out the backside.

The All-Abilities Purple Octopus Playground

Directly next to the museum building is the Purple Octopus Playground, which opened in the spring of 2022.  The playground is as functional as she is gorgeous, covered in bright purple, and filled with activities that work for kids of all ages and all abilities.  Even this Hip Grandma wanted to climb and explore!

The Purple Octopus All-Abilities Playground in Sheboygan, Wisconsin showing a purple octopus on a bed of blue created into a playground
A photo doesn’t do this playground justice. Such a beautiful place, meant for everyone!

Restaurants and the Best Place to Stay in Sheboygan

Your visit to Sheboygan will keep you so busy that you’ll work up a hearty appetite.  Some favorite dinner spots on my visit were Lino Ristorante Italiano, Il Ritrovo Pizza (a more casual Italian restaurant), and the Black Pig.  For breakfast or lunch, check out Seeboth Deli.  For all my restaurant recommendations in Sheboygan, read Nine Best Restaurants and Places to Eat in Sheboygan, Wisconsin

If you are looking for a place to stay in Sheboygan, look no further than the Blue Harbor Resort and Conference Center.  You will be treated like royalty and have the best view of the Lake when staying with them. 

All the Rest

Bask on the Beaches

One of the top things to do on a trip to Sheboygan is to visit at least one of the fantastic beaches in town.  One of my favorite places is Kohler-Andrae State Park, complete with a nature center.  I love the sand dunes, the nature trails, and the sandy beaches that make up this beautiful state park that your whole family will love. 

Sheboygan is nicknamed the “Malibu of the Midwest” for good reason.  The beaches of Sheboygan are all unique and gorgeous.  Pick a beachside park along the Lake Michigan shoreline and enjoy some unique water sports like kiteboarding and surfing, or choose a park with a picnic area and grill up a burger while you enjoy the great outdoors!  For more information on my favorite beaches of Sheboygan, read The 5 Best Beaches to Visit in Sheboygan, Wisconsin.

Acuity Flag

A trip to the city of Sheboygan isn’t complete without a stop at the world’s tallest symbol of freedom, the Acuity flag. The flag itself measures 70 by 140 feet and holds the distinction of being the world’s largest free-flying American flag.  Of course, to fly this 250 lb. beast of a flag, one needs a beast of a flagpole.  And that’s precisely what this flagpole is.  Standing 400 feet tall (100 feet taller than the Statue of Liberty), the pole weighs 420,000 pounds!

I will tell you from personal experience that this flag is enormous and will take your breath away!  I visited on a gorgeous fall day, and it was beautiful.  Be sure to take a short walk to the nearby display to read all the stats and facts about the Acuity Flag!

The enormous acuity flag on display in front of a clear blue sky.
It’s impossible to gauge how large this flag is from this image.
The author grins with an open smile and points over her head at the Acuity Flag.
This moment definitely calls for a selfie!
Showing the size of the base of the Acuity flag - a giant pole with four women stretched out around the front
We fit 9 of us stretched out around the base of this flat. Huge! Photo credit: Rachel Stankevich

Bookworm Gardens

If you love books and the outdoors, greenery and imagination, then you’ll love Bookworm Gardens.  This whimsical garden is open from May 1 through October 1, so make sure you plan your visit accordingly.  Bookworm Gardens isn’t your ordinary garden space.  You’ll want to set aside enough time to explore when you visit.

As you wander through the garden, you’ll very quickly notice that there’s a theme.  This botanical garden space’s curators have based everything you see on favorite children’s books.  Wander, and you’ll find the Three Bears, Harold and his purple crayon, the Three Little Piggies, the Little Blue Truck, and many more in the 70 different gardens.  I wandered for at least a few hours and found new details around every corner.  Mixed in with the beautiful plant life are sculptures, statues, and buildings that will make you smile in wonder.  There’s even a real-live Magic School Bus you can climb in for your own imaginative adventure!  Bookworm Gardens is the perfect place to celebrate your love of books!

Open since 2010; Bookworm Gardens is the perfect place to dream, relax, enjoy the sound of children’s laughter, and soak in nature and a good book.  And they make it easy – each exhibit along the way has a stash where you can pull out a weather-safe copy of the book that inspired the area in which you are located. 

James Tellen Woodland Sculpture Garden

The James Tellen Woodland Sculpture Garden, located at 5734 Evergreen Drive, is an outdoor masterpiece.  James A. Tellen created over 30 sculptures and works of art on his property around the family’s summer cottage.  Wander the trails through the woods to see his many figures, some mythical, some religious, and all unique. 

If you’re lucky, you may get a peek at some natural wildlife as you walk through this wooded area.  I was tickled to see a mother doe and her fawn quietly walking not far from me.  We were not shrieking, but we were not silent in our revelry as we made our way down the first path, and that mother/fawn duo didn’t seem the least concerned about our presence.  Locals tell me this is a regular occurrence on the property.

The site is dedicated to continuing the arts.  Along with the original log home, the property now includes a small, refurbished home structure available as resident artist housing and sometimes for special workshops or educational programs.  The property is beautiful, and I could have spent hours meandering the trails or parking myself at a spot and journaling, praying, or otherwise enjoying the peace and serenity.

the author poses with a cement statue of Abraham Lincoln
Well, hello Abe!
a brick-like structure made with cement of an arch and a man with a deer.
I loved this work of art depicting a deer.

The Lottie Cooper Shipwreck Site

The Lottie Cooper is a Great Lake three-masted schooner that capsized off the shore of Sheboygan in 1894.  Her wreckage was discovered as Sheboygan began planning to construct the marina built in 1992.  Enough remains were recovered to create an 89-ft section that is now on display for public viewing.  While you wander through Deland Park, walk over to see the Lottie Cooper Shipwreck Site.

Walking through the recovered boards that re-form her into her original size is a unique experience for sure and one you won’t want to miss.  And one of the best things about this stop?  It’s free to check her out!  You can learn more about Lottie Cooper’s story HERE.

Brown tones of every shade on display with the pieces of the Lottie Cooper.
The Lottie Cooper display is really cool to walk through!
The author wanders through the Lottie Cooper Shipwreck with her camera
You can see how large this shipwreck really is!

Mead Public Library

The Mead Public Library is beautiful, but the best part is the warm welcome you will receive when you enter.  Peruse the bookshelves, attend an activity or a class, or find a cozy corner to cuddle up in and enjoy quiet time.  The Mead has convenient free public access computer stations and laptops and offers free Wi-Fi, and makes a perfect place to recharge and plan for the rest of your day.

Wrapping it all Up

When you plan your trip to Sheboygan, make sure you give yourself plenty of time to explore!  This town will keep you plenty busy for days.  Sheboygan is top-notch, from the arts to the outdoors and everything in between!  For even more ideas than those here, stop in at the Sheboygan Visitor Center, where the friendly folks of Visit Sheboygan can direct you to any indoor or outdoor activities your heart desires!  This Visitor Center is clean and new and a fun stop.  You can even pick up a souvenir created by one of the local artists of Sheboygan.  When you stop in, tell them the Hip Grandma said hello!

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