The Best 24-Hour Trip That Will Make You Want to Stay in Downtown Sheboygan WI

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The Best 24-Hour Trip That Will Make You Want to Stay in Downtown Sheboygan WI

If you find yourself in Wisconsin on a road trip and need a place to stay, look no further than the city of Sheboygan!  With this 24-hour itinerary, you’ll have everything you need to get a bite to eat, explore, shop, and even stay the night.  You may even want to stay longer than 24 hours after this tour!

A little about Sheboygan

Sheboygan is a city in Wisconsin known for its beautiful scenery, rich history, and friendly people.  Founded in 1835, it was a significant center of the lumber industry in the 19th century, as evidenced in the historic downtown district.  Downtown Sheboygan and the surrounding areas are perfect for exploring on a quick trip. 

Located on Lake Michigan, Sheboygan, and its shores are lined with beautiful beaches and parks, perfect for outdoor activities.  The city also has several state parks, including Kohler-Andrae State Park, known for its stunning dunes and forests.

Known for its midwestern-friendly people, Sheboygan has a strong sense of community, and you’ll find plenty of smiling faces here!  Who doesn’t love a town where its residents are always willing to help out their neighbors?

Where to Stay

Watershed Hotel

I like to begin with where to stay when visiting a new town so you’ll know where your home base is.  In the Sheboygan area, you must stay at the Watershed Hotel.  

The Watershed Hotel in downtown Sheboygan Wisconsin

 This 25-room boutique hotel is situated on the Sheboygan River, where you can enjoy lovely views of the River.

My favorite part of the Watershed Hotel is its focus on reducing environmental impact.  Their eco-friendly focus means using energy-efficient appliances, lighting, and water-saving fixtures throughout the property.  Watershed also uses recycled materials in its construction and furnishings, which helps to reduce its environmental impact.

Ongoing eco-friendly efforts include recycling and composting programs, which help to reduce the amount of waste that goes to landfills.  They also use local and sustainable food sources and purchase and use green cleaning products. You won’t have your room cleaned from top to bottom every day, but your cleaning needs are taken care of at your request.

The Watershed Hotel is committed to being environmentally responsible, and its eco-friendly features make it an excellent choice if you want to reduce your environmental impact. I love this!

Finally, Watershed Hotel is dog-friendly and has its own resident dog on site.  Hugo, an English Cream Golden Retriever, is a special temporary employee living at the Watershed while he trains to become a service dog for a child with autism.  Say hello to Hugo when you visit.

838 N 15th St, Sheboygan, WI

Interior of the Watershed Hotel in downtown Sheboygan Wisconsin

Where to Eat


Weather Center Café

The Weather Center Café is a quaint little coffee shop on the Sheboygan River just a few minutes from the Watershed Hotel.  Locals know that the best place to enjoy your cup of coffee in the summer is on the deck, where you can view Lake Michigan and the mouth of the Sheboygan River.  The warm and welcoming staff will fix you up a delicious breakfast.  Their menu has some traditional items and some unique and special options.

I am always a fan of yogurt with granola, and when I visited, I enjoyed a piece of made-on-site carrot cake to finish my healthy breakfast.  I mean – it has carrots.  What more could one ask for in a healthy breakfast!?

The Weather Center is not a fancy breakfast joint.  You’ll order at the counter and wait for your food, but what they lack in pretension, they make up for in deliciousness.  And, of course, free WiFi!  The Weather Center is an excellent option for a relaxing breakfast, coffee or tea, and a local favorite.

809 Riverfront Dr, Sheboygan, WI


Sly’s Midtown Saloon

After a morning of fun, you’ll need to refuel.  Ask anyone in the town of Sheboygan, and they’ll tell you that a Bratwurst is a perfect option.  Why a brat?  Easy!  Sheboygan, Wisconsin, is the Brat Capital of the World!  And the best place to get a good brat plate is at Sly’s Midtown Saloon

Slip on into this pub and belly up to the bar, and prepare to be stuffed.  Sly’s serves a double brat plate with two Sheboygan brats, grilled to perfection and served on a soft roll.  The brats are then topped with cheese, sauerkraut, or onions.   You will enjoy a scoop of potato salad and a pot of buttered baked beans alongside your brat.  Top it off with the dill pickle spear, and you will be stuffed and ready to move on to your afternoon or evening activities.

508 N 8th St, Sheboygan, WI

a plate with two brats, a bowl of baked beans, a scoop of American potato salad, and a pickle spear.
The Brat plate at Sly’s


The Black Pig

A long day’s entertainment best ends with a relaxing dinner and a cocktail or mocktail; the Black Pig, located on 8th Street downtown, is just the right place.

The Black Pig is known for its creative comfort food, including a weekly taco night, unique and delicious burgers, and cocktails in a sizeable brick-walled space.  The Black Pig was opened in 2013 by Chef and Owner Rob Hurrie. Rob has created a place where people can not only fill their bellies but fill their souls with an artful dining experience.

Every dish created at the Black Pig is created from scratch with love and passion, highlighting the ingredients’ distinct flavors and details. Eating at the Black Pig is more than a meal. It’s an experience, and I promise you won’t be disappointed in your experience. That’s a Hip Grandma promise!

multi-colored background with the words "let's be friends" printed on top with "click here to join the facebook group"

The Black Pig’s menu changes frequently, but it always features a variety of creative comfort food dishes.  The most popular menu items include pork belly tacos and mac and cheese.  Be sure to try the Truffle fries, too!  One thing that makes the Black Pig so popular is the amazing service.  Pair that service with delicious food, and you’ll be glad you came!

821 N 8th St, Sheboygan, WI

a sandwich board sign sits on a sidewalk - with a black pig and the words Black Pig - Open Lunch & Dinner
I always loved pink pigs – now I love the Black Pig, too!
a square white plate holds a giant pile of skinny fries with crumbled bacon atop.
Truffle fries. mmmmmmm…

What to Do


Surf Lessons at EOS Surf Shop

There is a reason that Sheboygan is known as the Malibu of the Midwest!  Because Sheboygan is located right on the water of Lake Michigan, it is the perfect location for unsalted, shark-free surfing fun!  Who needs California when you can be part of the surf crowd right in Sheboygan!?

If you’ve never surfed, there’s no time like the present to try.  Local EOS Surf Shop is the perfect place to find all the gear you need and a lesson in how to use it.  They offer a variety of lessons for all levels of surfers, from beginner to advanced.  They also offer private lessons if you want more individualized attention.

Pack some sunscreen and a waterproof phone case, and get photos and videos of your experience!  Be sure to bring some dry clothes along, because as you might imagine, you’ll be good and wet when you finish!  But nothing beats a day on one of Sheboygan’s sandy beaches in the sun.


Axe Throwing and Escape Rooms

Is there a better way to spend an evening than in a unique playground for adults?  You’ll find that at the Longhouse Axe Bar.  The story behind Longhouse Axe Bar in Sheboygan, WI, is one of passion and determination.  Owner Jeremiah Reynolds always dreamed of opening his own business.  After spending a few too many years in a not-so-rewarding job, he found inspiration and worked to create a unique and fun experience for people of all ages.

Belly up to the bar and sip your favorite cocktail.  The atmosphere is welcoming and inclusive.  Longhouse Axe Bar isn’t just about the axes, either.  In 2022, the lower level became home to two unique, challenging escape rooms.  I had the pleasure of getting a sneak peek last year while they were in development, and trust me when I tell you, they are incredible!

Reynolds spent months researching and planning before opening Longhouse Axe Bar in 2018.  He wanted to create a safe and enjoyable bar and worked hard to ensure his vision came to life.  Longhouse Axe Bar is more than just a place to throw axes or try an escape room.  It is a place where people can come together to have fun, make memories, and connect with others.

If you want a unique and fun experience in Sheboygan, WI, check out Longhouse Axe Bar.  Tell Jeremiah the Hip Grandma Sent you!

1133 Indiana Ave, Sheboygan, WI

The author aims an axe, ready to throw
Ready, Aim, Throw!!!
Pink background with "Hip Grandma Merch" available on front

Wrapping It All Up

Sheboygan, Wisconsin, is a beautiful city located on the shore of Lake Michigan.  The city has many attractions, including the sand dunes, the Great Lakes, and the Lake Michigan shoreline.  As promised, you’ll want to stay once you spend a day here.  But don’t worry, if you can’t make it happen this time, know you will always be welcome to return.

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PIN image for 24 Hours in Downtown Sheboygan Wisconsin with four photos - french fries, a brat plate, the weather center cafe and a beach scene - along with the title of the post.

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