15 Fun & Unique Things to do in Sheboygan, WI

Where to Stay in Sheboygan, WI

When you’re tired after a long day of exploring all of the amazing things to do in Sheboygan Wisconsin, there are a few great hotel options.

My top picks are:

Lake Orchard Farm Retreat *****
Fairfield Inn & Suites Sheboygan ***
La Quinta Inn by Wyndham Sheboygan ***

But if none of those work for you, you can check out my guide on the best hotels in Sheboygan and the surrounding area.

Alternatively, if you prefer a vacation rental, this gorgeous Lake House has beach access to Lake Michigan.

1. Visit Elkhart Lake

Sheboygan is home to some of the most fantastic lake resorts towns in Wisconsin, and one of the best is probably Elkhart Lake.

Located just 20 miles – about a 25-minute drive – from Sheboygan you can easily do Elkhart Lake as a day trip.

Based on the name, you would be forgiven for thinking it’s just a lake, but it’s also a small village!

Elkhart Lake is perfect for visiting at any time of the year, whether you want to enjoy the summer sunshine, hike in the winter snow, or see the flowers bloom in the spring.

No matter when you visit there is something truly special about Elkhart Lake.

If you love the great outdoors, you will be taken in by the natural beauty of this beautiful Wisconsin village.

You can spend the day hiking or a weekend camping, and if you’re into fishing, make sure to actually go out on the lake.

As well as the stunning nature, Elkhart Lake also has some fantastic museums, including the Historic Depot and Museum, Historic Race Circuit, and Henning’s Cheese Museum, among others.

If you decide to stay overnight in Elkhart Lake, you should consider The Osthoff Resort, which is one of the top lake resorts in Wisconsin.

2. Hike Kohler Dunes Cordwalk

Sheboygan, Wisconsin, is home to some of the best wildlife in the state and happens to have one of the most unique Southern Wisconsin hiking trails: The Kohler Dunes Cordwalk.

The Cordwalk runs through the Kohler Dunes State Natural Area, which is part of the Kohler-Andrae State Park.

This 2-mile hike looks easy but can range from medium to difficult throughout, making it one of the best Sheboygan, WI things to do for those who love hiking.

Although you can go off the path, be careful not to disturb the wildlife as this is a protected nature area.

Additionally, the Cordwalk has been placed to allow people to take the best pictures and see the best views.

If you want something easier or shorter the Woodland Dunes Nature Trail is nearby and is another one of the best hiking trails in Wisconsin.

This is an easy hike, half the length, and suitable for wheelchairs and strollers.

3. Explore Kohler-Andrae State Park

The Cordwalk runs through Kohler-Andrae State Park, one of the best state parks in Wisconsin.

Although it’s actually two parks managed as one unit, it is comprised of two parks: Terry Andrae State Park and John Michael Kohler State Park.

Together, they form Kohler-Andrae State Park, which is 998 acres of some of the most incredible natural beauty the state of Wisconsin has to offer.

This state park is located by Lake Michigan, one of the best lakes in Wisconsin, and is home to sand dunes and golden beaches.

But, if you want more greenery, it’s also filled with thousands of trees and animals- many of the latter calling the former their home. 

Its location makes it an ideal place to enjoy fun day trips from Milwaukee. 

Whatever outdoor activities you’re into, you can likely do them at Kohler-Andrae State Park, including camping, fishing, hiking, and picnicking.

You could even go hunting so long as you have the correct license.

So long as you love nature, Kohler-Andrae state park has something to offer you.

If you happen to visit in autumn, the park is one of the best places for fall colors in Wisconsin. 

4. Enjoy a romantic getaway in Sheboygan

Are you after romantic getaways in Wisconsin? If so, there are plenty of romantic things to do in Sheboygan.

It doesn’t matter if you’re going for a honeymoon, anniversary, or just for the sake of it.

There are plenty of romantic Sheboygan things to do for couples to reconnect or just enjoy each other’s company.

Of course, every couple is different, but here are a few ideas to make a romantic getaway in Sheboygan extra special.

Take some time to relax and let all of your stress go at the Blue Harbor Resort and Spa, which is one of the best spa resorts in Wisconsin.

Not only can you get calming couples massages, but you can have a blast together at the on-site waterpark.

If you prefer something even more intimate, then book a stay at the Lake Orchard Farm Retreat.

This cozy lakeside hotel is one of the most romantic hotels in Wisconsin.

There are also a few of the best romantic cabins in Wisconsin located nearby.

If you have your romantic getaway during the summer, make sure you come to the Levitt Amp Sheboygan Music Series.

This is one of the coolest Sheboygan events and has a day dedicated to couples; on Thursday they play romantic music.

When you get hungry, there are also plenty of fantastic places to eat in Sheboygan you can pick from.

A few of the best restaurants in Sheboygan for a romantic night out are Trattoria Stefano, Harry’s Prohibition Bistro, and Umi Sushi And Steak House. 

And to walk it all off, just take a moonlit beach walk hand in hand.

5. Do some fishing on Lake Michigan

The city and greater county of Sheboygan might just be your destination if you like lakes and fishing.

Enjoying a relaxing afternoon on Lake Michigan is a must for any fishing enthusiasts visiting Sheboygan, and is a great family activity in the city.

Although there are a few options along the shore to go fishing, the best option for visitors is to rent a charter boat and go out on the water instead.

If that sounds fun but daunting, don’t worry, there are also options to go out with an instructor who can show you the ropes.

It doesn’t matter if you’ve been fishing all your life or if this is the first time, the instructors will teach you how to fish and ride the boat.

Whether you catch the biggest fish you’ve ever seen or one small enough to fit in the palm of your hands, all that matters is you have fun whilst catching them.

However, please be aware that if you want to fish on Lake Michigan, you need a “Wisconsin Great Lakes Fishing License”.

Some of the fish you might catch on Lake Michigan include Lake Trout, Yellow Perch, Bowfin, Smallmouth Bass, and Largemouth Bass. 

In addition to fishing, make sure to enjoy the fantastic view from the water!

During winter, you can also try out ice fishing on Lake Michigan, which is a unique Wisconsin experience.

6. Spend an afternoon at Bookworm Gardens

If you are looking for the best Sheboygan kids activities, Bookworm Gardens should be top of your list!

Bookworm Gardens states that their amazing gardens are inspired by children’s literature, the natural world, and the imagination, and this is the perfect description.

Wandering through this unique botanical garden in Sheboygan is both fun and educational for adults and kids alike.

Plus, it’s a great way to get kids excited about reading!

Unfortunately, the gardens are only open between May 1 and October 31, so not suitable for anyone looking for fun things to do in winter in Wisconsin.

However, for anyone looking for things to do during spring break in Wisconsin, this might be a great option.

7. Take a look at the art at the John Michael Kohler Arts Center

If you have an eye for modern art, make sure you come down to the John Michael Kohler Arts Center!

This non-profit museum displays modern art made by artists from Sheboygan and beyond. However, preference is given to local artists whenever possible.

Check what’s on when you’re visiting because they often put on displays dedicated to a specific artist.

Everyone is welcome at the arts center, and no knowledge of art is required.

In fact, the John Michael Kohler Arts Center is all about inspiring people to love and appreciate art in all its forms.

This is one of the many incredible Sheboygan attractions for a rainy day, or even if you want to be indoors to escape the sun in the summers.

And, of course, it’s one of the best things to do in Sheboygan, Wisconsin for art lovers.

8. Visit some of Sheboygan’s Winter Resorts

If you like skiing or snowboarding, some of the best ski resorts in Wisconsin are within one hours drive from Sheboygan.

A little further south is Little Switzerland in Slinger, which is the oldest ski resort in Wisconsin.

This incredibly welcoming and hospital resort also has some of the best snowmobile trails in Wisconsin. 

If skiing isn’t your thing, Sunburst in Kewaskum, WI, is home to the world’s largest tubing hill, and one of the best winter things to do in Sheboygan with kids.

Alternatively, for something romantic, you could treat yourself to The American Club at Kohler Waters Spa, which is one of the best winter resorts in Wisconsin.

9. Learn about history in the Railroad Museum

Today, downtown Sheboygan is a modern, vibrant city filled with culture and stunning natural beauty.

But what many people don’t know is that it also has a rich history with the railroads.

Whenever I visit a new place, I always like to learn about the history and culture of that place.

The Sheboygan Railroad Museum is one of the best Sheboygan attractions for stepping into the past and learning about the local history.

You can learn about the different types of trains and their role in Sheboygan’s history at this museum.

It’s strange to think how much the world has changed in just the past 100 or so years.

If you ever have a question about trains or Sheboygan’s railroad history, feel free to ask one of the museum’s lovely staff, who are knowledgeable and friendly.

The museum is one of the best things to do in Sheboygan for history buffs, or anyone looking to escape bad weather.

10. Relax on the beaches in Sheboygan

Sheboygan is home to the best beaches in Wisconsin, and a great spot if you’re after a freshwater beach. 

Located by Lake Michigan, there is no shortage of Sheboygan beach options!

Although there are lots of great beaches, here are some of our favorite beaches in Sheboygan:

Kohler-Andrae State Park

I mentioned the Kohler-Andrae State Park as a great place for hiking and exploring the outdoors, but it’s location on Lake Michigan, also makes it perfect for beach-goers.

With golden sand and stunning waters, it’s the perfect place to set up for a picnic.

Plus, the sand dunes make for great insta-worthy photos!

Deland Park
Deland Park, part of North Point Park, is another Sheboygan beach you might want to venture into.

Some folk like to come along and just soak up the sun, but it’s also an ideal spot to bring along a surfboard and ride the waves if the weather is good.

From Deland Park, you’ll be able to see the Sheboygan Breakwater Lighthouse, one of the best lighthouses in Wisconsin.

King Park Beach
Compared to the other two, King Park Beach is slightly quieter, but that just adds to its appeal.

In addition to swimming, this is a fantastic place to have a picnic or a gentle walk.

11. Enjoy a beer and a bite at 3 Sheeps Brewery

One of the best adults-only things to do in Sheboygan is to have a beer at the 3 Sheeps Brewery.

This small, friendly, local brewery creates some absolutely delicious beers and is a Sheboygan staple.

This is the perfect spot to hang out with friends or a partner after a long day of hiking or exploring.

But even if you’re visiting Sheboygan alone, you can still go and make some local friends.

The brewery also puts on regular events, including a monthly beer and yoga class, which anyone over 21 is welcome to attend.

Don’t forget to learn about how this fantastic local beer is made when you visit the brewery. They are proud of their beer and happy to tell you all about it!

Just some of the beers you can try include Chaos Pattern, Fresh Coast, Pendulum IPA, Waterslides, Steppin’ Out, Super Nova, Infernal Racket, Tiki Time, Bon Bon, and The Wolf.

12. Try and escape from Escape Sheboygan

When you hear the phrase “escape room,” you might picture something horror-based, scary, and filled with jump scares – but not here!

The strategically designed rooms at Escape Sheboygan are based on logic rather than gore.

In fact, they are very adamant that none of the rooms will ever be horror-based, and instead it is one of the best escape rooms in Wisconsin for those who love good old-fashioned logic puzzles.

So there are no scary clowns or loud bangs, just cryptic clues that you and a group of friends or family members need to solve before the clock runs out.

If you all want to get out on time and win, you will need to put your minds together to complete the mystery and unlock the door.

13. Combine art, history, and nature in the James Tellen Woodland Sculpture Garden

Walking around the James Tellen Woodland Sculpture Garden is one of the most unique things to do in Sheboygan.

This small section of forest is home to 30 different concrete-coated wood statues that are inspired by events and people from history, mythology, and religion.

Set in the Black River area, James Tellen Woodland Sculpture Garden uses the beauty of nature as its stage.

It removes art from being something that lives in a museum to something that belongs to everyone.

Some of the statues that you might see include:

• The nativity scene. A man and an animal stand over the manger where baby Jesus lay. 

• A log fence with Native Americans. There are several interpretations you could make from this. But, there is no denying that the craftsmanship is incredible. 

• A woman and a cowboy. The cowboy is talking to her as she does her washing.

14. Enjoy Fall Activities in Sheboygan

If you’re looking for fun Wisconsin Fall Getaways, Sheboygan is a great option for families and couples alike.

One of the best things to do in Sheboygan in the fall is Al & Al’s Oktoberfest, which usually happens around the first week of October.

This Oktoberfest-inspired festival is one of the biggest Sheboygan events of the year and one of the coolest fall festivals in Wisconsin.

Sheboygan has other fun things to do in Wisconsin in October and fall in general, including apple picking, pumpkin patches, hayrides, and a haunted house.

And, of course, head to Kohler-Andrae State Park or Elkhart Lake to marvel at the stunning fall foliage, one of the top fall activities in Wisconsin.

15. Play a few board games at The GameBoard

Board game cafes have been growing in popularity and Sheboygan has welcomed the craze with its very own: The GameBoard.

The GameBoard is perfect for any board game enthusiast, whether you want to come to play board games with friends or make new friends.

Even if you’re new to the game, it doesn’t matter as all the rules are included and you can take your time learning how to play.

This is also a great way to find out if you like a game before you buy it.

So feel free to mingle with the good people of Sheboygan and have fun playing one of the many board games on offer.

If you come at the right time, you can even participate in one of their tournaments or listen to a keynote speaker.

But, even if nothing is on when you visit, spending an afternoon at the cafe is still one of the best things to do in Sheboygan if you love board games!

Sheboygan is a unique city that manages to perfectly combine its natural beauty with the bustling heart of the towns.

Whether you’re coming with your friends, family, or a partner, and whether it rains or shines, Sheboygan will welcome you.

Short FAQ About Things to do in Sheboygan, WI