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11 Fun Things to Do in Sheboygan County, WI

Experience the vast entertainment scene found in east central Wisconsin.

By Lindsey Hyde on May 9, 2023

Yoga on the beach - Sheboygan
Courtesy of Sheboygan County EDC

Nestled in east central Wisconsin along the edge of beautiful Lake Michigan is Sheboygan, a midsize city ripe with entertainment. In fact, sprinkled throughout the city and its surrounding county are attractions that one would expect to find in a much larger region — think excellent dining establishments, a diverse arts scene and a wide array of outdoor recreation options.

Ready to experience Sheboygan for yourself? Whether you have a local zip code or are just spending a weekend here with friends, here are 11 fun things to do in Sheboygan, WI.

1. Explore Lake Michigan

Ocean-like views, sounds of crashing waves, warm, powdery sand and refreshingly cool water — Lake Michigan is a beach-lover’s oasis. Found on the east side of the county, this great lake is a place for both relaxation and thrills. For a little R&R, bask in the sun or take a leisurely stroll along its sandy beaches. As for the thrills, the choice is yours — go for a swim, try your hand at sailing or paddle a kayak until your arms get tired. Also something worth experiencing? Surfing! During the winter, the lake becomes the perfect place to ride a wave.

The Wisconsin Room Sheboygan
Courtesy of Sheboygan County EDC

2. Grab a Bite

The local fare in and around Sheboygan doesn’t disappoint. The Wisconsin Room, an upscale restaurant found in Kohler, features delicious farm-fresh cuisine for breakfast and dinner. The menu changes often to offer guests the best of what’s in season (think freshly caught fish and ripe strawberries). Another great place to dine? Antonio’s Sports Bar & Grille. Located in Plymouth, this restaurant serves up mouthwatering pizza, sandwiches, wraps, burgers, pasta and more.

Stefanie H. Weill Center for the Performing Arts Sheboygan
Courtesy of Sheboygan County EDC

3. Catch a Performance

Found in the heart of Sheboygan is the Stefanie H. Weill Center for the Performing Arts, a nonprofit theater that features various films, emerging artists and national touring acts, like Little Big Town and the National Ballet Theater of Odessa. It’s a favorite venue among locals and draws visitors from far and wide. Plus, thanks to the venue’s downtown location, attendees are in walking distance of restaurants and other attractions.  

Hiking in Sheboygan
Courtesy of Sheboygan County EDC

4. Take a Hike

Itching to lace up your sneakers and enjoy the great outdoors? Good news — Sheboygan County is full of trails and forests just waiting to be explored. Kettle Moraine State Forest offers a slew of hiking and biking paths that weave through rolling hills, prairies, forests and more. Other great options include the 17-mile Old Plank Road Trail, 14-mile Interurban Trail, and 3.35-mile LaBudde Creek Segment, which is part of the Ice Age Trail.

Whistling Straits Sheboygan
Courtesy of Sheboygan County EDC

5. Grab Your Clubs

Golf isn’t just a pastime in Sheboygan County, it’s part of its identity. Destination Kohler, a local resort that attracts golfers of all skill levels, is home to four of the top 100 courses in America — all designed by well-known golf course architect Pete Dye. These courses include The River, Meadow Valleys, The Straits and The Irish. This venue has also hosted two U.S. Women’s Opens, a U.S. Senior Open, three PGA Championships and the Ryder Cup.

6. Go Snowmobiling

When the weather turns cold and the snow starts to fall, Sheboygan takes on a whole new demeanor. Residents bundle up in coats, hot chocolate becomes a go-to beverage and sparkling snow blankets the region in white. While some might choose to stay warm and cozy inside, exploring the region’s wintry landscape is also a must-experience activity. In fact, the county offers 228 miles of public snowmobile trails.

Road America Sheboygan
Courtesy of Sheboygan County EDC

7. Catch a Race at Road America

Road America, a permanent road racing track in Plymouth, offers excitement like no other. This 640-acre park hosts events such as the IndyCar Series, NASCAR Cup and Xfinity Series, IMSA SportsCars, MotoAmerica and GT World Challenge America. While here, attendees can utilize the area’s on-site campsite, cabins, concessions and much more.

Kohler Chocolates Sheboygan
Courtesy of Sheboygan County EDC

8. Sample Some Chocolate

You haven’t truly experienced chocolate until you’ve tasted the decadent confections crafted in Sheboygan County. Victorian Chocolate Shoppe in downtown Sheboygan sells 80 varieties of homemade hand-dipped chocolates. Its signature product is a truffle, which comes in 27 flavors, from cherry cheesecake to Irish cream. Another must-visit shop is Kohler Chocolates, which serves up terrapins (similar to turtles) in flavors including original buttery, blackstrap, java and peanut butter. While you’re there, make sure to also try the shop’s decadent hot chocolate and ice cream.

3 Sheeps Brewing Sheboygan
Courtesy of Sheboygan County EDC

9. Grab a Local Beer

Need a brewsky? The Sheboygan region is home to several brewing companies that serve up some delicious brews. The Plymouth Brewing Company offers a wide selection of unique beers, from a pistachio nut brown ale to a peanut butter and chocolate imperial stout. Also a favorite among the locals is 3 Sheeps Brewing Co. in Sheboygan. Its dog-friendly taproom makes it the perfect place to grab a drink with friends and their pups. Try the Chaos Pattern hazy IPA or the Bon Bon stout. 

10. Check Out Miesfeld’s

Given that Sheboygan is referred to as “The Bratwurst Capital of the World,” sampling a local brat is considered a must-do activity. Miesfeld’s Triangle Market has been part of the Sheboygan community since 1941, and its national award-winning brats are quite the crowd-pleaser. Brats come in flavors like garlic, nacho cheese, caveman, jalapeno cheddar and chorizo.

John Michael Kohler Arts Center Fair
Courtesy of John Michael Kohler Arts Center

11. Attend a Festival

The calendar is packed with fun events throughout the county each year, from live music in the summer to holiday fests in the winter. One that comes back year after year is the Midsummer Festival of the Arts, which is held on the grounds of the John Michael Kohler Arts Center and the City Green. The event features more than 100 artist booths, where attendees can enjoy and purchase artworks and meet their makers.

This article was sponsored by the Sheboygan County EDC.

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