Four Seasons of Possibility: Sheboygan, Wisconsin

7669
Kitesurfing Sheboygan Wisconsin Malibu Midwest Lake Michigan lighthouse
There is a lot to do in this little town on Lake Michigan from surfing to dining, charter fishing, concerts and more. Visit the www.visitsheboygan.com website to learn all about it.
Global Partner

Are you always on the lookout for new places to travel, interesting communities to explore with watersports environments and cultural experiences to experience? Well, we are too.  Welcome to Sheboygan, Wisconsin, the heartbeat of America and the Malibu of the Midwest. Are you ready for something different?

Stand up paddleboarding Sheboygan Wisconsin lighthouse
Winter, Spring, Summer, Fall: Sheboygan welcomes visitors at every season, offering much to do, see, experience in this great little town known as the ‘Malibu of the Midwest’.

Unique, Diverse, Delicious:  Sheboygan, Wisconsin

Spontaneous, spur of the moment trips can happen at any time. We see one social media post, and get sucked down the rabbit hole, desperate to learn more about a particular travel destination. Well, we are here to help fulfill some travel needs. Hear us out.

Sheboygan, Wisconsin is a unique year-round destination with each season differing from the last. This predominantly German settlement in America’s heartland captures the attention of its visitors with a multitude of lakefront experiences, outdoor treasures, culinary expertise, boutique shops, local events, diverse art scene and, of course, the great people of Sheboygan.

Charter Fishing Visit Sheboygan Wisconsin

Experience the Great Lakes: Sailing & Fishing on Lake Michigan

Let’s start with the summer months in Wisconsin. Summer activities in Sheboygan start as early as Memorial Day Weekend. When the marina fills with boats, visitors know a full season of sailing, fishing, and leisure boating is about to begin. Of course, you’ll want to get in on the action yourself. We suggest, the Sailing Education Association of Sheboygan (SEAS) for an exceptional “First Sail” experience. During this class, participants learn how to prepare a boat for sail, leave the dock/mooring, control a boat in confined waters, interpret navigation rules as well as experience how to control a boat in open waters, implement safety and emergency procedures. It’s one stop shopping for boating procedures!

Or, you can experience sailing in grand style as an option when you reserve a spot aboard the Tartan for a chartered cruise. During your sail, you’ll see Sheboygan’s historic lighthouse, famed skyline, maybe a few kiteboarders, and  – depending on the day – you may catch a sparkle from the sunset as it plays upon the waters of Lake Michigan.

Sailing on the Tartan Sheboygan Wisconsin
Welcome to the Tartan, a unique charter sailing experience on Lake Michigan where you can discover Sheboygan from the perspective of this great lake and experience the special beauty of the sunset.

Sheboygan is bordered on the east by Lake Michigan and hosts from north to south many accessible fishing holes and rivers. There’s fishing for every season in this lakeside community! From casting off the pier, to wading through the waters of local rivers, or escaping onto the lake for a charter excursion, Sheboygan offers multiple one-of-a-kind fishing experiences.

Charter fishing out of Sheboygan is phenomenal and makes us one of the busiest ports on Lake Michigan. A slew of charter captains await to take you out on the lake and pull in your fair share of trophy trout and salmon. If fly fishing is your game, Sheboygan is home to several streams and rivers giving you the opportunity to catch monster trout that have made their way upriver from Lake Michigan.

Paddleboarding Sheboygan Wisconsin Visit Sheboygan mikevang89
Stand up paddle boarding, surfing, and kite surfing are just a few of the ways you can enjoy Lake Michigan along Sheboygan’s fabled waterfront.

History on the River by Kayak or Paddle Board

There are ways to enjoy the river even if you aren’t an avid fisherman. Launch a kayak or paddle board at Kiwanis Park or rent one from the EOS rental dock. EOS Surf & Skate shop fits you for a life jacket and assists first-timers in learning the ropes of paddling. Paddle down the river to see old fishing shanties from Sheboygan’s past. Now, these old shanties, as well as new ones, are home to inviting coffee shops, restaurants, boutiques, and ice cream parlors. The newest additions to the riverfront feature Blue Harbor Resort, mini-golf, festivals, and Sheboygan’s “South Beach.” Both sides of the river have much to offer, old and new.

Riverfront Sheboygan Wisconsin
Enjoy the riverfront in Sheboygan, Wisconsin where old fishing shanties have been turned into restaurants and retail shops, keeping an old school charm in this upscale city.

Live Music & Outdoor Markets on the City Green

If water activities alone aren’t enough for you, there are numerous events that occur in the summer months at Sheboygan. Weekly concerts shake the stage at Sheboygan’s City Green, a unique arts and entertainment green space designed as a meet-up center for tourists, family, friends, and neighbors.  Or, attend the Night Markets, featuring many local vendors, also held at City Green.

Concerts Sheboygan Wisconsin
In summer, catch the weekly concert series outdoors on the green in the middle of the community center. Enjoy the live music, food and beverage in this rich, middle American experience. It will make you proud to call this land your own.

On Mondays all summer, we gather at Vollrath Park to enjoy a feast at the family-owned food trucks famous for food on a stick, in a basket, or wrapped in waxed paper. Honor America’s independence during our Fourth of July FreedomFest. The weekend is filled with parades, live music, family-friendly games, and fireworks.

Brat Days Sheboygan Wisconsin
You can’t leave Sheboygan without testing their culinary favorite, the Brat. Try these tasty treats straight off the grill with sauerkraut and on a home made bun for the experience in this German-settled lakeside town.

The Brat:  Sheboygan’s Culinary Claim to Fame

Late in summer, visitors can celebrate Sheboygan’s claim to fame during ‘Brat Days’. This festival weekend is filled with a variety of free entertainment on three stages, including national entertainment on the main stage. Saturday features activities that are exciting for the whole family including the Brat Trot run, a huge parade, the brat eating contest, a petting zoo, and carnival rides. Hear the roars of NASCARS, Superbikes, and vintage sports cars at Road America’s park-like setting. Watch wheel-to-wheel action with trackside viewing and get up-close access to drivers and teams. Although these are only a few events to be mentioned, more await your discovery at Visit Sheboygan’s events page.

Surfing crew Sheboygan Wisconsin
The surf scene starts in September in Sheboygan. Not for the feint of heart, this hard core caliber crew surfs the lake when the North winds blow catching up to 15 foot swells in formidable conditions.

Cold Water Winter Surf:  It’s a Thing in Wisconsin

Around the time summer ends, Labor Day weekend kicks off the fall season for surfing. Yes, you read that correctly. We surf in Sheboygan. For the past 50 years, the city has affectionately been dubbed the Malibu of the Midwest by the local surfing crowd. You might not expect a landlocked state like Wisconsin to be a haven for hanging ten. However, due to its location and unique shoreline geography along Lake Michigan, Sheboygan features the best waves on the Great Lakes. While there are rare opportunities to surf in the summer due to light winds & swell direction, the optimal experience and the biggest waves happen in late fall through the winter. Do you dare?

Surfing wave Sheboygan Wisconsin
Winter surfing on the Great Lakes is a passionate past-time for so many Sheboyganites and people from the surrounding area. Anybody want to travel to check it out?

Hiking, Biking and Art in Sheboygan

In autumn, around the time our local surf season kicks off, other aspects of Sheboygan also come to life. Hiking is a spectacular fall pastime in Wisconsin. Take time to escape the noise, hit the trails, and gaze upon the fall colors. Maywood Environmental Park, Evergreen Park, Sheboygan Indian Mound Park, James Tellen Woodland Sculpture Garden, and Kohler Andrae State Park each have unique habitats from grassland prairie, sand dunes, forests, and ponds. It all adds up to an incomparable hiking or biking experience.

Fall_Maywood Visit Sheboygan Wisconsin hiking
Taking in the fall colors in one of Sheboygan’s colorful and diverse parks is an excellent way to unwind, and enjoy the present.

When the weather is not cooperating, visitors are encouraged to take a dive into Sheboygan’s art culture. Peek at world-renowned John Michael Kohler Arts Center’s award-winning washrooms. Each is uniquely designed and every year thousands of visitors walk through the museum to experience them as well as other world-class exhibitions. Recently opened, the new John Michael Kohler Art Preserve is home to over thirty-five artist-built environments. However, art does not have to be confined to museums and galleries. In recent years, the street-art movement in Sheboygan has been taking off. Artists use the urban landscape as a canvas for works of art that reflect the city’s people and culture. Our art culture is dynamic and ever changing.

Winter scene in Sheboygan Wisconsin
Sheboygan becomes a winter wonderland once the snow begins to fall. Locals learn to embrace the onset of winter by adding some sparkle to their streets.

Wisconsin’s Winter Wonderland:  Spectacular & Scenic

Eventually, the leaves falling turn into snowflakes drifting to the ground, bringing winter with it to our Mid-Western Malibu. Although it is nice staying indoors by the fire wrapped in a blanket, why not throw on your winter coat, pants, boots, and have some fun? Trudge through the snow at Vollrath Park, a 1930s amphitheater, or enjoy Kiwanis Park for a day of sledding. Each have sets of hills with tiered sides, offering thrilling changes in velocity for sledding on the way down. Or,  you can hit the trails at Maywood with a pair of cross-country skis or snowshoes for a taste of our breathtaking winter scenery.

Then, of course, there’s ice fishing — because how else do you fish in the winter? Lake Michigan’s harbors offer world-class brown and rainbow trout fishing through the ice. Once hooked up, be ready for a long battle! These fish don’t give up easily and they are a trophy only Lake Michigan can offer. Some are upwards of twenty pounds! Inland waters in Sheboygan County offer traditional ice fishing experiences. Try your luck fishing for panfish, northern pike, small mouth, and large mouth bass.

Wine Sheboygan Wisconsin restaurants
Sheboygan’s extensive array of restaurants, pubs, eateries and cafes will keep you nourished and cheerful throughout your stay. There are so many options to explore.

Enjoy Small Town Shopping & Culinary Treats

Later, take shelter from the cold when you browse through all the captivating local shops. Visitors don’t just shop in Sheboygan, they become engaged with the hospitality of small-town entrepreneurs who have selected, commissioned or created each spectacular item for its uniqueness and quality. From make-your-own products to culinary treats to your favorite accessories, shop Sheboygan’s riverfront and downtown for cultural fun in a friendly community setting.

You may even wander into one of Sheboygan’s renowned mouthwatering restaurants. There is simply no way to describe the full culinary experience here. Sheboygan has all the dining and drinking staples one would expect to find in a waterfront destination. Small cafes with charming atmosphere and delicious coffee dot the lake shore. The waterfront hosts classy establishments with water viewing tables and patios proudly offering Italian, Mexican, and American style foods. Libations flow freely among the local bars, breweries, and eateries who pour a wide selection of craft beers, wines, and cocktails. You’ll never go hungry (or thirsty!) when visiting Sheboygan.

3 Sheeps bar tap Sheboygan Wisconsin

Get Dirty & Green:  Farms & Gardens in Sheboygan

After the long winter, it is time to thaw your hands and feet by indulging in the growing season of spring in Wisconsin. Become mesmerized in the fictional worlds at Bookworm Gardens. This vibrant, playful botanic garden is inspired by children’s literature, the natural world, and imagination. Even if you miss the trees sprouting new leaves and flowers blossoming during the spring, you are sure to see picture perfect blooms throughout the summer.

Bookworm Gardens Sheboygan Wisconsin
The Bookworm Gardens offer quiet places to settle with a book or simply be in nature, enjoying the seasonal rotation of blossoms of flowers and trees that thoughtfully design the landscape in Sheboygan.

Looking for a hands-on farming experience? Nourish Farms offer proactive, realistic learning programs to encourage individuals and organizations in our community to make wholesome food choices by growing, cooking, and supporting the local food system. Different tours include experiential learning opportunities that teach how food is grown, focusing on sustainable farming practices. During each tour, participants harvest local produce and enjoy a true farm-to-table meal. If you can’t make it to Sheboygan in spring, don’t fret. Nourish offers programs throughout the year.

Blue Harbor resort Sheboygan Wisconsin
The Blue Harbor resort overlooks Lake Michigan and sits along the main walkway to take you to town, dining and restaurants while offering you the lap of luxe for your stay in Sheboygan.

Lay Your Head:  Lodging Options in Sheboygan

At this point we are confident that you are hooked on wanting to book a trip to Sheboygan. So, where should you stay in Sheboygan? Some of our hotels are located downtown, on the riverfront, or right on the shores on Lake Michigan like Blue Harbor Resort. Take time to walk along the pathways outside or splash around at Blue Harbor’s indoor waterpark. Whether you are looking for thrilling rides or a calming atmosphere, this resort will work to accommodate all of your needs. Or, you can enjoy a stay at Harbor Wind on the river walk or the Grand Stay Suites near shopping, dining, and the arts.

Sheboygan may be known as the Malibu of the Midwest, but it’s also a gem of a four-season getaway.

Written by, Rachel Stankevich  (VisitSheboygan.com)

Check out the FULL 6-page feature on Sheboygan’s winter surf scene in Standup Journal’s FALL’21 issue available for purchase in: BACK ISSUES, HERE.

Mahalo!

 

Previous articleEliminating the Intimidation of The Crossing For Cystic Fibrosis & Fundraising
Next articleWaterchat Podcast : Go Outside to Grow Inside with Courtney Sinclair
Rachel Stankevich, Marketing Manager at Visit Sheboygan, is originally from Northern Wisconsin, but spent her college years in Sheboygan playing basketball at Lakeland University. She is a year-round outdoorswoman and keeps herself busy with traveling, kayaking, hiking, and is starting to take a liking to other sports such as surfing, sailing, and kiteboarding. Her love for travel has inspired her blogs, videos, and advertising campaigns. Her future plans include seeking certification in scuba diving after exploring a shipwreck just off Sheboygan’s shoreline. Rachel almost always has a camera with her to capture her adventures and share them with future visitors. She is constantly visiting new places around Sheboygan to share the area she fell in love with. You can find her most days with camera in hand, hiking trails, savoring the local cuisine, or out on the water.