Four Seasons of Possibilities



Unique, Diverse, Delicious: Sheboygan Wisconsin

Spontaneous and spur-of-the-moment trips can happen at any time. You see one social media post, and you are sucked down the rabbit hole of wanting to learn more about that destination. Sheboygan is a year-round destination with each season differing uniquely from the last. This German settlement catches the eye of many a visitor near and far with its lakefront adventures, nature exploration, culinary experiences, unique shops, spectacular events, and art culture.

Experience the Great Lakes: Sailing & fishing on Lake Michigan

Let’s start with the summer months in Wisconsin. Summer activities start as soon as Memorial Day weekend. As the marina fills with boats, you 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. The Sailing Education Association of Sheboygan (SEAS) offers an exceptional “First Sail” experience. During this session you’ll learn how to properly prepare a boat to sail, leave the dock/mooring, control a boat in confined waters, interpret navigation rules and tips, control a boat in open waters, implement safety and emergency procedures, and more. Sailing in style is also an option when you reserve a spot aboard the Tartan for a chance to enjoy a blissful chartered cruise. During your sail, you’ll see Sheboygan’s lighthouse, skyline, maybe a few kiteboarders, and depending on the time of day, you may catch a sparkle from the sunset, as it plays upon the top of Lake Michigan.

Sheboygan is bordered to the east by Lake Michigan and is filled from north to south with accessible fishing holes and rivers. There’s fishing for every season and every time of day! From casting off the pier on a calm day to wading in the waters of the local rivers, to escaping to the big lake on a charter excursion, Sheboygan is the place to be for that one-of-a-kind fishing experience. Charter fishing out of Sheboygan is phenomenal and makes us one of the busiest ports on Lake Michigan. A slew of charter captains wait to take you out on the big lake to pull in your fair share of trophy trout and salmon. If fly fishing is your cup of tea, 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.

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 fits you for a lifejacket and even assists first-timers learning the ropes of paddling. As you paddle down the river, you’ll see old fishing shanties from Sheboygan’s past. But the old shanties, as well as the new ones, are home to 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.

Live music & outdoor markets on the City Green


If water activities alone aren’t enough for you, there are numerous events that occur during the summer months. Weekly concerts shake the stage at Sheboygan’s City Green; a unique arts and entertainment green space that’s designed as a meet-up space for tourists, family, friends, and neighbors or attend the Night Markets, featuring local vendors, also held at City Green. On Mondays, gather at Vollrath Park in the summer for family-owned food trucks that are famous for food on a stick, in a basket, or wrapped in waxed paper. Honor America’s independence during the Fourth of July FreedomFest. The weekend is filled with parades, live music, family-friendly games, and fireworks.

The Brat: Sheboygan’s Culinary Claim to Fame

Late in the summer, celebrate Sheboygan’s claim to fame during Brat Days. It is a weekend filled with a variety of free entertainment on three stages, with national entertainment on the main stage. Saturday features activities that are fun 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 that can be mentioned more are waiting for your discovery at Visit Sheboygan’s events page.

Cold water winter surfing: 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 surf crowd. You would never expect a landlocked state like Wisconsin to be a haven for hanging ten. Because of its location and geography, Sheboygan has some of the best waves on the Great Lakes. While there are rare opportunities to go surfing in the summer, the best experience and the biggest waves happen in late fall through the winter.

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 experience. When the weather is not cooperating, take a dive into Sheboygan’s art culture. Peek at world-renowned John Michael Kohler Arts Center’s award-winning washrooms. Each one is uniquely designed and each year thousands of visitors walk through the museum to experience them as well as 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 are using the urban landscape as a canvas for works of art that reflect the city’s people and culture.

Wisconsin’s winter wonderland: spectacular & scenic

Eventually, the leaves falling quickly turns into snow falling, bringing winter into full force. Although it is nice staying indoors wrapped in a blanket, throw on your winter coat, pants, boots, and have some fun. Trudge through the snow at Vollrath Park, a 1930s amphitheater, or Kiwanis Park for a day of sledding. Each set of hills have tiered sides, offering thrilling changes in velocity on the way down. Hit the trails at Maywood with a pair of cross-country skis or snowshoes on your feet for a taste of 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 you better be ready for a long battle. These fish don’t give up easily and they are a trophy only Lake Michigan can offer; some upwards of twenty pounds! Inland waters in Sheboygan County offer traditional ice fishing experiences. Try your luck fishing for panfish, northern pike, smallmouth, and largemouth bass.

Enjoy small town shopping & culinary treats

Later, take shelter from the cold when you browse through all the captivating local shops. You don’t just shop in Sheboygan, you become engaged with the hospitality of small-town entrepreneurs who have personally 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. You may even wonder into one of Sheboygan’s 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 atmospheres and way-good coffee dot the lakeshore. Classy establishments with waterfront tables and patios proudly offering Italian, Mexican, and American style foods. Libations flow just as freely with local bars, breweries, and eateries pouring a wide selection of craft beers, wines, and cocktails. You’ll never go hungry when visiting Sheboygan.

Get dirty & green: farms & gardens in Sheboygan

After a long winter its time to thaw your hands and feet and indulge in the growing season of spring. 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.

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

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 of Lake Michigan, like Blue Harbor Resort. Take some time to walk along the pathways outside or splash around at their indoor waterpark. Whether you are looking for thrilling rides or a calming atmosphere, they are there to accommodate all your needs. Or 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.

About the Author

I am originally from Northern Wisconsin but spent my college years in Sheboygan. I love exploring new places around Sheboygan and I want you to fall in love with the area just as I did.  I always have my camera on me in order to capture my adventures and share them on the blog. Follow along with me as I give you insider tips on some of my favorite places to eat and drink, the best ways to experience Lake Michigan, and so much more.

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