On a cool weekday in October, the sun glistened over calm Lake Michigan water beyond pale sands and clusters seagrass. The blue sky was dotted with fluffy clouds. The empty white Adirondack chair provided a wide beach view, including an antique lighthouse in the distance. Sheboygan, Wisconsin becomes more crowded from late autumn into April. Surfers will flock to the Midwest’s Malibu in April. Surprised? Since more than 50 years, Sheboygan’s waters have attracted surfers from around the world. Many of them consider this destination a bucket-list destination.

Sheboygan surfers will have to adjust their buoyancy. Saltwater is more buoyant. Wave volume isn’t bad, even when winds blow from the west or northeast at speeds of 20-25 mph. These surfing waves, however, are not as warm as the ones in Malibu. For optimal comfort, you’ll need to wear a wetsuit from head-to-toe when surfing in Sheboygan.

If you are a beginner surfer, EOS surf & Revolution board shop can help. Wisconsin’s first paddleboard and surf shop has been in business since 1998. They stock everything from Stand Up Paddleboards to surfboards. Rent a wetsuit and/or a board before you go surfing in Sheboygan.

Beyond The Board

Many sailing enthusiasts also launch from the shore, even though this area is not as well known for other water sports. The non-profit SEAS (Sailing Education Association of Sheboygan), aims to make boating accessible for all, regardless of financial, cognitive, or physical challenges.

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The US Sailing standard for power and sailboats is addressed in each class. Winter classes can cover maritime history, water skills, traditional skills, marine industry and preservation.

SEAS is also a partner with Sheboygan Youth Sailing Center and Sheboygan Youth Sailing Center. Sail Sheboygan U.S. is a third partner. The Sailing Center promotes sailing competitions at the national and international level. World Class regattas are hosted by the organization. The organization also provided support and training for the women’s sailing during the 2012 Olympics.

Many fishing enthusiasts flock to local lakes and fishing holes. Outdoor enthusiasts can also enjoy paddling, or exploring local parks.

Sheboygan Surfers’ Stay

The AAA Three Diamond Blue Harbor Resort & Conference Center is an independent property. The resort opened in sprawling buildings that were left by the previous tenant nearly 20 years ago. The white exterior, rounded towers and deep red roofs of this resort reminded me a lot of the Hotel del Coronado in California.

Photo by Lisa Waterman Gray. Photo by Lisa Waterman Gray

The lobby captured my attention. The ceiling was decorated with pale blue paint, fluffy clouds and twin balconies. Patio umbrellas stood above linen-dressed dining tables. This inviting space also has the entrances of restaurants and cafes. The area was decorated with Halloween pumpkins during our visit.

We toured briefly the multi-level, enormous indoor water park in the evening. In the water, floats of bright colors were resting. Stairways connected long slides to either the pool or the ground. A huge snack bar menu was also available to visitors. Guests of the resort receive free passes to the park. Day passes are available.

Breaker Bay Indoor Waterpark is open all year round and offers watery fun. Photo by Lisa Waterman Gray

Blue Harbor is Wisconsin’s only resort on Lake Michigan. Residents of Chicago and Milwaukee are frequent guests. The guests can rent a villa or book a variety of suite configurations. The bi-level accommodation I rented had queen beds both upstairs and downstairs. The walls, carpetings, decorative tiles, and curtains were all decorated in deep blue. The gas fireplace and wall-mounted TV were flanked by a bright red sleeper couch.

Blue Harbor accommodation. Photo by Lisa Waterman Gray

We were shown many suites with stunning views of Lake Michigan during our property tour. Sheboygan surfers can also stay at independently-owned properties like the 25-room Watershed Hotel and Event Center, or the historic The Rochester Inn.

After Surfing in Sheboygan, Enjoy Dining and Drinks

Sheboygan has a solid surfing reputation, but also a number of restaurants and arts enclaves that welcome visitors. In a meeting room at Blue Harbor, our group enjoyed a delicious multi-course meal.

Our group had a delicious multi-course meal at Blue Harbor Resort. Photo by Lisa Waterman Gray.

We waited for our tables in the warm lobby of Lino Italiano on a gray, chilly evening. The authentic Italian meal began with an amazing Caprese salad. Then we shared antipasto plates before my huge plate of Ravioli Burro e Salvia arrived. The butter and sage flavor the spinach and ricotta flavored ravioli. Our group finished with a fresh tiramisu, and a refreshing gelato made from limoncello.

Sheboygan also has brewhouses, sports bars, or you can sample soft-served ice cream, breakfast, deli food, and other treats. The Bourbon Street Pub & Grill serves up New Orleans-inspired food.

Waterless Entertainment

Sheboygan is a city that loves the arts. The free, non-profit John Michael Kohler Arts Center has been operating since 1967. It is filled with contemporary exhibits, family-friendly activities and a decades-old art-based preschool.

Installations made of natural wood and hanging fiber art were among the many we saw. Some of my favourite ‘installations,’ however, were handcrafted tiles that covered the entire wall in public washrooms. I was mesmerized by each of the spaces, whether it be with pale pink tiles and flower buds or elegant female images. Or iconic New York City buildings, praying hands, or armored Knights.

The bathroom tiles at John Michael Kohler Arts Center also featured stunning images. Photo by Lisa Waterman Gray

The art preserve of the John Michael Kohler Arts Center, surrounded by lush trees is an extension to the Arts Center that will open in summer 2021. Our group found that much interior work was still needed to prepare this bright and airy space for the incoming artists.

The entrance to this building, with its soaring timber ceiling, has me captivated ever since we entered the parking area. The entryway is naturally constructed to shield the art from direct sunlight. The 56,000-square foot, multi-level Art Preserve is the first museum in the world ” ” dedicated to the exhibition and preservation of artist-built environments.