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 On the Water: SUP, Surf & Kayak 

Sheboygan has been called the “Malibu of the Midwest” and “Fresh Water Surf Capital of the World” for good reason. It boasts some of the gnarliest waves on the Great Lakes that draw surfers from all over the world. 

Lake Michigan is also a great spot for kayaking, windsurfing, sailing or stand up paddle boarding (SUP) along the coast or up the Sheboygan River. EOS Surf Shop, the first shop of its kind in Wisconsin, offers equipment rentals as well as surf and SUP lessons, which are recommended for Great Lakes newbies. Call 920-208-SURF for availability and reservations. EOS also has a seasonal rental dock, open mid-June through Labor Day, located right on the Sheboygan River. The rental dock is staffed every day in summer. Here you can get fitted for a wetsuit and rent surf boards or SUP boards by the hour. 

After you’ve had your fun on the water, snag one of four recreational fire rings along Lake Michigan’s shoreline for a beach bonfire. Located north of Deland Beach near North Point Park, the fire rings are free for public use without a permit from Memorial Day weekend through August. 

Labor Day Surf Weekend

This unofficial party kicks off the start of Lake Michigan surf season with surfers from around the country gathering at Deland Park. “Fall is the best time [for surfing],” says EOS Surf Shop Owner Mike Miller. “We need wind to make waves, so you got to chase it a little bit, you got to be patient.” The waves are worth the wait, especially as summer transitions to fall. “We don’t claim it to be ocean-like, but there are days when we get good, clean waves. Sheboygan has good beaches that aren’t too busy, perfect for the wave sports we do.” 

Five Ways to Play in Sheboygan

1. See a shipwreck up close

In April 1894, a three-masted schooner named the Lottie Cooper capsized and sank in gale force winds just off the Sheboygan Harbor. During the planning of the marina nearly 100 years later, her remains were discovered and a large portion are now on public display at Deland Park.

2. Hit the water park

Locals and visitors alike flock to Sheboygan Quarry Park when the weather warms. This water park and beach is a longtime Sheboygan institution now under new ownership. The family-friendly park offers giant inflatables and slides for visitors age 6 and up, as well as a shallow swim area and plenty of beach for relaxing. Kayaks and stand up paddle boards are available for rent. New owner Mike Miller has plans to eventually expand the on-land offerings with zip lines and a climbing wall. Open mid June through Labor Day. 

3. Explore Indian burial mounds

Just south of Sheboygan is Indian Mound Park, where visitors can see 18 rare animal and geometric Indian burial mounds. The burial mounds, located across 15 acres, date to about 500-750 A.D. One mound displays an exposed burial with artifacts. Take a self-guided tour on the walking path and stroll the boardwalk nature trail through the wetlands.

4. Witness literature come to life

Bookworm Gardens is made of 65 garden spaces inspired by beloved children’s books such as The Giving Tree, Winnie the Pooh and Where the Wild Things Are. Visitors can hop aboard the magic school bus, meet the three bears and create their own world with Harold and a purple crayon. This magical garden is an affordable option for families with children of all ages. Open seasonally from May 1 to October 31, admission is by voluntary donation. 

5. Charter a fishing boat

Fishing on Lake Michigan (otherwise known as “the big pond”) is a year round affair. The summer fishing season will produce Brown Trout, Chinooks, Rainbows and Cohos. In the fall, salmon move upstream to spawn which can be a major boon for fishermen and women who are after their prize catch. Visitsheboygan.com has a list of charter fishing companies to choose from, but they fill up fast for the season, so make sure to book your trip in advance.