“Boaters can’t not visit Sheboygan, Wisconsin”. How’s that for some good old-fashioned Wisconsin “English” (der hey, one-time, doncha know)?
I admit to being born and raised (or as we say “home brewed”) in Wisconsin; having raced sailboats on Lake Michigan from Milwaukee and Sheboygan harbors and being a fervent powerboater on Michigan and inland lakes along with being a 3-decade+ marine industry veteran. Sheboygan harbor has truly benefited from the natural beauty of the area and the meandering course of the Sheboygan river.
The people of Sheboygan and visitors from around the world changed the lakefront and riverside from an older, commercial venue to avoid into one of the nicest ports on either side of Lake Michigan. The changes made to the waterfront area beckon boaters to the harbor, river and into the rejuvenated downtown area whose main street is lined with unique shops and world-class restaurants. If you dock at the marina or along the river, a soft-wheel trolly can take you on the couple minute ride to the heart of Sheboygan or you can just enjoy a leisurely 5-8 minute stroll to get there.
My Italian heritage frequently steers me to 8th street (aka Main Street Sheboygan) to dine at Il Ritrovo, for their wood-fired, stone pizza oven delicacies; Field to Fork deli whose made fresh daily breads are addicting or the seven-star (yes I know you’re supposed to only give a place five stars but…) “trattoria Stefano” Italian restaurant.
You’ll find Sheboygan waiting for you behind its lighthouse at 43.763 degrees north latitude and 87.698 degrees west longitude. It’s on a broad point that reaches east out into Lake Michigan giving it a natural shelter for part of the harbor and amazingly, some of the best surfing on the Great Lakes.
Yes, real wave surfing along the natural sand beach north of the river entrance. Kite surfing and sailboarding 
enthusiasts use the waters south of the river mouth towards “King Park” for their fun. For folks who like being beneath the waves of Lake Michigan, there’s numerous wrecks to explore including the “Atlanta” a 200’ passenger and freight carrier that sank in 1906. “Atlanta” is located just south of Sheboygan in shallow waters.
The point of land left there by the mile-thick glacial action thousands of years ago is extended out into Lake Michigan with a breakwater on both the north and south sides of the harbor and river entrance. There’s a US Army Corps of Engineers project working to repair the south breakwater that should be completed by 2023.
Mike Vandersteen is the mayor of Sheboygan. He is a water and waterfront enthusiast. He is committed to not just maintaining the standard and quality of the Sheboygan waterfront and riverway but to help improving it for generations to come. Mike can frequently be seen touring the many parts of Sheboygan on his bicycle, including the north and south pier areas as he visits with city residents, business owners and visitors.
Between the northern sandy beach and the river is the 281 slip Sheboygan Marina complex, Sheboygan Yacht Club, public launching ramps, fuel dock and one of the finest and most renowned youth sailing centers on fresh water.
The marina is managed by Matt Bauer, a Sheboygan native, and the F3 marina management company. Of the 281 slips, 100 of the slips are kept available for transient boaters. The three-story tall marina building delivers spectacular, cityscape and lakeshore views and houses their offices, lounge, ships store, pool and hot tub area with shower facilities for all guests.
Matt is working on their new bar/cocktail center/lounge on the upper level. It should be open by fall of 2020.
If you don’t want to boat to Sheboygan, you can easily charter a boat to experience some of the best Great Lakes fishing to be had.
There’s a good selection of charter operators on the Sheboygan river along the south pier. Dan Welsch was born in Sheboygan and after high school, 35 years ago, he borrowed some money from his dad to buy a fishing boat and start his charter business.
Today, “Dumper Dan’s” fleet of six Baha Cruisers boats is the largest in Sheboygan and one of the most prolific on Lake Michigan. In 2019, Dan did 1,125 charters. The nearby Sheboygan River and the shallow and deeper waters of Lake Michigan yield Coho and Chinook King Salmon, Brown Trout, Lake Trout and Rainbow Trout, Walleye, Perch, Bluegill, Bass, Pike and Carp. Sheboygan works with the Wisconsin DNR to help with stocking programs to make sure the species of fish stay healthy and plentiful.
Dan has a shop on the river by the boats and to help folks who want to fish with him, has condos available right next door. Just up the South Pier from Dan’s are more restaurants, kayak rental outlets, a way too convenient ice cream shop.
For more information on Sheboygan, Wis., you could just go there and enjoy it but for those who prefer to be prepared a bit more you can check out these links https://visitsheboygan.com/ ; https://www.sheboyganwi.gov/ and don’t forget to check out the video interviews with Mayor Mike Vandersteen, Sheboygan Marina manager Matt Bauer and Dan Welsch of Dumper Dan’s on Great Lakes Boating’s Facebook pages.
See you in Sheboygan…
