We had never been to Sheboygan before, but finally made the trip in December! We had the best time wandering around with my sister and brother-in-law. Why is Sheboygan called ‘the Malibu of the Midwest,’ you ask? Well Sheboygan is the Freshwater Surf Capital of the WORLD! Due to its location, Sheboygan gets the best waves of the Great Lakes. You can surf all year long, but it is said ‘prime time’ is in the winter.
I can’t imagine surfing during the Wisconsin winter, but my sister and brother-in-law sounded so stoked about it! We didn’t see anyone surfing while we were there, but here are our recommendations from our visit:
Il Ritrovo: 515 S 8th St, Sheboygan, WI 53081
First and foremost, you MUST plan to eat at Il Ritrovo. This authentic Italian restaurant is to die for and located in Downtown Sheboygan. They strive to use the local, seasonal, and sustainable ingredients, and it shows– all four of us were blown away by everything we ordered. Hayden and I thought it was in the top 3 meals we had in 2022. Order the “Fonduta al Forno” as an appetizer, at least one wood-fired pizza, and a pasta to share. You need to try as much of their amazing food as possible!
3 Sheeps Brewing Company: 1837 North Ave, Sheboygan, WI 53083
We had a really great time at 3 Sheeps! The first thing that really stood out to me was how incredibly dog-friendly it was–there were lots of happy pups around. I had a really good sour beer, but the rest of the group was crushing Fresh Coast! It’s a juicy pale ale that’s one of my brother-in-law’s favorites. Be aware that 3 Sheeps doesn’t serve any food, (which allows them to be dog-friendly,) but you are welcome to bring in your own grub. We ordered wings from Legend Larry’s via DoorDash, and they were so good!
Velvet Sheep Farms: W1681 Garton Rd, Sheboygan, WI 53083
We had a really nice stay at this one-of-a-kind bed & breakfast. It’s an actual sheep farm, and we could see the sheep from our room’s window! We went out to give the male sheep some pets, and they were an entertaining bunch. The room was so cozy and the breakfast was delightful. I would definitely stay again!
Honey and Ace: 817 New York Ave, Sheboygan, WI 53081
While strolling around downtown Sheboygan, we popped into Honey and Ace. This store was adorable and filled with the cutest random things– think: hair clips, earrings, bath salts, and lots more! The coolest part is that they have fun set-ups in the lower level that make for great photo ops. Highly recommend shopping around there!
Wade House: W7965 WI-23, Greenbush, WI 53026
Just 20 minutes outside of town, you’ll find this awesome historic site! The Wade House sits in its original location in Sheboygan County. There are several buildings on the property, and you get to travel back in time to see how this 3 level, 18 room stagecoach inn was run back in the mid 1800s. We strolled all through the beautiful property, and we can’t wait to visit again in the summer to see the animals, sawmill, and blacksmith shop in action!!
Sheboygan Breakwater Lighthouse: 604 N 8th St, Sheboygan, WI 53081
Stroll out along roaring Lake Michigan to the beautiful red lighthouse! You can walk all the way out and it was a great place for a photo even on the gloomy day we were there. It’s a bit further than it looks, so be sure to dress accordingly, as we were a little chilly due to the wind coming off the lake. Right next to the parking lot by the lighthouse is the Lottie Cooper, a preserved shipwreck you can explore!
American Club: 419 Highland Dr, Kohler, WI 53044
We stopped by the legendary American Club and participated in our own (unplanned) little bar hop! We stopped by The Wisconsin Room and had a fancy moment in The Library Bar. The fancy moment came with higher priced cocktails, but it was so worth it to enjoy the renowned Wisconsin Resort. I had the BOLD Old Fashioned and it was super sweet and unique! It’s a classic Wisconsin Old Fashioned using Kohler Original Recipe Dark Chocolate Brandy. After wandering around looking for the bathroom, my sister and I found that The Winery Bar was featuring live music so naturally we made the move there. The cocktail menu was very elaborate and Hayden found a bunch of options even he had never heard of before! After a drink there, it was starting to get late and I was ready for a sweet treat, so we made our way down the hall to the next spot, Horse & Plow. We had another round of excellent cocktails and ordered one of their yummy seasonal desserts! Highly recommend a stop at The American Club, even if it’s just for a cocktail. It is truly a beautiful, luxurious spot in Wisconsin.
WE’LL BE BACK
As always, we didn’t get to go everywhere we wanted to in Sheboygan in just one trip. We will definitely be back to hike in Kohler-Andrae State Park with the pups, explore Bookworm Gardens, and indulge in a sweet breakfast treat at Sunday Dough. Let us know any other Sheboygan recommendations you have for us!
Well there you have it–our Sheboygan recommendations! If you have any questions, let us know, and we will be happy to help you plan your adventures. Be sure to follow us on Instagram for more travel guides and adventure inspiration!