A Girls' Weekend Trip in Sheboygan

If you’ve been searching for an excuse to plan a girls' trip, here is your sign! Sometimes, nothing beats quality time with your girlfriends, and going on trips to destinations both new and old is the best way to create memorable events all together! From dining out, to day activities to do together, I have suggestions for an entire girls' weekend prepared. I’m here to tell you all the reasons why Sheboygan should be your next girls trip destination, and to provide some inspiration for outings to plan. Mostly everything suggested in this blog is applicable for all four seasons, only a couple are best suited for the spring or summertime.

Lake Michigan Retreat

Sheboygan is the small-Midwest-coastal town of your dreams: beaches that stretch up the shoreline of Lake Michigan for miles, cute little cafes to linger at, art museums to wander, creative activities in the heart of downtown, and all of it just a short walk or drive from unique dining. Girls' weekend trips should always include a balance of lingering over food and drinks, a fun and unique activity to partake in during the day, the perfect photo taking opportunity, a bit of shopping or exploring, and either an evening out on the town, or a cozy night in with all your favorite snacks and drinks.

Begin Your Girls' Weekend With Coffee

My girlfriends and I like to ease into our day lingering in a café, and Paradigm is the café to go with the girlies. Coffee, tea, smoothies, and even some bubbly, their menu includes just about any drink you prefer to start your days with. What’s more than that, is their menu ranges from gluten-free, to vegetarian, to vegan. No matter the dietary needs in your friend group, everyone will be able to order brunch complete with a bakery treat. The seating both indoors and outdoors is quite accommodating to groups of people, so if you have a longer list of girls attending your trip, you can easily find a spot to seat you all. Plus, the atmosphere is cute and artsy for any and all photos you take together.

Experiential Activities for Your Girls' Getaway

After lingering over a sweet treat and your beverage of choice, it’s probably late-morning or midday; time to fit in an experiential activity!  For groups that like to be artistic, head over to Board and Brush for a painting project you get to bring home as a memento of your trip together. You can upgrade this experience to a paint and sip with either alcoholic or non-alcoholic beverages to enjoy together while you paint.

For those who enjoy art but feel a little less artistically inclined themselves, the John Michael Kohler Arts museum is a fun and beautiful destination that will captivate you for a whole day. And talk about photo opportunities! The environment from the gardens outside to the lobby- (even the bathrooms!) are beautiful, atmospheric, and unique.

If you and your girlfriends enjoy active and wellness-focused activities, sign up for a class at Elevate Yoga all together (and get a group photo of everyone in their cute workout sets). Sheboygan also has a lakeside walking trail with parks and beaches along the way that you could walk together, making pit stops on the sandy beach or in the marina for a picnic.

Insta-Worthy Selfie Locations in Sheboygan

If you didn’t get enough photos during your afternoon activity, I have more than a couple of suggestions for photo op destinations around Sheboygan. Sheboygan is the Malibu of the Midwest, so getting photos on the beach is a must. Deland park is a public beach nestled between the downtown area and the Sheboygan River, so it’s a great place to stop for beachy photos before catching your dinner reservation. Sandy beaches and lighthouse views really complete the scene, and it’s located right next to the marina. One of my favorite bars is in the marina lookout tower, Bar 43, and if you head up to get a drink you can get lakeside and city-wide shots from the 3^rd level of the lookout tower.

Cross the Sheboygan River to get to South Pier Drive where more beach awaits just behind Blue Harbor Resort. Blue Harbor’s grand staircase descends onto the beach and the walking trail alongside the beach- it’s the picturesque place for a group photo. It’s size alone guarantees that everyone will be able to be seen in the shot.

For more city views, head to 8^th Street downtown to take gorgeous photos with historic buildings, greenery, and street art. Keep your eyes out for the murals scattered around the historic downtown.

Shopping in Sheboygan

Overall, whether you choose the beach, Blue Harbor, or 8^th Street as your photo-taking destination, you’ll be a short walk or drive to the list of shops, bars, and restaurants the reside in and around downtown. Boutiques, cosmetic businesses, kitchen shops, game shops, and bookstores, you’ll be hard pressed to contain your shopping to just an hour. Some of my favorite shops that would be on my list to stop at are the Mainstream Boutique, WordHaven BookHouse, Nikki’s Nex 2 New, The Gameboard, Olivü 426, and the Victorian Chocolate Shoppe.

If you're reading this in April 2024, the Sheboygan Harbor Center BID's Spring into the BID gives shoppers who shop at the Riverfront, South Pier, the Boutique at Blue Harbor, and Downtown the opportunity to enter to win a $250 shopping spree. All you have to do to enter is provide proof of purchase from any of the participating stores during the month of April for the chance to win. Click here to learn more.

Gather the Girls for Ladies Night

There are enough stores for you to shop until you drop, and thankfully, you can drop right into your seat for dinner. For eating out, I recommend The Black Pig, Il Ritrovo, or Trattoria Stefano. Il Ritrovo and Trattoria Stefano serve authentic Italian dishes that truly make you feel like you’re in Italy. The Black Pig serves a variety of dishes such as burgers, salads, pastas, noodles, steak, and salmon. The full bar will keep you sipping all night, and their cocktail list has some of the most flavorful and unique drinks in Sheboygan.

For the ladies that prefer a night in over a night dining and drinking out, one can never go wrong with ordering pizza. Faye’s pizza is a Sheboygan favorite that also offers delivery. On top of that, their homemade pizzas can be customized to be gluten free.

Faye’s is located near 3 Sheeps Brewery, and if staying in and having some locally crafted beers and seltzers are in the cards, then pick up a case of 3 Sheeps to share with your girlfriends at home while chatting and watching your favorite movies.

After writing this, I’m feeling the itch to host a girls’ weekend with my friends, and I hope that you feel excited and inspired to take a girls trip to Sheboygan yourself!