One of my favorite traditions each summer is getting together with my Blonde Squad friends for a girls weekend. Andrea hosted our very first get-together at her home in Indiana, and the following two years we explored different parts of Michigan together. This year, we ventured into Wisconsin for a Milwaukee girls weekend, a destination that felt especially meaningful to me. I attended graduate school in Milwaukee and then lived in the suburbs for another eight years, so it was fun returning to some old favorites while sharing a few hidden gems with friends who had never visited before. From lakeside walks and afternoon tea to boutique shopping and great food, it was the perfect long weekend.
Thursday: A Wisconsin Welcome
Since Kathrine lives along the way, I picked her up Thursday afternoon and we started our road trip north. No trip to southeastern Wisconsin would be complete without stopping at O&H Danish Bakery for a kringle, so naturally we made a quick detour. If you’ve never had one, you’re missing out! My favorite flavor is cinnamon roll, and it made a good breakfast option for our weekend.
We rented the cutest Airbnb in Bay View, one of the Milwaukee neighborhoods. Located just a few blocks from South Shore Park and Lake Michigan, it was the perfect home base. It was easy to reach from I-794, which made getting around the city incredibly convenient all weekend.
After unpacking, we headed to Milwaukee’s Intermodal Station to pick up Caroline, who arrived by train from Chicago. By the time we returned, Jill had arrived too. We definitely missed Andrea this year, but we’re already hoping to get everyone together again in Chicago this fall.
For dinner, I introduced everyone to a Milwaukee classic: Sobelman’s. Burgers, fried pickles, and lots of laughs made for a great first evening. Back at the house, we settled onto the upstairs porch with wine and held our annual clothing swap. It was such a fun way to give clothes and accessories a second life while catching up late into the evening.
Friday: Tea, Shopping & Cedarburg
We started the first morning of our Milwaukee girls weekend with a three-mile walk along the lakefront before enjoying Jill’s delicious homemade sausage roll for breakfast.
On our way downtown for afternoon tea, we made a quick stop at Goodwill to pick up interesting vessels for a candle-making project later that evening. The forecast wasn’t looking great, so we wanted a fun indoor activity just in case.
Since we still had time before our afternoon tea reservation, I took everyone on one of my favorite drives in Milwaukee along Lincoln Memorial Drive. We passed the Milwaukee Art Museum, Bradford Beach, the marina, and the beautiful historic homes overlooking Lake Michigan near the UW-Milwaukee campus. It reminded me why I loved living here for so many years.
Tea at the Pfister Hotel was one of my favorite experiences of the weekend. Before we even ordered, each tea was presented for us to smell and learn about before making our selections. Combined with the incredible views overlooking downtown Milwaukee and Lake Michigan, it felt like such a special afternoon.
After tea we drove north to Cedarburg, one of Wisconsin’s most charming small towns. Despite a steady drizzle, we wandered in and out of boutiques and specialty shops until we realized it was already late afternoon.
Back at the Airbnb, dinner was simple with pizza rolls, veggies, crackers, and dip before we transformed our thrifted finds into candles by melting down old wax. My pottery crock, Jill’s vintage pink vase, and Kathrine’s teacup all turned out beautifully. It was such a fun way to repurpose items that otherwise might have been discarded.
Saturday: Rain Didn’t Stop Us
Caroline and I had planned to go for a morning run along the lakefront, but the rain had other ideas. Instead, we enjoyed Kathrine’s incredible French toast casserole before attempting the South Shore Farmers Market.
Unfortunately, the weather kept many vendors away, but I still managed to pick up fresh Wisconsin sweet corn for dinners back home. The market brought back memories of living just a couple of miles away in St. Francis while I was in graduate school.
Once everyone was ready for the day, we browsed a vintage clothing shop in Bay View before discovering some treasures at an antique mall in Walker’s Point.
Lunch at the Milwaukee Public Market was another highlight. With everything from seafood and barbecue to empanadas, there’s truly something for everyone. Before leaving, I stocked up on Spice House seasonings and my favorite olive oil from Oro di Oliva—two places I never skip when I’m back in Milwaukee.
Next came boutique shopping in Wauwatosa followed by much-needed afternoon coffee before heading back to get ready for dinner. We all loved the Salamander boutique!
That evening we dressed up for cocktails at At Random, one of Bay View’s iconic retro lounges, before walking a few blocks to Goodkind for dinner. Between sharing appetizers, entrees, and an amazing waitress who made the evening even more enjoyable, it was the perfect final night together.
Sunday: One Last Run
Sunday morning I finally got the lakefront run I’d been hoping for all weekend. Training for multiple marathons along Milwaukee’s lakefront path made those few miles especially nostalgic. Watching the waves roll in while running along Lake Michigan reminded me why this route has always been one of my favorites.
After one last breakfast together, it was time to pack up from our Milwaukee girls weekend. I dropped Caroline at the train station, took Kathrine home, and officially wrapped up another Blonde Squad adventure.
Wrap-Up
Our Milwaukee girls weekend was the perfect mix of revisiting old favorites and discovering a few new places together. I loved getting to share a city that played such a big role in my life with some of my closest friends, and even rainy weather couldn’t slow us down. More than anything, this annual tradition reminds me how important it is to make time for the people who encourage you, make you laugh, and always leave you counting down until the next trip. Here’s hoping our fall Chicago reunion comes together—and that another girls weekend is already on next summer’s calendar.
Confident Twosday Linkup
Last week’s favorite post was from Cecile at The Frenchie Mummy who shared a cute, sporty outfit.
Between Naps on the Porch | I do de Claire | Walking in Memphis in High Heels & The Fashion Canvas | Tuesday Twirl | My Slices of Life | The Style Splash | Curated by Jennifer | Mummabstylish | Shelbee On the Edge | Nancy’s Fashion Style | Momfessionals | Marsha in the Middle
