By Trent Modglin

When I was in my 20s living in Chicago, my roommate was from Milwaukee and we would go up every few months to bar hop with her friends and hang with her family. It was a friendly city and all, but nothing about Milwaukee ever wowed me except maybe the annual Summerfest music lineup. But that’s not the case now. Far from it, actually. Milwaukee’s impressive transformation over the last decade or so has my family wanting to stay a bit longer each time we visit. A combination of modern meets historic, it’s got a lot to offer these days. Here are a few of our favorite spots:

We happened across the 3rd Street Market Hall by accident the first time, but it’s in our regular rotation now thanks to its self-serve beer wall, food vendors, shuffleboard and bags, and rentable rooms for simulated games. Bonus: They recently added a stand-up comedy club for national acts.

St. Paul Fish Company lobster roll at the Milwaukee Public Market

Speaking of must-stops, the Milwaukee Public Market is probably at the top of the list. This diverse market is always teeming with energy and an enormous selection of high-quality, freshly prepared food from local vendors.

Speaking of must-stops, the Milwaukee Public Market probably is at the top of the list when we’re in town. This diverse market is always teeming with energy and a great place to peruse an enormous selection of high-quality, freshly prepared food from local vendors. Grab yourself an eye-catching bloody Mary and save room for a lobster roll from the St. Paul Fish Company.

A walking exploration of the 10 square blocks of the historic Third Ward (and the Riverwalk) is a perfect way to burn off those calories from the Public Market, and the galleries and shops are plentiful, including an Edie Boutique on Broadway Street. Highly recommend the brunch at the comfortably hip Café Benelux. A table on the spacious rooftop here is coveted territory when the weather is right. The Explorium Brewpub near the river has solid food, as does a hidden gem called Swingin’ Door Exchange. And there’s a Colectivo coffee shop across the street from the market if you want a latte for your walk.

The Milwaukee River and the beautifully restored warehouse and factory buildings that line its path to the lake have undergone quite a facelift over the last decade, and a narrated boat tour from Edelweiss Cruises is a relaxing and informative way to experience the city’s bridges, shoreline, historical landmarks, yacht clubs, skyline and Summerfest grounds.

After you depart the Edelweiss boat, stop by the Wisconsin Cheese Mart on Water Street to take home some of the state’s finest.

If the weather’s nice, we usually take a stroll through Veterans Park on the lakefront. Fly a kite, ride a swan paddle boat or maybe stumble across a festival like we have on more than one occasion.

If the weather’s nice, we usually take a stroll through Veterans Park on the lakefront. Fly a kite, ride a swan paddle boat or maybe stumble across a festival like we have on more than one occasion.

If you have younger kids, Discovery World can be a pretty engaging and interactive way to spend part of the day between its aquarium, exhibits, simulators and more.

Cafe Benelux rooftop in the historic Third Ward

Milwaukee’s Brewery District makes for a nice walking destination if you can handle a few hills — especially if you include a tour of the Pabst Brewery — and some of our favorite beer makers in town include MobCraft, Central Waters, Lakefront, Third Space and Wizard Works.

Milwaukee is also home to Traveling Beer Gardens that move to different parks every couple weeks in the summer and serve beer out of iconic Sprecher Brewery fire trucks. Beer garden classics like pretzels and brats are available, as well as goodies from local food trucks. Visit on a Friday or Saturday night for live music.

The beautiful and charming 131-year-old Pfister Hotel has an extensive history of hosting presidents and entertainers, as well as great views from the 23rd-floor lounge and the largest Victorian art collection of any hotel in the world.

For lodging, in the past, we typically would choose a random hotel that was equal parts affordable and close to our plans. That was until we stayed at The Pfister Hotel for the first time. The beautiful and charming 131-year-old hotel has an extensive history of hosting presidents and entertainers, as well as great views from the 23rd-floor pool and lounge and the largest Victorian art collection of any hotel in the world. And rest assured, off-peak prices aren’t as bad as you’d think.

Another hotel we love is the County Clare Irish Inn & Pub in the Yankee Hill neighborhood just north of downtown. Even if you don’t stay there, the inviting pub and restaurant is worth a visit (order the fish and chips). Especially when there’s live Irish music.

The Pfister Hotel