A Weekend in Milwaukee, Wisconsin

After my trip to Columbus, Ohio a few years ago, my eyes were opened to the joys to be found in the Midwest. In fall of 2019, it was announced that the next Society of American Travel Writers meeting would be in Milwaukee, Wisconsin, so I got excited about seeing a new city. Unfortunately, the event was postponed for a while, but a few weeks ago, I finally got to see the place people jokingly refer to as a “Chicago suburb.”

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What to See and Do in Milwaukee

Because I was in town for a conference, I didn’t get to see as many attractions as I would have liked, but some of our evening events were inside museums.

Best Place– The first thing I did when arriving in Milwaukee was to walk to the former Pabst Brewery for a tour. The historic buildings have been preserved and stand as a reminder for the company’s past. Best of all, you get a beer with your visit!

Cheesehead Factory Tour– Have you wondered about those foam cheesehead hats that Green Bay Packers fans wear? You can visit the place where they’re made and see the process firsthand.

Harley Davidson Museum– Did you know that the classic American motorcycle comes from Milwaukee? The sprawling museum has rare early bikes, jackets from motorcycle clubs, and even models that you can sit on for a photo. Get your ticket before you go.

Historic walking tours– Historic Milwaukee leads tours of the city’s old neighborhoods that show off the diverse range of architecture found here.

Milwaukee Boat Line– This tour operator guides visitors through the city’s waterways on the Milwaukee River and Lake Michigan. There are guided architecture tours, cocktail cruises, and live music cruises.

Milwaukee Art Museum– The building itself is an architectural wonder, with white sail-like features and a bridge to street level. Inside, the museum boasts over 30,000 pieces from antiquity to the present.

Mitchell Park Horticultural Conservatory– Centered around the iconic glass domes, this garden showcases a variety of plant life including tropical and desert species.

National Bobblehead Museum & Hall of Fame– This quirky museum has bobbleheads of everyone from politicians to athletes to characters from your favorite television shows, movies, and even commercials.

Where to Eat in Milwaukee

There’s more than just cheese to be found in Milwaukee. There are so many different types of cuisines, especially in the Brady Street area and within the outer neighborhoods.

Ardent– Often cited as one of the top restaurants in the city, Ardent has an intimate dining room where guests enjoy artfully prepared dishes that change seasonally.

Damascus Gate– The Syrian restaurant is beloved in the community for its traditional Middle Eastern dishes, including kebabs, hummus, falafel, fatayer (a pizza-like dish), and Turkish coffee.

Don’s Grocery and Liquor– This restaurant and speakeasy is in a former corner store and has burgers, brunch, and Old Fashioneds served in Crock Pots. The speakeasy has 10 cent martinis every week, along with a Friday fish fry.

Lake Park Bistro– This former garden pavilion is now one of the city’s most scenic dining destinations. The menu features French-inspired dishes like mussels, goat cheese tarts, and roasted duck.

Milwaukee Public Market– The city’s most famous food hall has dozens of stalls, including seafood, Mediterranean, Mexican, Thai, and vegan.

Real Chili– Popular with the late-night crowd, this local chain dates back to 1931 and serves chili in mild, medium, and hot varieties poured over hot dogs or on its own.

Sobelmans– This eatery is known for over-the-top Bloody Marys, topped with sliders, chicken wings, and asparagus spears. The menu also has massive burgers.

Three Brothers– The James Beard award winner is located in a former Schlitz tavern and is known for its Serbian cuisine like roasted chicken and suckling pig. Note that it’s cash only so come prepared.

Looking for more suggestions? Eater’s Essential 38 includes the city’s best restaurants.

Where to Drink in Milwaukee

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There’s no doubt that Milwaukee is a drinking town. The tailgating culture is massive and the city even has its own version of the old fashioned, made with brandy. And don’t forget about the beer barons that kicked off American brewing.

At Random– Open since 1964, this cocktail lounge maintains its midcentury style. Here you’ll find classic drinks, alongside new varieties.

Bryant’s Cocktail Lounge– Another classic Milwaukee experience is this James Beard-honored bar, which opened in 1938. It’s known for its Pink Squirrel, a sweet and creamy drink made famous here.

Foundation– Embrace the tiki at this bar, which serves one of the city’s best Mai Tais. The interior is covered in Polynesian decor and artifacts.

Lakefront Brewery– Milwaukee’s original craft brewery since 1987 sits on the river, not the lake, but serves incredible beer and food. Don’t miss the famous tour, even though you won’t seen the bottling line from Laverne & Shirley.

Lost Whale– This bar has a funky interior and a playful menu of Midwestern favorites and holiday-themed drinks.

Safehouse– Embrace the kitsch at this spy-themed bar and restaurant where you’ll be required to know the password or perform a series of tasks to gain entry. The drinks fit the theme and the labyrinth of rooms have a series of clues on the walls.

This Is It!– Wisconsin’s oldest LGBTQ+ bar, open since 1968, is owned by Drag Race star Trixie Mattel. The bar hosts weekly watch parties and regular drag shows.

Twisted Path Distillery– Owned by a former CIA agent, this distillery’s tasting room shows off its unique products, including chai-infused vodka, a Bloody Mary-infused vodka, and a cocktail made from snap peas.

Von Trier– The German-style tavern has what you’d expect, beer, along with classic and hot cocktails. They also have German food.

Where to Shop in Milwaukee

Shop for unique souvenirs and locally made goods all over Milwaukee.

Alive and Fine– The funky vintage store has clothing and gifts for men, women, and children.

Antique Center– The sprawling antique mall in the Walker’s Point neighborhood is a must-see.

Bittercube– This locally owned bitters company has a storefront at their factory with all of their products, along with bar tools and curated spirits.

The Bronzeville Collective MKE– Located in Milwaukee’s historically black neighborhood, this store is made up entirely of small businesses and black-owned brands.

Lela Boutique– Find something new or vintage to wear at this locally owned boutique.

Where to Stay in Milwaukee

Milwaukee has an abundance of interesting hotels with rich histories. You can’t go wrong with any of them!

Brewhouse Inn & Suites– Set on the former Pabst brewing campus, the hotel has its own outdoor beer garden, free daily breakfast, and WiFi.

Hotel Metro– Part of the Autograph Collection, this Art Deco-inspired hotel is close to the Milwaukee Art Museum. Guests can enjoy the rooftop deck and sauna.

Kimpton Journeyman Hotel– The Kimpton hotel has a popular rooftop bar along with perks like rental bikes and the daily happy hour for guests.

The Pfister Hotel– One of Milwaukee’s most beautiful historic hotels has been carefully preserved. The hotel has its own spa, a world-class art collection, and a martini bar.

Saint Kate Arts Hotel– Located in the heart of downtown, this art-filled hotel has a champagne bar, a pizzeria, and stylish rooms. There are also coffee makers and water fountains on every floor.

Airbnb– Enjoy staying in a local home or apartment in one of Milwaukee’s trendy neighborhoods.

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