Milwaukee On My Mind

Every year, some city gets crowned the next it, underrated, or up-and-coming destination. Sometimes, those accolades feel earned. Other times, they feel like an insult—like the only thing that makes a place valuable is outside validation. Just because something isn’t on your radar doesn’t mean it’s worth less to the people who already know its value.

Take Milwaukee.

I’ve lived in Chicago for the last four years, and in that time, I’ve absolutely fallen in love with our younger sibling to the north. If I’m being honest, I used to think of Milwaukee the same way a lot of people do—beer, bratwurst, the Bucks, and not much else. I knew it was politically important; every four years, Wisconsin becomes the center of the universe, and Milwaukee’s voters help decide the future of the country. But I never thought about the city beyond that.

That was a mistake.

Milwaukee is so much more than just a place that makes headlines when elections roll around. It’s a city with history, character, and grit. A city that doesn’t ask for permission to be great. And every time I visit, I leave wondering why more people aren’t talking about just how special it is.

Milwaukee — A Thief of Hearts

The first time I really saw Milwaukee, I was walking along the RiverWalk downtown — in the dead of winter 2012. The sun was setting, reflecting off the ice, and the whole city felt like it was glowing. It was one of those moments that made me stop and think, why don’t more people talk about this place like this?

Milwaukee surprises you. It doesn’t try too hard. It doesn’t need to be flashy. It just is—a city that knows exactly who it is and isn’t worried about proving itself to anyone.

The Grit and the Charm

Milwaukee has long been defined by its blue-collar roots—built on beer, manufacturing, and hard work. And while that history is still deeply woven into the fabric of the city, it’s not the whole story.

Walk through the Historic Third Ward, and you’ll see cobblestone streets lined with boutiques, coffee shops, and some of the best restaurants in the Midwest. Go to Walker’s Point, and you’ll find craft breweries, cocktail bars, and industrial spaces that have been transformed into some of the most creative spots in the city. The RiverWalk connects it all, winding through downtown, past dive bars and sleek new developments, proving that Milwaukee is evolving while staying true to itself.

And then, there’s the lake.

Lake Michigan in Milwaukee is something else entirely. It feels closer here—more personal. Bradford Beach is packed in the summer, filled with volleyball players and sunbathers, but even on quiet days, it’s stunning. The Milwaukee Art Museum stands right on the water, with views that make you forget you’re in the Midwest at all.

More Than Beer (But Also, the Beer)

Look, I’m not going to pretend Milwaukee isn’t a beer town. It is — and it should be. You can’t come here and not get a High Life at a dive bar. But Milwaukee’s food scene is so much bigger than that.

The first time I had a snapping, cracking bratwurst at Vanguard (2659 S Kinnickinnic Ave, Bayview) with my friend Jackie, I was blown away. It’s the kind of dining experience that feels effortless—creative without being pretentious. La Merenda (125 E National Ave, Walker’s Point) serves up globally inspired small plates in a cozy, unassuming space, and it’s the kind of restaurant that makes you want to stay for hours. If you’re here for brunch, Blue’s Egg (317 N 76th St, Jennings Village) is the move—just get there early because the line is no joke.

I can’t even begin to describe the borderline cosmic, culinary adventure that is the Milwaukee Public Market (400 N Water St, Historic Third Ward). The St. Paul Fish Company… wow. New England should be very, very afraid.

The Energy of the City

Milwaukee knows how to have fun.

Maybe it’s because it doesn’t take itself too seriously. Maybe it’s because the people here are just fun (ahem…Jackie, James, Caroline, Cecelia, Emily!). But whether it’s a spontaneous street party after a Brewers win, a random festival celebrating Milwaukee’s German heritage, or just a packed Brady Street bar on a Friday night, this city has an energy that feels infectious.

Even in the winter—when it’s cold enough to make you question your life choices—Milwaukee finds ways to keep things interesting. Cozy cocktail bars, lively Bucks games, and a surprisingly great underground dining scene make it worth braving the weather.

Milwaukee isn’t up-and-coming. It’s already there. If you’re not paying attention yet, you should be.

Getting There

• From Chicago— Amtrak’s Hiawatha departs hourly from Union Station, arriving in downtown Milwaukee 75 minutes later.

• From Minneapolis— Amtrak’s Borealis and Empire Builder depart three times per day from St. Paul’s Union Depot.

• From the East Coast— Multiple daily flights from major hubs, 1.5 hour flight.

• From the West Coast— Multiple daily flights with layovers in Chicago and Minneapolis.

Where to Stay

• The Pfister Hotel – A Milwaukee icon with old-school luxury and an incredible art collection.

• Saint Kate – The Arts Hotel – A boutique hotel that feels like an art exhibit you get to sleep in.

• The Kimpton Journeyman – Modern, stylish, and located right in the heart of the Third Ward.

• Aloft Milwaukee Downtown — Next to the Fiserv Forum and Old World Third Street.

Where to Eat

• Sanford – A James Beard-winning gem with a rotating menu.

• La Merenda – Cozy, creative, and perfect for sharing plates.

• Blue’s Egg – If you don’t get brunch here, you’re doing it wrong.

• Vanguard — The best bratwurst I have ever had, shout out to Jackie and James!

• The Milwaukee Public Market — if you can’t find something you love here, that’s your problem.

Where to Drink

• Wolski’s Tavern — A famous dive on the Lower East Side, stay until close for the famed bumper sticker.

• This Is It! — Without question, the most iconic LGBTQ+ bar in the city, owned by Trixie Mattel.

• Pufferfish — A posh rooftop on the 6th floor of the Hotel Metro, to die for in the summer months

• The Garage — A Brady Street staple, go get hosed!

• Lost Whale — Eco-focused cocktail bar serving up creative drinks, plus local beers and wines.

• Brian’s Cocktail Lounge — A local favorite with an endless menu of vintage & creative cocktails.

Things to Do

• Miller Brewery Tours — The historic caves are a must.

• Milwaukee Art Museum – Stunning inside and out.

• Harley-Davidson Museum – Even if you don’t ride, it’s fascinating.

• Lakefront Brewery Tour – More fun than any brewery tour has a right to be.

• Bradford Beach – The perfect spot for a summer day, it truly puts a Florida beach to shame.

• The RiverWalk – A scenic way to take in the city.