A Weekend in Milwaukee
Beer, cocktails, and music await a quick jaunt north of Chicago
Just 90 minutes north of Chicago lies a small city filled with retro bars, rich food, friendly people, and one of the country’s largest summer music festivals: Milwaukee.
Each summer, hundreds of thousands of people flock to this city in the heart of the Midwest for Summerfest, a two-week-long music festival billed as the largest in the world. Summerfest runs through July 9 this year, and headlining artists include Machine Gun Kelley, Rod Stewart, Cheap Trick, Backstreet Boys, Thomas Rhett, 2 Chainz, A Flock of Seagulls, and more (see the full lineup here).
But Milwaukee is more than a music festival. The city is home to fantastic breweries, Art Deco buildings, and retro bars and restaurants that will have you channeling the 1950s and its most famous son, Fonzie from Happy Days (don’t forget to visit the Fonzie statue, commemorating the city’s famed character).
Where to Stay
The Pfister Hotel
Since 1893, the Pfister has been Milwaukee’s grand dame of hotels. The hotel boasts the largest hotel collection of Victorian art and offers pet-friendly accommodations in the heart of the city. Make sure to have a cocktail at Blu, the 23rd-floor lounge that offers amazing views of the city and lakefront.
Where to Eat
Leon’s Frozen Custard
If you’re itching for a big dose of nostalgia, head over to Leon’s Frozen Custard. This stand has been dishing out the local Wisconsin treat since 1942 — and nothing much has changed. The neon building is perfect for all your Instagram shots, and the custard — richer and creamer than soft-serve ice cream — is a must-try while in Wisconsin.
Milwaukee Brat House
German immigrants brought their rich fare — including sausages — with them when they settled in Wisconsin. The Milwaukee Brat House offers sausages made by local sausage maker, Usinger’s. Your choice includes brats, Italian sausage, smoked sausage, hot dogs, hot Hungarian sausage, and even a vegan sausage. Of course, there’s plenty of beer in giant mugs to wash it all down with. Don’t forget to order a side of Wisconsin cheese curds dipped in batter and fried to a golden brown.
Milwaukee Public Market
Located in Milwaukee’s Third Ward, the Public House is a market that houses cheese shops, butchers, fish mongers, gift shops, and several restaurants. The market also offers culinary classes and has several outdoor bars so you can enjoy a bite and a pint after shopping.
Where to Drink
One of the country’s best tiki bars happens to be located in an old house in a residential section of Milwaukee. Step into Foundation and be transported to the South Seas while you sip on classics like the Jet Fuel, Navy Grog, and Planter’s Punch. Don’t worry if you’ve had one too many — Foundation actually has a mini tiki-themed hotel on the second floor (book through Airbnb).
Lakefront Brewery and Pabst Brewery
Considered the Beer Capital of the World, Milwaukee is no slouch when it comes to both large breweries and small craft breweries. To compare and contrast old and new, visit the Pabst brewery and taproom, then head over to Lakefront Brewery. Usually, brewery tours are dry, but this one features beer samples, a bunch of dad jokes, and a singalong to the Laverne and Shirley theme.
Bryant’s Cocktail Lounge
Bryant’s is Milwaukee’s oldest cocktail lounge. Established in 1938, this lounge (again, hidden inside a single-family house) makes some of the finest cocktails in the city. This is the place to try Wisconsin’s strangest drink — the brandy Old-Fashioned. You can also order a plethora of retro cocktails like the Pink Squirrel, cocktails made with ice cream, and cocktails found only at Bryant’s — like the DeFrongue: a secret drink that comes with its own book of poetry.