How to Completely Dominate a Trip to Milwaukee
If Milwaukee’s nicknames ("City of Festivals" and "Brew City") don't inspire you to go there, then how about the fact that it's cheap, full of proud and friendly locals, and has more bars than grocery stores? Uh huh, sign us up. This city is rooted in Midwest tradition and history, but with lots of playful experimentation and sophistication -- especially when it comes to the booming restaurant and bar scene.
This year is officially Milwaukee's coming out party, as it hosts the Democratic National Convention in mid-July. Come for the craft breweries and fried cheese curds, but take time to discover the world-class museums, James Beard Award-winning restaurants, the revitalized downtown, and distinctive neighborhoods that make Milwaukee one of our top 20 Best Places for a Big Trip in 2020.
When to visit Milwaukee in 2020
2020 is Milwaukee's time to shine, as the city puts its game face on with improved hotels, public transit, and new builds downtown in anticipation of the DNC. You'll obviously want to AVOID the week of the DNC starting July 13, but it's sandwiched by two of Milwaukee's best festivals. Choose Summerfest -- an 11-day music festival on its own dedicated lakefront grounds -- if you're into seeing national acts for cheap while you dance on bleachers; or go with the Wisconsin State Fair in early August if you'd prefer to eat your weight in foods on a stick and cream puffs. No matter which summer weekend you plan, there will be festivals, from music-centric Irish Fest to celebrations of beer or art.
Day 1: Begin with the most important things: eating and drinking
Fly into the airport, recombobulate yourself, and pick up your rental car, because Milwaukee is very much a driving city. Try to land around lunch time, because there's a wealth of amazing food within blocks of the airport. Try some of the area's best Thai at Kim's, a butter burger with hand-pattied beef with a square of melty butter at old-school Nite Owl (only open for lunch during the summer), or "Milwaukee-style ribs" with the pork belly still attached at Iron Grate BBQ.
If the timing is right, head to a Brewers game on a free Miller Park shuttle from the bars on nearby Bluemound Road, where the beers are way cheaper than in the park. Unless they're playing the Cubs, you'll be able to get tickets at the stadium. Grab a hotel downtown, like the boutique, art-filled Saint Kate.
Day 2: Get cultured and learn about beer
Take your pick of museums and attractions: The Harley-Davidson Museum is interesting and fun whether you're a biker or not, the Milwaukee Public Museum is for natural history buffs, and the Mitchell Park Domes contain three unique botanical ecosystems. Grab some brunch (we brunch every day) just south of Downtown in Walker's Point at Don's Diner & Cocktails or Engine Company 3.
Ride shares are pretty inexpensive here, so plan on using them for a brewery and distillery tour. Great Lakes Distillery has great spirits and Lakefront Brewery is the most entertaining tour in the area (and you'll drink a bunch). If you have any energy left, consider bowling -- a sport with a long history in MKE -- at unique, glorious dive bar/alley combos Landmark Lanes or Koz's Mini Bowl.
Day 3: Hit the lake
Take in one of the city's many festivals, or chill at the downtown lakefront for most of the day. Lake Michigan is so large that it feels like an ocean with smaller waves, so Bradford Beach is the spot to be if it's sunny and hot. Hit up the Gift of Wings kite store in Veterans Park because there's always a breeze off the lake. Rent a paddle boat in the lagoon or wander into the stunning Milwaukee Art Museum, designed by world-famous architect/sculptor Santiago Calatrava.
If you want to explore, jump on The Hop, a free downtown streetcar with 18 stops. Get off in the Historic Third Ward and head to the Milwaukee Public Market for a lobster roll at St. Paul Fish Company, and check out the boutique shops nearby. Need a nightcap? Try cozy, vintage-chic Goodkind for amazing cocktails and late-night small plates, or At Random for an ice-cream drink with a Rat Pack vibe.
MORE:Of course we've got an entire list dedicated to cool things to do in Milwaukee
Day 4: A neighborhood jaunt before flying out
Before you head out, explore one of Milwaukee's neighborhoods that you may have missed while running around. Riverwest is great for avant-garde co-ops, eclectic eats, and some of the best dive bars in the city. Walker's Point is a diverse neighborhood with great antique shops, traditional Mexican food, and colorful murals. And in Bay View, you'll find one of the busiest nightlife strips in the city on Kinnickinnic Avenue -- full of bars, restaurants, shops, and theaters. Any of these neighborhoods would also be worth adding extra time onto a trip to explore.
Keep it going: 3 days in Chicago
Amtrak's Hiawatha service makes it extremely easy to get to downtown Chicago in about an hour and a half. Then you can use the El to easily get around the city. Hit up Millennium Park to take selfies with Cloud Gate, aka "The Bean." The Art Institute of Chicago is just a couple blocks away, and you can easily spend the entire day exploring or recreating Ferris Bueller scenes. Head south for a little stargazing at the Adler Planetarium.
If you want to do the deep-dish thing (though Chicago pizza is about much more than that), you can't go wrong with Pequod's and its caramelized cheese crust, near the Clybourn stop on the Green Line. Score tickets to the The Second City and laugh the night away. It's a big city, and you can do pretty much everything.
MORE: Consult our local edition to plan your Chicago whirlwind
Keep it going longer: 2 days in Madison
Wisconsin's capital city, known for outdoorsiness and huge student population, is only an hour away by car from Milwaukee and 2.5 from Chicago. Walk around the isthmus and head inside the Capitol to see the beautiful rotunda. On Saturday mornings, Capitol Square hosts one of the best and busiest farmers markets in the country. Grab some cheese curds at nearby Tipsy Cow or the Curd Girl cart. As for nightlife, there is a huge number of concert venues in the city, like the brand-new Sylvee, or walk to pedestrian-only State Street and bar hop like you're a college student again. A post-bar slice of Ian's Pizza will help you feel better in the morning.
MEET THE WRITER
Lacey Muszynski is a Milwaukee native who has been writing about her love of Wisconsin for over a decade. Her food, drink, and travel writing and photography has also appeared on Serious Eats, Taste of Home, MSN, and in many local publications.
How long have you been living in Milwaukee? What drew you there?
I was born here, and here I am 36 years later because the Milwaukee vibe just fits me. Milwaukeeans are known to be stubborn, averse to change, and super proud of their city, and that is exactly who I am, right down to the MKE-themed T-shirts.
What is the most surprising thing about living in Milwaukee?
As a frugal person, I'm still impressed by how cheap things are in Milwaukee, compared to places like Chicago or even Madison.
What’s something about Milwaukee that people always get wrong?
Most people have a very stereotypical view of the city from old shows like Laverne & Shirley or Happy Days (yes we have a Bronze Fonz, and yes we make fun of it), but there is so much more depth and excitement here than people assume, and I enjoy making readers love Milwaukee just as much as I do.
What's something new or changing about the city that you're most looking forward to in 2020?
The DNC! It's going to be crazy busy that week and I can't wait to identify places and neighborhoods that will appear on TV.
Number one can’t-miss recommendation for a visitor?
If you're looking to ingest the most Milwaukee thing you can, stop at Kopp's for a butter burger and frozen custard, or just head to any bar and order a brandy old fashioned sweet. A Friday night fish fry doesn't hurt, either.
Number one piece of advice for a first-time visitor?
Forget all the stereotypes you might have and meet some locals at the nearest bar.
What's your ultimate bucket list destination you've always wanted to visit?
Believe it or not, I still have to visit New York City, just so I can eat my way through. I have simple needs.