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.

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