The short version: Stay downtown or on the East Side, walk everywhere you can, ride the streetcar for the rest, and pick one chapter below to start. Come in fall for the trails, in summer for the ballpark, any time for Brady Street.
I live in Milwaukee, I sit on the board of a business district here, and I'll meet you for coffee. This is the guide I'd give a friend who texted, "We're coming to Milwaukee. What do we do?" Each chapter below is its own guide, so start where your trip starts.
Pick your Milwaukee* [Brady Street](/blog/brady-street-milwaukee-walking-guide). The East Side's old Little Italy, still weird. Italian grocers, Black Cat Alley, a 1927 movie palace and a walk down to the lake.
* [A Sunday walk downtown](/blog/sunday-walk-milwaukee-bluff-art-museum). Ten stops on foot from Ogden and Prospect to a bar seat at The Vig, then the streetcar home.
* [Fall in Milwaukee](/blog/fall-in-milwaukee-guide). Hikes, river trails, candlelight walks and Halloween on Brady.
* [Baseball in Milwaukee](/blog/baseball-in-milwaukee-guide). Where to stay, how to reach the ballpark and where to eat after the game.
* [Neighborhoods, queer, loud or quiet](/blog/milwaukee-neighborhoods-guide). Find the part of town that fits you.
* [Milwaukee's Scars](/blog/milwaukee-walking-guide-for-people-who-notice-things). A walk for people who notice what a city leaves behind.
* [Forced Perspective](/blog/forced-perspective-milwaukee-walk). A walk along the freeway that never reached the lake.
Where to stay in MilwaukeeMilwaukee doesn't have many hotel rooms, so book early on game weekends and festival weekends.
* The Pfister Hotel: downtown's historic grand hotel, close to the lakefront and the theatre district.
* Kimpton Journeyman: the historic Third Ward, walkable, with a rooftop bar.
* Saint Kate, The Arts Hotel: downtown, with art on every floor.
* Drury Plaza Hotel Milwaukee Downtown: reliable, and kind to a budget.
* The Plaza Hotel: the East Side pick, near Brady Street.
If rooms run out, stay in Chicago and take the Amtrak Hiawatha north. It's about ninety minutes, and you skip the car.
Getting around MilwaukeeDowntown and the East Side are walkable. The Hop streetcar covers the stretch between the Third Ward, downtown and the lakefront. For the trails and state parks, rent a car for the day.
Want this planned for you?Tell me where you're headed and when, and I'll plan Milwaukee day by day and book it with you. Free to ask.
Request a trip or book a Creative Burn.