The short version: Start at Prospect, drift west past the Italian grocers, see the Oriental Theatre and Black Cat Alley, then walk up Lake Park and down to Bradford Beach. Eat at Glorioso's and Zaffiro's. Stay at The Pfister.
In 2005, barely out of the closet, I opened Babylon, a Thursday gay night at the old Trocadero on Brady Street. We hit capacity the first night.
Twenty years later I sit on the board of Brady's business district and I'm still queering up the street. Brady has been Milwaukee's Little Italy, its hippie strip and its late-night hangout, and you can feel all three on one walk.
Where to walk on Brady Street and the East SideBrady Street. Start at Prospect and drift west toward the river. Italian grocers, corner bars, all in a few blocks. Look up: the second floors tell the story. Visit Brady.
Black Cat Alley. A back alley behind the Oriental turned outdoor gallery, between Kenilworth and Ivanhoe. Five minutes to walk through, an hour if you take photos. Black Cat Alley.
The Oriental Theatre. A 1927 movie palace at 2230 N Farwell Ave, run by Milwaukee Film. Buy a ticket for the lobby alone. Oriental Theatre.
Lake Park and Bradford Beach. Olmsted's firm designed the park: stone bridges over wooded ravines and the North Point Lighthouse up top. Take the stairs down to Bradford Beach and walk Lake Michigan, then climb back up for dinner. Lake Park.
Landmark Lanes. Old-school bowling under the Oriental's block, with a bar and an arcade. The rainy-night plan everyone ends up loving. Landmark Lanes.
Where to eat on Brady StreetPick up a deli sandwich and the olive bar at Glorioso's and carry it to Lake Park. Get cannoli filled to order at Peter Sciortino's Bakery and eat them on the sidewalk. For cracker-thin Milwaukee pizza in a room that hasn't changed, go to Zaffiro's and get the sausage. Coffee with big windows: Rochambo. A liter of beer at Von Trier.
Open late and feeling like a college kid again: Pizza Shuttle at 1827 N Farwell Ave. Nobody has to know.
Where to stayI'd book The Pfister Hotel. Coming from Chicago, take the Amtrak Hiawatha and skip the car, then ride The Hop streetcar.
Want a weekend like this?I'll plan yours. Tell me where and when, and I build the plan day by day and book it with you. Request a trip or book a Creative Burn.