Get there in time for the fleeting warm nights of summer. But even on cooler nights, heat lamps, blankets and fireplace tables make it a supremely cozy spot. The rooftop is actually partially enclosed so it stays open all year round.
“As an upscale rooftop bar in the Historic Third Ward, we’re always seeking new ways to enhance our guest experience,” says General Manager Joe Adamczak. “Since Milwaukee sees such a short window of summer weather, the new outdoor bar provides additional bar seating and service in the sun as well as an oversized television so guests can enjoy the weather and full view of the city skyline while catching up on their favorite local sports teams.”
The Outsider’s summer cocktail menu is still going strong with Frosé, Pineapple Daiquiri, and my pick, the Jamaican Whiteclaw with rum, grapefruit and almond-orange flower syrup, topped with Topo Chico. There is also full food menu if you want to dine al fresco or plenty of savory and satiating bar snacks if you stop in for happy hour. I sampled the deviled eggs with truffle oil and bacon-wrapped dates while relaxing in a cushy lounge chair and both were bite-size flavor bombs I’d order again (and again).
And if you’ve decided you overindulged a bit too much on the rooftop, stumble right downstairs and check yourself into the Journeyman Hotel. Thoughtful details like yoga mats and dry bar hair styling tools in the rooms, pints of Jeni’s ice cream delivered to your door and Milwaukee-made leather backpacks available to use for exploring the city make it a truly unique boutique hotel. It’s the perfect spot for a planned stay-cation, too.
The Outsider opens at 4 p.m. every day and only accepts reservations for large groups. The best time to beat the crowd is before 6 p.m. on Saturdays and Sundays or early in the week on a Monday or Tuesday. And because of Milwaukee’s unpredictable weather, the outdoor bar may not be open every day, so be sure to call ahead if you have your heart set on it.
