From Milwaukee’s Third Ward out to the western ‘burbs there are a few choice spots to book a table between May and October. Make sure to bring your sunglasses and your smartphone because you are going to want to take snaps of the view, whether the sun is cresting into the horizon or it’s a new-to-you glimpse of Milwaukee at high noon.
Things turn Tiki when you zip up the elevator to the 9th floor at The Journeyman Hotel. Yes, you can sip an Oaxacan Exchange (mezcal with lime, orange-peppercorn and pink sea-salt mist) but some of the food skews tropical, too, with mini tuna tartare cones and frozen push-pops in flavors like Orange Creamsicle. Bonus: indoor and outdoor spaces are compatible with fussy weather, but if it’s sunny out, definitely grab a spot in a sectional sofa within the L-shaped outdoor space. You’ve never seen this view of Lake Michigan before, trust us.
You can see a lot from a second-story roof in the Third Ward, it turns out. Café Benelux’s rooftop space is open for lunch and dinner—as well as weekend brunch—on warm-weather days. Umbrellas over each table shield you from the sun. With a menu modeled after Belgium’s cafes, signature dishes include cheese-stuffed bitterballen, mussels with frites or gulden draak pecan pie, plus a hearty roster of sandwiches, salads and burgers.
The second floor of Ugly’s Pub opens onto a rooftop patio with birds-eye views of Old World Third Street. Enjoy rooftop happy hour specials after work or a live DJ at night. The patio is outfitted in comfy lounge seating and tables, and there’s plenty of standing room as well. Dress to impress — this scene is anything but Ugly.
Named for its seventh-floor perch at the top of Hotel Metro, many people still don’t know about this cozy gem. One reason is that it’s now only available for private events (in other words, if you score an invite, go!). Plants and a mini garden add color and the feeling like you’re at your cool cousin’s pad in Brooklyn, while a fireplace (both indoors and out) staves off any cool weather. Walls of windows ensure the view of downtown-Milwaukee’s skyline is never compromised.
It was a sad day when the original Pizza Man location on East North Avenue burned to the ground in 2010—but pizza-loving palates rejoiced when owner Mike Amidzich announced he was reopening in a new spot. At the Downer Avenue eatery—there are two other Pizza Man restaurants, in Oak Creek and Wauwatosa—is a glass-enclosed rooftop with a retractable roof to snap shut on cooler days or during inclement weather. But cross your fingers for sun and you’ll have the pleasure of eating pizza above Downer Avenue.
For years, Taylor’s has been a popular East Town bar. In 2009 its owners opened this little sibling in downtown Waukesha. Earlier this month the rooftop opened for the season, with beers on tap and the same menu that’s served downstairs for lunch, dinner and weekend brunch (Crème Brûlée French Toast is among the delicacies). For a group, this is a great place to meet as the culinary offerings are varied, from a brat burger on a pretzel bun to four entrée-sized salads (including “Rosie’s Garden,” greens tossed in balsamic-raspberry vinaigrette), and will easily satisfy picky palates.
On the 13th floor of this membership-based club on North Broadway in downtown Milwaukee is a rooftop lounge open for private member events only–such as the recent Kentucky Derby party. Members have access to the rooftop and it’s also available for weddings and other events surrounding the Big Day. With exposed-brick walls and twinkling white lights, it’s a cute little spot in the downtown corridor.