When the weather starts to get warm in Milwaukee—usually between Memorial Day and late October—the city's residents flock to the many alfresco dining and drinking spots. From a pretty living-room-like perch atop a Third Ward hotel to a craft brewery’s most casual “room,” several of Milwaukee’s bars and restaurants are taking over the roof giving great views of the city. These spaces are among the hottest reservations in town for imbibing and noshing.
When the Kimpton Journeyman hotel debuted in 2017 it rolled out the city’s highest-level rooftop space yet. Zip up the elevator to the seventh floor and order a cocktail (like “Violet Voodoo” with flavors of rosehip, lavender, and cardamom) or enjoy a sampling of dishes from the small-plates menu including comfort foods like fried cheese curds and blistered shishito peppers. The downstairs eatery, Tre Rivali, has "Top Chef" alum Heather Terhune at the helm serving up modern American fare with a Mediterranean twist. The Outsider’s glass walls and firepits cultivate cozy year-round (yes even in Milwaukee winters) and fun events include barbecue (Sunday) and shuffleboard. Being that this is Milwaukee, craft beer made in Wisconsin is on tap although oenophiles can appreciate California, French and Italian picks.
Modeled after a Netherlands or Luxembourg pub—your first clue is cheese-stuffed bitterballen on the menu not to mention all those hard-to-find Belgian beers—the second-floor dining space at Café Benelux lacks a roof, providing a bird’s-eye view of the Third Ward. In recent months the restaurant has also expanded patio seating to the parking lot and come winter, diners can book at table at one of six domes. They cant seat up to eight people and have special food and drink packages, A group of fussy eaters can easily find satisfaction here, from entrée-size salads to entrees such as roasted half-hen or six-spice rubbed salmon, plus burgers and sandwiches that make this a repeat meal for locals. The beer list is so thick, it’s dubbed a book and it shifts with the seasons, although the list is always a mix of Belgian and Wisconsin brews.
The Rooftop at Milwaukee Brewing Company
Located in the Arena District not far from the retrofitted Pabst Brewery complex, Milwaukee Brewing Company opened its new taproom (with 20-plus beers on tap) in a massive block-long building that plays host to a brewery, restaurant (Glass + Griddle), and rooftop restaurant aptly named The Rooftop in summer 2019. (Beer’s been made at Milwaukee Ale House, a gastropub in the Third Ward, since 1997.) Although the spacious patio out front may be tempting, for the rooftop you need to head upstairs where twinkly lights overhead show off the city skyline—and the innovative eats (like pizza dip, Korean fried chicken, and smoked street corn) are perfectly paired with beer.
Smack-dab on Old World Third Street in downtown Milwaukee is Red Star, which opened September 2019 inside the former Ugly’s Pub with a new look. Owned by veteran bar owner Michael Vitucci (also of Caffrey’s and Belmont Tavern), Red Star will take over the second and third-level alfresco spots and serve as a lounge and dance club, perfect if you want to dance in the open air. Another hot amenity: a gas-fired bar top where you can take a seat (and stay warm).
Good City Brewing
While this brewing company has two locations—the newest is next to Fiserv Forum in downtown Milwaukee—the first, open since 2016, is where beer is crafted. Skip past the ground-floor restaurant at Good City Brewing and take the stairs to the second-story roof where picnic tables and bar-height tables greet you. Continually voted some of Milwaukee’s best burgers (this is no small feat), patties on the menu bump up against farm-to-table finds like Pils mac ‘n cheese with Deer Creek aged white cheddar or Malaysian-style curry. On Thursday a buck from each beer sold—around 16 are typically on tap—goes to a local non-profit.
Punch Bowl Social
Calling itself “an amazing adult playground” with games like bocce, karaoke, bowling, a vintage arcade, a giant Jenga set, and shuffleboard, Milwaukee’s Punch Bowl Social in the Deer District includes a second-floor patio framing killer views of Fiserv Forum. If you get bored with the games (as if!), there’s much more to do here, like sipping brews in the outdoor beer garden or grabbing a meal (everything from healthy eats like superfood grain bowls to indulgent bites—like five-layer beef brisket chili).
Brother's Bar and Grill
With locations around the U.S., the Milwaukee one flaunts a second-floor uncovered patio overlooking Water Street, the city’s unofficial bar district. The feel is a mix of historic corner tavern and sports bar, with nightly specials on drinks and food and around 35 taps aimed at pleasing every beer drinker. Deals on drinks get even better if you bring in your very own Brothers Mug.