Everything retro is new again, including the realm of cocktails. Sweet ice cream-based drinks that were popular, and sometimes created, in the 1960s and ’70s are making a comeback in Milwaukee. A number of bars and restaurants serve them, not just the usual supper clubs. Here are 10 spots to grab a creamy liquid dessert.
At Random
2501 S. Delaware Ave.
414-481-8030
Though rumors of its closure or sale have been circulating for years, At Random is still chugging along in Bay View, though the hours are still seemingly…at random. It’s still dark and romantic, with a good dose of Frank Sinatra playing in the background. Flip through the large-font cocktail menu, or just ask the bartender for whatever ice cream drink is their favorite lately. No matter what you get, it’ll be delicious and topped with a cookie around the straw.
Black Sheep
216 S. Second St.
414-223-0903
This Black Sheep doesn’t have any wool, but it’s got a sophisticated spiked shake (and a whole lot of wine, but you’re not here for the wine today). They keep it simple, using Purple Door salted caramel ice cream blended with Jameson whisky. It’s a subtle, rich combination made with premium ingredients that doesn’t need anything else to make it shine. Any minimalist drinker would love this one.
Bryant’s Cocktail Lounge
1579 S. Ninth St.
414-383-2620
No list of ice cream cocktails could be complete without Bryant’s, possibly the oldest cocktail lounge in Milwaukee. It has a storied spot in cocktail history—including ice cream concoctions—some of which were invented here. The Pink Squirrel is made with vanilla ice cream, crème de cacao and crème de noyaux, a red almond-flavored liqueur made with apricot pits. The Blue Tail Fly, also invented here, gets its bright color and light orange flavor from blue curacao, while the Banshee gets its flavor from banana liqueur.
Five O’Clock Steakhouse
2416 W. State St.
414-342-3553
Five O’Clock Steakhouse has everything you’d ever want in a supper club: relish trays, vinyl tablecloths with paper placemats and year-round twinkling Christmas lights. It’s the perfect atmosphere to sit at the bar and sip an ice cream cocktail. The usual classics are represented on the menu, including Grasshoppers and Brandy Alexanders, along with all three of the ice cream drinks invented at Bryant’s (Banshee, Blue Tail Fly and Pink Squirrel). It’s an extra bit of local history in a supper club that’s been around since the 1940s.
Joey Gerard’s
5601 Broad St.
414-858-1900
There’s no better spot to enjoy an ice cream cocktail than at a retro-inspired supper club. Joey Gerard’s in Greendale serves up five different versions at the bar. There’s the standard Grasshopper and Pink Squirrel, but it’s the Pal Joey that you should order. It’s a mix of Kahlua, Bailey’s, amaretto, crème de cacao, ice cream and the not-so-secret ingredient, mascarpone cheese. It’s thick and super rich thanks to the cheese. If you don’t think you’ll have room for it after a prime rib dinner, order it first.
Merriment Social
240 E. Pittsburgh Ave.
414-645-0240
Ever since Merriment Social has increased its menu focus on burgers, the selection of shakes has grown as well. These beauties are over-the-top, massive creations of candy, sauce, cookies and anything else you can think of. Try the Caught in the Rain, which includes pineapple rum, coconut milk and vanilla ice cream with coconut crumble and pineapple around the rim. The other four shakes on offer are non-alcoholic, but a shot can be added for an additional fee. They are: Hot Fudge, Salted Caramel, Calamansi Creamsicle and Chocolate Peanut Butter.
Point Burger Bar
10950 W. Good Hope Road; 414-797-2970
W229 N1400 Westwood Drive, Pewaukee; 262-955-9192
Nothing goes better with a burger and fries than a milkshake, and Point Burger Bar knows that. They also know that adults like shakes, so there’s a menu of a dozen different booze-filled variations. The Frosted Gingerbread is great for fall with vanilla, gingerbread and hazelnut flavors. A chai tea adult shake includes brewed chai, vanilla, Malibu coconut rum and vodka whipped cream. Dreamsicle, salted caramel, peppermint and raspberry cheesecake are just some of the other flavor combos.
Stack’d
170 S. First St.
414-273-7800
Stack’d is another burger bar that does alcoholic shakes right. You can order any of their standard shakes “spiked” with various liquors. Two of your options are made with Sprecher sodas: a vanilla shake with cream soda and spiked with vanilla vodka and a Dreamsicle made with orange soda and spiked with citrus rum. There are also chocolate, strawberry and Grasshopper versions. Furthermore, there are occasionally spiked shake specials made with infused liquors and local ice cream, so keep an eye out for those.
Supper
1962 N. Prospect Ave.
414-509-6074
Supper has branded itself as a modern supper club, and you can get great versions of classics like Grasshoppers and Brandy Alexanders. But there’s also a section on the cocktail menu called “Modern Ice Cream Drinks,” and that’s where the unique drinks are. The Kentucky Mudpuppy is a not-too-sweet blend of caramel pretzel ice cream, bourbon and Central Waters Mudpuppy Porter—all topped with whipped cream and a chocolate-covered pretzel rod for good measure.
The Knick
1030 E. Juneau Ave.
414-272-0011
The Knick does something that is unusual around here, but is quite common in a lot of old-school supper clubs around the state: Their ice cream drinks are served in a martini glass and are thick enough that there’s a six-inch tower of smooth drink piled above the rim of the glass. It’s a sight to behold, but you better move those spoons quick. Grab a classic or order something like the Godiva at the Knick, made with Godiva chocolate liqueur and Chambord for a raspberry boost.
