Food & Drink

Where to Get Milwaukee's Best Boozy Milkshakes, From Classics to Originals

Published On 08/02/2016 Published On 08/02/2016
Boozy milkshakes Milwaukee
Lacey Muszynski/Thrillist
Lacey Muszynski/Thrillist

Joey Gerard's


After you devour your French onion soup, cheese curds, and giant steak, you'll probably want to sip your dessert leisurely at the bar. While you can never go wrong with a Grasshopper or Pink Squirrel, it's the Pal Joey that should be on your radar. This concoction blends Kahlua, Bailey's, amaretto, creme de cacao, and mascarpone cheese with vanilla ice cream for something like a tiramisu in a glass. A sprinkle of freshly grated nutmeg lends a fragrant punch of spice.

At Random

Bay View

This beloved bastion of Tiki drinks and ice cream cocktails closed recently while searching for a new owner, and although no one has stepped up to buy the business yet, this classic joint quietly reopened its doors last month -- so get in there while you still can. Everything here is a throwback, and we suspect the lights are red to keep people from noticing that the space is as dingy inside as it looks outside. However, Milwaukeeans are not the sort who get deterred by a dive, so we still happily belly up to this old-school bar for whatever crazy ice cream concoction the team can whip up... complete with a cookie hanging around the straw.

Lacey Muszynski/Thrillist

Point Burger Bar

Park Place

There are a DOZEN spiked shakes to choose from on the menu at Point Burger Bar. You'll have a hard time deciding between the Campfire Smores and Salted Caramel Brittle, so take one for the team and just order a flight of shakes. That's right: you can get five little glasses of boozy ice cream, so you'll never have to make a decision that difficult again. There are some unique flavors on offer here, from chai tea with coconut rum to macadamia nut with Kahlua.



Like all good supper clubs, Supper offers a large selection of boozed-up shakes, though joints like these tend to prefer the more refined moniker "after-dinner drinks." You can order up classics like the Brandy Alexander, but since Supper goes for a modern spin on the supper-club concept, consider trying one of the updated drinks, like the Space Travel, which combines Wisconsin's hyper-local Blue Moon ice cream with hazelnut liqueur.

Stack'd Burger Bar

Stack'd Burger Bar

Harbor View

Sure, you can get any of the shakes at Stack'd without alcohol. But why would you order something with "virgin" in the name? Two of the shakes incorporate local Sprecher soda for a blended float kind of deal: the orange dreamsicle combines Sprecher Orange Dream soda with vanilla ice cream and citrus rum for an extra-bright pop of flavor that'll take you on an adults-only trip down nostalgia alley. Some specials include local ingredients like Purple Door ice cream and house-infused liquor, so be on the lookout for those.

Courtesy of Black Sheep

Black Sheep

Walker's Point

Though it's really a wine bar, you can get a simple-but-tasty spiked shake at Black Sheep. It uses top-notch ingredients for a sophisticated beverage: a combination of Purple Door salted caramel ice cream and Jameson whiskey, which makes for a smooth, rich drink. You already passed up the roasted cauliflower for the burger, so you might as well just completely throw your diet out the window and drink up this rich dessert.

Bryant's Cocktail Lounge

Bryant's Cocktail Lounge

Historic Mitchell Street

Open since 1938, Bryant's is the quintessential cocktail lounge. The Pink Squirrel, a popular after-dinner ice cream drink at many supper clubs, was actually invented right here at Bryant's, so of course you should try that nutty, pink cocktail first. But if you're not quite sure what to try next, just ask the bartender for something with ice cream. They'll whip up an outstanding drink in no time flat, based on what you like. That's why this is truly a cocktail lounge -- there are no drink menus, because the bartenders are the drink menu.

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1. Joey Gerard's 5601 Broad St, Greendale, WI 53129

This may be one of the newer supper clubs in Wisconsin, but that doesn't stop it from being one of the best. Besides the usual steak dinners, you can enjoy tiki cocktails, veal picatta, and a multitiered lazy Susan filled with appetizers.

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2. At Random 2501 S Delaware Ave, Milwaukee, WI 53207

Sweet, creamy libations and boozy punch bowls are what's on offer at this Bay View 60s' era tiki bar and cocktail lounge. Serving naughty versions of old school soda fountain favorites (check out the booze filled Almond Joy milkshake), this spot specializes in ice-creamed based cocktails and seriously strong, fruity concoctions, all topped with the requisite tropical paper umbrella. Shiny banquettes, retro fixtures, and red mood lighting set the tone.

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3. Point Burger Bar 10950 W Good Hope Rd, Milwaukee, WI 53224

Specialty burgers and sandwiches shine at this new concept created by Stevens Point Brewery and the owner of Ward's House of Prime. Build your own burger from an extensive list of options to wash down with a boozy milkshake.

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4. Supper 1962 N Prospect Ave, Milwaukee, WI 53202

Get fancy at Supper, a New American style spot located in the Shorecrest Hotel. Inspired by the famous supper clubs of 1930s' Hollywood, Supper offers classic dishes like Oysters Rockefeller and Steak Delmonico with modern, gastronomic flourishes.

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5. Stack'd Burger Bar 170 S 1st St, Milwaukee, WI 53204

Beer and burger enthusiasts rejoice: with over 100 different beers to choose from and a “build-your-own-burger” menu of locally-sourced ingredients, this downtown spot is your new haven for bites and brews. Fifth Ward foodies can swing by the contemporary, industrial-chic Kramer Foundry Building to pick a meat that matches their mood -- maybe you’ll opt for free-range chicken, bison, or good ol’ grass-fed beef, while your vegan friend vacillates between black bean or chickpea walnut patties. If the endless options have you stressed, don’t worry: whatever you select is bound to be delicious as long as it’s served on a house pretzel bun.

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6. Black Sheep MKE 216 S 2nd St, Milwaukee, WI 53204

This hip wine bar and resto in Walker's Point offers a wide selection of craft vino on tap, plus chic bar fare. Working off flavors from traditional Wisconsin fare, the menu features elevated comfort food classics like fried chicken and eggs Benedict. Open for dinner and brunch, Black Sheep also hosts nightly wine happy hour.

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7. Bryant's Cocktail Lounge 1579 S 9th St, Milwaukee, WI 53204

A classic cocktail lounge, Bryant's serves expertly made Depression-Era cocktails -- like Old Fashioneds, Whiskey Rivers, and Cassis at bargain prices, particularly during its popular happy hour. If you're not versed in the cocktail trends of the 1930s, the bartenders here are remarkably unpretentious and friendly -- just tell them what you normally like and are in the mood for, and they'll take it from there. It all happens inside a dark and subtly posh corner bar -- old-school cool at a discount.