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Milwaukee bars with special holiday cocktails

Holiday cocktails
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Holiday cocktails with orange, rosemary, star anise, and cinnamon.

The holiday season has looked a bit different this year, as the relatively warm weather has made the city look less like a winter wonderland than it usually would. But if you’re hoping to get into the holiday spirit there are plenty of places to go in the city and get a nice seasonal cocktail.

Lori Fredrich, the dining editor of On Milwaukee and a regular Lake Effect contributor, shares her picks for the best bars to grab a holiday cocktail.

1. At Random

This classic Milwaukee bar may be well-known for its ice cream cocktails and moody interior, but during the holidays it boasts an outdoor winter wonderland on its patio. It's called the Magic Forest and has heated huts where you can enjoy a cocktail, with hot and cold options alongside its famous ice cream specialties.

"If the theory that drinking hot things in the summer cools you down or eating hot food, spicy food cools you down, maybe drinking ice cream drinks in the winter warms you up," says Fredrich.

2. Bryant's

For fans of specialty crafted cocktails, it may come as no surprise that Bryant's is one of the best places in Milwaukee to grab special holiday drinks.

Fredrich says, "They have a classic punch that has been served [since] way, way, way back in history... every year they have a ceremonial tasting."

Aside from the punch, Bryant's is also one of a few bars in the city that makes its own Tom & Jerry batter. In fact, Fredrich says it has a room dedicated to the classic Christmas cocktail.

"You can always be assured of finding a warm drink there, whether it's an Irish coffee or something more interesting. [Von Trier]"

3. Von Trier

Like Bryant's, Von Trier is one of just a few Milwaukee bars that makes its own Tom & Jerry batter. It also has an extensive list of hot cocktails, perfect for warming up a cold evening.

"You can always be assured of finding a warm drink there, whether it's an Irish coffee or something more interesting. I'm pretty a lot of [them] they've made up themselves," says Fredrich.

4. Elsa's On The Park

Although Elsa's may be more known for their martinis, Fredrich says this east side restaurant also makes a great hot buttered rum. And aside from the drinks, guests can come to see holiday decor with an impact.

Fredrich explains, "Every year they do a Christmas tree that is created by an artist. Sometimes it's a political statement, sometimes it's simply an artistic statement on the world."

5. Pufferfish's Sippin' Santa Pop-up

Getting to this tiki lounge at the top of Hotel Metro can be challenging, but once there, guests are treated to a tropical oasis in the heart of downtown Milwaukee. While that might not sound Christmasy, per se, Fredrich says the bar hosts a unique holiday pop-up that fits both the tiki and holiday aesthetic.

The Sippin' Santa pop-up bar is a nationwide project that works with bars in different cities to host the pop-up and donate some of the money earned to charity.

"[It's] kind of like if you envision Santa trading out his sleigh for a surfboard, that's sort of the vibe," says Fredrich.

6. Lost Whale's Elf Pop-up

The film Elf turns 20 this year, and to celebrate you could head to Lost Whale in Bay View.

"Lost Whale has done this theme for a few years and every year it gets just a little bit better. Every drink is named after a scene in the movie and they've pretty much... picked up on every reference to food in the movie and somehow incorporated it in as an element in a cocktail," says Fredrich.

Does that mean there's a cocktail with maple syrup and spaghetti? Yes, but don't worry: there isn't real pasta. "I believe the spaghetti takes the form of red licorice whips," Fredrich explains.

7. Tin Window's Miracle Pop-up

The Miracle pop-up is a nationwide project, where bars celebrate the season with decorations, charity donations, and seasonal cocktails. Tin Windowis already a cozy bar in Milwaukee's Walker's Point neighborhood, but Fredrich says the Miracle pop-up cranks it up a notch farther.

"Definitely expect over-the-top decor. The Miracle pop-ups always have really great, Christmasy cocktails, so you get all of those different spice blends that remind you of the holidays," she says.

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Joy is a WUWM host and producer for Lake Effect.