Image of Milwaukee Art Museum in Winter with snow covered ground around it

12 Things To Do in Milwaukee in Winter: A Local Couple’s Favorites

By: Craig

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When those cold winter months in Milwaukee feel like they are never going away, there is no better time than to get out and explore Milwaukee.

How do we know? We’ve lived in Milwaukee for over 15 years and have felt our share of cabin fever in the winter.

Whether you are a local looking to survive the winter or a visitor to our wonderful city, we have a list of winter activities that will help you enjoy your time in Milwaukee during the winter.

Things to Do in Milwaukee in Winter

Attend a “Secret” Concert

Are you looking for a unique musical treat in Milwaukee this winter? Sofar Sounds is the answer.

It’s not your typical concert. It’s intimate, hosted in unconventional venues like small coffee shops and breweries.

The artists are often local gems, just waiting to be discovered. And the audience is small, so every performance feels personal. 

And the best part! You don’t know where the venue is until 36 hours before the show!

We did one of these and loved it! We ended up at a brewery where they were closed to the public for the night. 

Milwaukee’s Sofar is a perfect way to spend a Milwaukee winter night. 

Bust Some Stuff

Smashing a beer bottle with a sledge hammer at Bust-n-Stuff in Milwaukee WI
Smashing a beer bottle with a sledge hammer at Bust-n-Stuff in Milwaukee WI

Feeling a bit tense lately? Maybe a bit fed up with work or just everyday life?

Well, I’ve got just the thing for you in Milwaukee: Bust-N-Stuff! It’s this awesome spot in the Lincoln Warehouse, right in the heart of the Bay View Neighborhood.

Here’s the deal: you get to suit up in coveralls, gloves, and a face shield, and then… well, you get to smash stuff! It’s a safe, fun way to release all that pent-up energy.

Just a heads-up, you’ll need to book an appointment. But the cool part? Your group gets the whole place to yourselves. It’s an absolute blast and definitely not your everyday activity. Trust me, you’ve got to try it out!

Enjoy a Tea Party at The Pfister

Afternoon Tea at The Pfister Hotel is an experience that takes you back to a more elegant era. Held on Friday, Saturday, and Sunday afternoons, this is an experience you’ll remember. 

The Pfister Hotel isn’t just any hotel. It’s an icon. It’s a Milwaukee tradition. And Afternoon Tea? It’s an experience to savor.

Imagine this. A tableside tea blending, presented in gleaming silver service. A Pfister Tea Butler at your service. You’ll learn about each tea variety’s origins, unique flavors, and health benefits. You’ll even discover the art of blending and pairing teas.

And the food? Oh, the food! Fresh scones, dainty sandwiches, delicate pastries. Your taste buds are in for a treat. They even have gluten-free options upon request. 

Here’s the catch. It’s a summer-only affair. So, check their website for booking info.

Afternoon Tea at The Pfister Hotel, it’s not just tea. It’s an experience. A memory you’ll treasure. A very Milwaukee-esque memory.

Create Your Own Letterpress Poster

Craving creativity this winter in Milwaukee? Bay View Printing Co has something special for you.

Welcome to Drink & Ink Nights. For just $35, you can explore the world of letterpress printing. Make your own 11×17 poster with antique wood type, paper, and ink.

And here’s the fun part: you can bring your own snacks and beverages. Enjoy them while you create!

These sessions run most Thursdays from 6-9 PM. Only ten guests at a time, so it feels personal and cozy.

Bay View’s Drink & Ink classes perfectly escape the usual winter routine. Check their calendar and book fast because spots fill up. Here’s to a crafty winter night in Milwaukee!

Escape Winter at a Tiki Bar

Craving a tropical escape from Milwaukee’s frigid winter air? The city’s Tiki Bars are your passport to a faraway land right in the heart of Wisconsin.

Tucked away in the Riverwest Neighborhood, Foundation is a festive haunt with Polynesian decor and a playful vibe. Tropical drinks, an ample rum list, and island charm make it a perfect winter hideaway.

Up on the rooftop of Hotel Metro, you’ll find Pufferfish. It’s more than a bar; it’s a throwback to a time forgotten, where the drinks flow easily and time stops.

Trader Nick’s in Cudahy flaunts pirate flags and beckons you into a Polynesian/Caribbean paradise. Cudahy’s first and only tiki bar, it’s a hidden gem for those seeking winter warmth.

And then there’s The Palapa at St Paul’s Fish Market in the Historic Third Ward. Here, tiki meets seafood, resulting in a culinary and sensory delight. And you’ll find some of the city’s most friendly and fun bartenders. 

Milwaukee’s Tiki Bars aren’t just places to drink; they’re escapes, experiences, and tropical antidotes to a Wisconsin winter. Slip into a Hawaiian shirt, order a Mai Tai, and let Milwaukee whisk you to a sunny shore. Aloha, winter!

Play Shuffleboard 

Indoor shuffleboard in Milwaukee brings a fresh twist to winter fun. Two spots stand out for those looking to enjoy this engaging game without braving the cold, whether you’re an expert or a beginner.

First up is the Northsouth Club. It’s not just a place to play; it’s a social hub. With shuffleboard courts that beckon, you’ll immerse yourself in the game and the lively atmosphere. You can also test your arm with some axe throwing. 

Then there’s the 3rd Street Market Hall. It’s a market, it’s dining, and yes, it’s shuffleboard. You can engage in a game or two between bites of delicious local fare. It’s casual and fun and adds a playful note to your winter dining experience.

These two venues turn shuffleboard into more than a game. It’s a Milwaukee winter experience that combines sport, socializing, and a sprinkle of local flavor. 

Take a Brewery Tour

Image of a "cheers" on the Lakefront Brewery Tour in Milwaukee, WI
Image courtesy of Lakefront Brewery

Brewery tours in Milwaukee are a must, and winter is no exception. The city’s rich beer heritage comes alive in these tours, offering insights, flavors, and stories that go beyond the ordinary pint.

Lakefront Brewery is a local favorite, renowned for its engaging tours that blend humor, history, and beer tasting. Whether you’re a craft beer aficionado or new to the brew, Lakefront’s welcoming atmosphere is a delight.

Miller is another legendary name, offering tours that take you through the heart of one of America’s most iconic breweries. Walk through the vast brewing halls and witness the art and science behind a household name.

For a unique twist, consider the Beer History Tour at Best Place. This isn’t just about tasting; it’s a journey through time, exploring the heritage and evolution of Milwaukee’s beer industry.

These tours are more than a way to escape the cold; they celebrate Milwaukee’s brewing legacy. From hops to history, they provide a flavorful way to experience the city in winter.

Go Bowling

Milwaukee’s bowling tradition goes deep, especially during winter. This isn’t just a pastime; it’s woven into the very fabric of the city’s culture. From classic lanes that resonate with history to quirky twists on the game, there’s something for every enthusiast.

Falcon Bowl in Riverwest has been rolling since 1920, offering a taste of Milwaukee’s rich bowling heritage. If retro vibes are more your style, Landmark Lanes in East Side serves up a vintage feel that’s a perfect strike.

For a unique twist, don’t miss Koz’s Mini Bowl. It’s mini bowling, and it’s a blast. Imagine all the fun of traditional bowling but with smaller balls, shorter lanes, and human pinsetters. It’s a different game altogether.

With these options, bowling in Milwaukee becomes more than a winter activity; it’s a way to connect with the city’s soul. Whether you’re seeking nostalgia or novelty, Milwaukee’s lanes are calling.

Learn About Milwaukee by Taking a Tour

Image of Milwaukee City Tour by the Bronz Fonz
Image courtesy of Untapped Tours

Milwaukee in winter is a landscape waiting to be explored, and what better way to discover its charm than through guided Milwaukee tours

These tours offer something unique, perfect for locals wanting to see a familiar place with fresh eyes and visitors eager to soak in the city’s rich culture and history.

The Historic Milwaukee’s Skywaukee Tour brings a new perspective to downtown exploration. An indoor tour guides you through the skywalk system, unveiling significant landmarks one story up. This is a warm, intriguing, and unique winter exploration at its finest.

Untapped Tours goes a step further, hopping you onto a bus and whisking you around Milwaukee’s treasures. Over two hours, your guide, passionate about the city, paints a vivid picture of Milwaukee’s culture and history. It’s educational, entertaining, and genuinely local. Visitors adore it, and locals (including me) can’t recommend it enough!

These tours aren’t just about sightseeing. They’re journeys into the heart of Milwaukee, sharing stories, secrets, and the warmth of a city that embraces winter with open arms. Whether on foot or on wheels, touring Milwaukee is a winter adventure not to be missed.

People Watch at the Public Market

Image of vendors at Milwaukee Public Market. Image is taken from above and looks down on the vendors

The Milwaukee Public Market is one of our favorite places to escape to in the chilly winter months. And one of my favorite things to do at the Market is people-watch! 

Start with a glass of wine at Thief Wine Bar. The atmosphere is chic, the wines are exquisite, and the people-watching opportunities are prime. It’s a perfect perch for observing the market’s bustling rhythm.

Next, indulge your sweet tooth. Whether it’s a scoop of creamy ice cream or a piece of decadent chocolate, the market has treats to warm your heart on a chilly day. Savor and watch; the market’s colorful crowd never disappoints.

And don’t forget to take a piece of Wisconsin home with you. Stock up on favorites like cheese curds and brats. They’re the flavors of Milwaukee, and they’re waiting for you at the market.

Take a Cooking Class

Milwaukee Public Market hosts a variety of classes, from sushi rolling to gourmet cupcakes. It’s a culinary playground for chefs and food lovers alike.

Braise Culinary School offers a farm-to-table experience, focusing on local ingredients and seasonal recipes. It’s perfect for those who want to connect with Wisconsin’s rich agricultural roots.

Sur La Table at Bayshore Town Center has classes for all skill levels. Whether you’re a kitchen novice or a seasoned home cook, there’s something to stir your culinary creativity.

And if you are a Milwaukee resident, check out the Milwaukee Rec Department for their reasonably priced cooking classes. 

Ice Skate at Red Arrow Park

Red Arrow Park is the place to be for outdoor ice skating in Milwaukee.

It’s more than just skating. It’s a Milwaukee winter tradition. Right in the heart of downtown, the park transforms into a winter wonderland.

Strap on those skates and glide through the crisp winter air. Whether you’re a pro or just finding your balance, it’s all about enjoying Milwaukee in winter.