35 Amazing Winter Date Ideas Milwaukee | Date Night In Milwaukee
Is it the middle of winter, and you struggle to find that ideal date idea? No need to worry. Having lived in Wisconsin all our lives, we’ve been in your shoes. We’ve compiled this list of Amazing Winter Date Ideas Milwaukee, that we love and are sure you will also.
We have personally enjoyed almost all of these winter date ideas and highly recommend them. They are on our Milwaukee Bucket List if we haven’t enjoyed them yet.
Just because it’s winter, that’s no excuse to hibernate and not enjoy a night out with your partner. Date nights are key to a healthy and happy relationship.
Milwaukee is one of Wisconsin’s oldest and largest cities. It’s also the city with so much to do. Couples find Milwaukee a city filled with amazing opportunities for winter date nights.
With these 35 Winter Date Ideas in Milwaukee, you will have no trouble finding someplace romantic to spend an evening out.
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Date Night In Milwaukee
Date nights are an extremely important part of all intimate relationships. There is no excuse for not making dating a priority. Milwaukee’s cold winter is no excuse for staying home, especially when Milwaukee is full of so many romantic things to do on a date.
Ice Skating at Slice of Ice
Bundle up and head outdoors for this date night in Milwaukee. This date will have you strapping on your skates and enjoying time together at Milwaukee’s largest outdoor ice skating rink, Slice of Ice Skating Rink.
Fun fact ~ The Slice of Ice Skating Rink is larger than the ice rink at Rockefeller Center in New York City.
Your romantic date night at Slice of Ice will take you to the heart of Milwaukee’s downtown in Red Arrow Park. The facility has a skate shop with rentals if you don’t have your own.
No need to worry if you need to warm up. A warming house and a nearby Starbucks have just what you need to top off your date.
Depending on the weather, the rink is open from December through February and sometimes into March.
Address ~ 920 N. Water St., Milwaukee
Iconic Bowling at the Holler House
Located in Milwaukee’s historic Polish south side and hidden below a century-old, family-owned, landmark tavern the Holler House is the oldest certified bowling alley in the United States.
There’s no fancy seating in this bowling alley, the charm is old-school original. The two lanes are located in the basement and are still the original old rickety wood floor. The pins are still set by pin setters, who are usually neighborhood kids. And get ready to keep your score on paper.
Bowling is only by reservation and only when pin setters are available. What a fun winter date idea this will be in Milwaukee.
This small family-owned tavern is filled with over 115 years of stories. After bowling be sure to stay awhile and enjoy the charm of this hidden gem. Check out the history represented in the decor and photos of celebrities that have visited Holler House, sample the menu, and talk with the locals.
Check out more of this iconic Milwaukee landmark on Instagram.
Address ~ 2042 W. Lincoln Ave. Milwaukee
Wine and Chocolate Pairing at Indulgence Chocolatiers
Experience a fun and different way to enjoy chocolate. Pairing is when you use different flavors to complement or balance out the counterpart.
Learning to complement chocolate with the right wine, beer or mixed drink makes for a very educational and fun date.
At Indulgence Chocolatiers Walker Point location, you can stop in and enjoy a chocolate pairing anytime during regular hours, by ordering off their regular menu.
For more formal learning about pairing chocolates with wine or food, you can attend an after-hours class given by the owner of Indulgence Chocolatiers. Reservations are required.
We recommend that while you are visiting Indulgence Chocolatiers you wander down the street to Morels and enjoy their farm-to-table comfort food, prepared with elegance.
Address ~ 211 S. 2nd. Street, Milwaukee
Make Candles at Glassnote Candle Bar
The scent is everything. What could be more romantic than walking into a scent bar knowing you are going to create your fragrance together? At Glass Note Candle Bar that’s exactly what you can do.
Make a reservation for an evening to enjoy the fragrances. Work together to find that perfect blend that when you light your candle, it is relaxing and sets the mood for the perfect evening, while also reminding you of intimate moments together.
Address ~ 524 S. 2nd St. Fl. 2, Walkers Point Neighborhood, Milwaukee
Light Show at the Domes
“There will be no winter blues or ho-hum dates when you take your sweetie to The Domes. The official name is Mitchell Park Horticultural Conservatory, better known as””The Domes” by locals, are living museum homes for plants from all over the country.”There will be no winter blues or ho-hum dates when you take your sweetie to The Domes. The official name is Mitchell Park Horticultural Conservatory, better known as “The Domes” by locals, are living museum homes for plants from all over the country.
Even on the coldest winter days, it’s warm and toasty inside all three of The Domes. The dessert, tropical, and floral domes all stay toasty warm.
On Thursday nights in the winter, light shows occur inside the domes. The light shows are set to music, and the shape of The Domes makes you feel as if the lights are surrounding you. The only other place I have seen a light show like at The Domes, was when we visited St Louis Union Station.
Address ~ 524 S. Layton Blvd. Milwaukee
Dinner and a Show
Enjoy an evening consisting of dinner and a show. The arts are a huge part of Milwaukee’s DNA. Several theaters can be found throughout Milwaukee’s cultural district.
For a special date idea in Milwaukee during the cold winter months, start your evening with dinner at the Stackner Cabaret followed by a live performance by the Milwaukee Rep.
The Stackner Cabaret Restaurant is open to the public before and after performances and will take dessert and drink orders during intermission.
It’s the perfect place for a romantic meal before your evening entertainment.
You can see the current schedule of performances and purchase tickets at the Milwaukee Rep.
Address ~ 108 E Wells St., Milwaukee
Ice Bar at BelAir Cantina
Experience specialty drinks, food, and beautiful ice sculptures on a 20-foot ice bar when you and your date visit The Ice Bar at BelAir Cantina.
This year BelAir Cantina Ice Bar returns to the corners of Brookfield and BelAir Cantina in Tosa.
To make your winter date in Milwaukee extra special, you can reserve a VIP experience in a heated booth, including a blanket to cuddle under.
Address ~ 20111 W. Bluemound Rd., Brookfield 250 High Street, Brookfield
Enjoy Coffee at Colectivo Coffee
Colectivo Coffee is a fun place for a winter date. Stop in and enjoy a sampling of coffee drinks and food. Then sit a while and have an evening or afternoon of good conversation while you are seated at either the indoor fireplace or the outdoor firepit.
Colectivo Coffee serves hand-roasted coffee, coffee drinks, lattes, cappuccinos, teas, and a wide selection of pastries and sandwiches.
Colectivo Coffee also has free wifi, you can bring your computer and start planning out your next Wisconsin Road Trip.
Address ~ Corner of 68th & Wells St., Wauwatosa
Afternoon Tea at the Pfister
Not all dates need to take place at night. For a one-of-a-kind experience, make a reservation for two, to enjoy afternoon tea at the Historic Pfister Hotel.
Afternoon tea takes place on the 23rd floor of the Pfister Hotel. You will enjoy an elegant experience while being surrounded by a panoramic view of Milwaukee and Lake Michigan.
Your relaxing afternoon of elegance can only be enhanced by adding Victorian finger foods and desserts. Reservations are required.
Address ~ 424 E. Wisconsin Ave, Milwaukee
Sign Up for a Couples Dance Class at Fred Astaire
Have you wanted to learn to dance? Or do you want to get in step with your partner or learn something new together? Fred Astaire Dance Studios instructors will have you finding your passion for dance.
This romantic activity is a fun and engaging way to exercise with your partner or perfect your dance skills for a special occasion.
If you are looking to learn the Salsa, the Samba or just improve your ballroom dancing, sign up for dance lessons and use your date time to escape the cold and step inside Fred Astaire to be inspired.
Address ~ 625 E Saint Paul Ave., Suite 100, Milwaukee
Cooking Class at Glorioso’s
For something unique make a reservation for a cooking class at Glorioso’s Shop. This winter date night is sure to leave a lasting impression. On your date, you will not only go out to eat but learn to prepare the meal yourselves.
This culinary adventure date is ideal for a couple who wants to learn to cook or perfect their talents in the kitchen.
Cooking together is romantic and a learning adventure as you learn new cooking techniques and get to see the culinary side of your partner.
Address ~ 1011 E. Bradley Street, Milwaukee
Rent a Hut At Zocalo Food Park
Make a reservation to rent a winter hut at Milwaukee’s only food truck park. There is no need to stay home just to stay warm.
The heated huts at Zocalos Food Truck Park are a fun place for a romantic date. Each hut is heated and cozy. You will have your own personal server. With a variety of food trucks to order from, you can have a true smorgasbord to choose from.
Heated huts can be reserved for 90 minutes. You can make a reservation for a Zocala Hut ~ HERE.
Prior to your meal, you may want to reserve a pre-dinner Sauna session at Hot Spell Sauna.
Address ~ 636 S. 6th Street, Milwaukee
Enjoy Live Music at Blu Bar and Lounge
Treat your date to an evening of drinks, music, and elegance at Blu Bar and Lounge. This elegant lounge on the 23rd floor of the Historic Pfister Hotel is where not only the best martinis are served but local jazz singers perform.
Blu Bar has been awarded Best Martini/Romantic Bar, Best Place for Date Night, and Best Hotel Bar. I would nominate Blu Bar as having the best panoramic view of Milwaukee.
On Friday and Saturday evenings, you can enjoy live music performances from 7 pm to 11 pm.
The elegance, ambiance, drinks, and breathtaking city view equal a night filled with romance.
Address ~ 424 E. Wisconsin Ave, Milwaukee
Tour Great Lakes Distillery
There are so many winter date ideas for Milwaukee, but when coming up with fun ideas don’t forget that the city of Milwaukee is known as the beer capital of the world. This means there are some amazing distilleries that you can visit and tour.
Great Lakes Distillery is the first distillery to open in Milwaukee after prohibition. They have produced award-winning spirits.
Great Lakes Distillery today still uses traditional methods and is excited to offer tours to show you the process they believe in.
During your date, you can take a one-hour tour and learn about the history of the distillery, and the process they use to produce their award-winning spirits. Your tour will end with a full tasting of their spirits. If you are not a drinker they will have alternatives.
Reservations are highly encouraged and you can purchase tickets online.
Address ~ 616 W Virginia St., Milwaukee
Cedarburg Winterfest
As Wisconsinites, we learn to embrace the cold. So why stay indoors when you and your date can enjoy the annual Cedarberg Winter Festival which takes place in February?
Each year the festival takes on a different theme, the 2023 theme is the Wild West.
“Activities throughout the two-day festival include an Ice Carving Contest, barrel races, Cedarburg’s famous “costumed bed-races on ice,” camel rides, outdoor activities and so much more, including a romantic Saturday night, Battle of the Bands Hoedown Showdown.”Activities throughout the two-day festival include an Ice Carving Contest, barrel races, Cedarburg’s famous “costumed bed-races on ice,” camel rides, outdoor activities and so much more, including a romantic Saturday night, Battle of the Bands Hoedown Showdown.
Address ~ Downtown historic Cedarburg
Ice Castles Lake Geneva
If you want to create a date that is filled with awe and wonder, visit Wisconsin Ice Castles.
A visit to Wisconsin Ice Castles in Lake Geneva is a magical, romantic, and chilly winter date idea. This magical fairytale is an experience that visitors can only have in a few select cities each year.
Bundle up, and don’t forget your boots and mittens. You will be walking around on the ice.
The goal of Ice Castles is the create happiness made of ice. After visiting you will see that they not only hit their goal but went way beyond. The memories and smiles of your date together at Ice Castles will live on and continue to put smiles on your face long after you leave.
Address ~ 1091 Hidden Cottage Cir., Lake Geneva
Milwaukee Public Market
A trip to the Milwaukee Public Market together makes for an ideal daytime or early evening date. When making a trip to this amazing indoor market you will find a variety of permanent vendors selling an array of food, local fresh produce, coffee bars, a specialty bakery, a wine bar, and cooked-to-order food.
Balcony seating is available for those wanting to hang out and people-watch while you are eating your lunch.
Address ~ 400 Water Street, Milwaukee
Visit the Harley Davidson Museum
Walk through the history of Harley Davidson with a date at the Harley-Davidson Museum. This is a fun date, enjoy the journey of the vision of two young men and see what a dream can become. Check out our date night visit to the Harley-Davidson Museum, Milwaukee.
On display throughout the museum are various Harley-Davidson memorabilia motorcycles, including one of the very first motorcycles built by Harley-Davidson. Relive some of your favorite movies and tv shows and see some of the motorcycles featured in films.
“Following your tour of the museum, you can pick up matching t-shirts or one-of-a-kind souvenirs in the gift shop and enjoy a burger and a drink at””Motor” their onsite restaurant. “Following your tour of the museum, you can pick up matching t-shirts or one-of-a-kind souvenirs in the gift shop and enjoy a burger and a drink at “Motor” their onsite restaurant.
Extra ~ If you are a true Harley-Davidson fan, you won’t want to miss the 4-day Harley-Davidson, 120th-year celebration, which takes place on July 13th – 16th, right in the heart of Milwaukee.
Address ~ 400 W. Canal St., Milwaukee
Skip the Line and buy tickets to the Harley-Davidson Museum online.
Tour the Pabst Mansion
Step back in time and feel the romance when you tour the Pabst Mansion and relive the story of Captain Pabst and how his love brought him to Milwaukee.
Enjoy the amazing architecture of the Pabst Mansion and feel the love that once filled the rooms of this stately Victorian mansion. Your docent will take you on a tour of the home and share with you the history of the home, the Pabst family, and why it’s significant in Milwaukee’s history.
We toured the Pabst Mansion on our romantic trip to Milwaukee and fell in love with everything about the Pabst family.
Address ~ 2000 W. Wisconsin Ave, Milwaukee
Pamper Yourselves at WELL Spa
Continue to enjoy the romance and elegance of the Pfister with a trip to the Pfisters WELL Spa and Salon. Whether it’s a visit for a manicure or pedicure, the trained professional at Pfister Spa will have you feeling relaxed and pampered.
For a little something extra, book a couples massage and enjoy total relaxation.
Following your pampering together, top your evening off with a nightcap in the Pfister Lounge or visit the hotel’s artist-in-residence and enjoy the extensive art collection displayed throughout the Pfister Hotel.
Axe Mke
Get out your flannel shirts. With this date idea, you’re sure to hit the bullseye. At Axe Mke, your evening date will be filled with fun, exercise, and a little competition.
Axe Mke has 12 lanes and can accommodate up to 6 people per lane. If a date night with friends is what you are looking for this might make for a fun evening. Reservations are suggested but if you like to live on the wild side they do try to accommodate walk-ins.
If no lanes are available, guests are encouraged to sit at the bar, enjoy some drinks and watch some axe throwing.
Reservations are for 90 minutes of throw time. Once you have checked in, your evening at Axe Milwaukee will start a 10-minute safety demonstration. From there the remainder of your 90 minutes can be spent throwing.
Axe throwing is hard work be sure to order drinks and food from their menu to stay hydrated and energized.
Address ~ 1924 E Kenilworth Place, Milwaukee
Adventure Rock
Climbing can be an activity for everyone, especially when it’s done safely inside. This is a great opportunity to take your date to a higher level.
Whether you are a beginner or a seasoned climber this indoor rock climbing center has a climbing wall that almost anyone can attempt. With a wide selection of walls in a variety of ability levels you and your date can have an enjoyable time at Adventure Rock.
With your day pass to Adventure Rock you can also participate in yoga and fitness classes.
Address ~ 2220 N. Commerce Street, Milwaukee &
613 S. 2nd St., Milwaukee
Roller Skate at Incredi-Roll
Have a fun night at Incredi-Roll roller skating and playing arcade games at this retro skating rink.
This indoor rink is warm and toasty, but that doesn’t mean you can’t hold hands while skating.
Although this skating rink is in West Allis, 20 minutes from Central Milwaukee it is worth the drive to spend a nostalgic evening together with your sweetie.
Address ~ 10928 W Oklahoma Ave, West Allis
Bryant Cocktail Lounge
Take your date to Milwaukee’s oldest cocktail lounge. Bryants has been a Milwaukee fixture since 1938. Once you visit you’ll know why. It’s the place you visit and don’t want to leave.
When walking in the door the vintage tunes, velvet wallpaper, and exotic lighting set the stage for what awaits you.
At Bryant’s Cocktail Lounge, you and your date can cozy up in a booth while you sip on a signature drink made just for you.
Bryant’s does not have a drink menu, you let them know your likes and your dislikes and they will mix a drink that they believe fits your taste. If you do have a favorite signature cocktail, they can craft that too.
Our suggestion is to just let them surprise you and craft you something special.
Address ~ 1579 S 9th Street, Milwaukee
Breakfast at Sweet Diner
Why not start your date off on the right foot? You can’t lose when you head for Sweet Diner to start your date with breakfast and coffee.
Located in Milwaukee’s Third Ward this trendy place is very popular. Make sure to get an early start and avoid the wait. If you get a table by the window you can enjoy each other’s company and watch the foot traffic.
In addition to its coffee bar, Sweet Diner only serves breakfast and lunch. What they do they do well. Not only are the meals delicious but they are served in a very eye-appealing way.
Following breakfast, take a winter walk and check out Milwaukee’s Third Ward, one of the most iconic warehouse districts in the country.
Milwaukee’s Third Ward is an artsy neighborhood with lots to offer. In addition to the culture you’ll find boutiques and one-of-a-kind home and fashion shops
Address ~ 239 E Chicago St. #103 Milwaukee
Solve a Mystery at Dinner Detective
Saturday date night can involve a little mystery as you and your date attempt to solve a hilarious murder.
The Dinner Detective is the ideal setting for an exceptional four-course dinner. But we caution you, the night’s killer is somewhere in the room and may even be seated right next to you. Or could it be your date?
This evening of mystery is unlike any other. There are no costumed actors and no stage. The characters could be seating right next to you and you could find yourselves a prime suspect or the main detective.
This intriguing night of mystery takes place on Saturday nights at the Hyatt Regency, Milwaukee. Advance tickets are required and can be Purchased Here.
Address ~ 333 W Kilbourn Ave., Milwaukee
Build Your Own Mini Golf
Nine Below is a one-of-a-kind build your our mini-golf bar.
At Nine Below you will head nine feet underground and build your own mini golf course.
Your date night will look a little like this, make your two hour reservation, then after you arrive you will be assigned an empty green. You will work together, using Nine Below’s obstacles. Your mini golf course is your own design and challenge.
Once your golf course is built, grab your golf clubs, the challenge is on. A little healthy and friendly competition is good for relationships.
Address ~ 1905 Ze. North Ave., Milwaukee
Visit Milwaukee Art Museum
Milwaukee is a city filled with history and culture. With this date you can enjoy both history and culture in one place.
Milwaukee is home to several museums that would make the ideal setting for an afternoon date. The Milwaukee Art Museum is a favorite among couples. So why not take an afternoon and stroll through the museum together?
This museum date is a good time to walk around and see what each other’s artistic taste and flavors are.
You may also want to check their schedule, some of the museums have free admission days.
Painting with a Twist
Let’s do something creative and fun and rekindle that spontaneity! Plan a date night with your partner that takes place at Painting with a Twist.
Even if you have never picked up a paintbrush before, this evening of fun will have you both feeling creative and like an artist.
Can you picture the both of you sipping wine, giggling, and trying to follow instructions to create the masterpiece that will hang on your wall to remind you of your evening together?
Address ~ 155 E. Silver Spring Drive #201 Whitefish Bay
Escape the Cold at a Tiki Bar
If you are dreaming of warm weather, beaches, and umbrellas in your drinks. Then take your date to one of Milwaukee’s famous tiki bar.
At Foundation Bar you can enjoy an evening filled with Polynesian culture while sipping one of their famous Mai Tais or other tropical drinks. Their ambiance has excellent decor, authentic music,and great drinks all give Foundation Bar and authentic wicked Tiki Vibe.
Address ~ 2718 N Bremen St. Milwaukee
Hotel Staycation
Have dinner at one of Milwaukee’s downtown restaurants and then book a night at one of Milwaukee’s beautiful hotels.
Your hotel staycation is the ideal way to fend off those winter blues that might set in. This date might take your date to a new level.
Booking.comEnjoy a Comedy Show
This date will have you enjoying a show at Milwaukee’s home for stand-up comedians.
The Laughing Tap has featured national headliners and only the best of quality local comics.
There is no minimum drink order for the evening. Their bar features many of the local craft beers, cocktails, and wine. If you are not a drinker, they do have alternatives.
Address ~ 706 B South 5th St, Milwaukee
Take a Tour With City Tour MKE
Take your date on a tour of Milwaukee. While traveling with a guide in a five-seater electric vehicle. You’ll explore the history of Milwaukee, visit some of the most popular tourist destinations and some of Milwaukee’s hidden gems.
As you travel, your guide will fill you in on Milwaukee’s exciting and sometimes seedy history. Even full-time residents of Milwaukee have discovered a side of Milwaukee they have not seen before.
Game Show Battle
If a group date is on your radar Game Show Battle Room in Milwaukee is where you want to head.
Get ready for one of the most fun evenings of your winter, as you battle it out as contestants on your very own game show. This evening will have you facing off against your friends in a hilarious and challenging way.
This brand new game show experience is something everyone can enjoy. What a great team-building activity this is for any couple.
Catch a Bucks Game
If there is a sports enthusiast among you, then it’s time to bust out your Milwaukee Bucks shirts and cheer on Milwaukee’s home team.
Fiserv Forum is home to Milwaukee’s very own Bucks, a World Champion Basketball team. There’s plenty to cheer about when enjoying a basketball game together. When the game is over you’ll find plenty of places to eat nearby.
Address ~ 1111 Vel R Phillips Ave., Milwaukee
Our Conclusion
Milwaukee is an exciting city that is filled with many romantic date ideas. Finding winter date ideas in Milwaukee is not difficult. This Wisconsin city does not disappoint. If you are looking for winter indoor or outdoor activities, you can find something in Milwaukee.
Winter is no excuse to put your dating life on hold even in this cold northern state.
More Milwaukee Fun
- Dinner, Dining, and Nightlife in Milwaukee’s Historic Third Ward
- See what awaits you behind the Harley-Davidson Museum Doors
- Exploring the Historic Pfister Hotel Downtown Milwaukee
- Romantic Things to see and do in Milwaukee
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