10 Winter Date Night Ideas Around Milwaukee (2022)

Winter is upon us, and the urge to hibernate is real.

But there are some good reasons to go out and about with your partner this season.

Milwaukee is full of extra-romantic things to do in the winter, and date nights can help to keep your connection strong amid life’s craziness.

Go on, call the babysitter.


10 Winter Date Ideas in Milwaukee

1. Rent a Winter Chalet at South Shore Terrace.

Snuggle up with s’mores and a view of Lake Michigan!

Private winter chalets are returning to South Shore Terrace this year, starting November 25th and running through January 28th. Each chalet rental accommodates 2-6 people, a food and beverage credit, and Lake Michigan views.

Reservations can be made at www.southshoreterrace.com


2. Visit the Magic Forest at At Random.

The Magic Forest holiday pop-up is back at At Random in Milwaukee’s Bay View neighborhood.

Festival drinks and hot cocktails will be served on their decorated patio. You can reserve a heated cocktail hut or brave the cold by the fire pit.

Inside, transport yourself back to 1964 with a visit to this iconic cocktail lounge, with its low lights, comfortable seating, and vintage decor. Money can’t buy you love, as the Beatles sang, but it can buy you a Love Bowl.

Snuggle into a dark booth and share a massive “Love Bowl”, or choose from a large menu of mid-century ice cream drinks and classic cocktails. It’s the perfect place for romance.


3. Eat dinner in a Lux Dome at Cafe Benelux.

The iconic heated domes are back this year at Benelux Cafe and Cafe Hollander locations around Milwaukee.

Reservations are now available for heated and private winter experiences in domes, globes and ice fishing shanties for groups of 6-8 at each of the groups’ eight restaurants in the Milwaukee area and Madison.   

The most high-end option is the $150 Lux Domes reservation at Cafe Benelux.

It includes a private Lux Dome for 90 minutes for 6-8 guests, two beverage packages, a keepsake Lux Dome camp mug for everyone in your party, and more food platter and beverage packages.

Café Benelux is located in the Historic Third Ward at 346 N Broadway.

Reservations for the Dome Villages at Cafe Hollander are $50 and include 90 minutes and seating for up to six people, plus 2 drink packages of your choice.

Café Hollander has four Milwaukee area locations:

Milwaukee, Historic Downer Avenue neighborhood at 2608 N Downer Ave 
Brookfield, The Corners of Brookfield at 20150 Union St 
Mequon at 5900 W Mequon Rd.
Wauwatosa Village at 7677 W State St 


4. Watch a Light Show at the Domes.

The first light show of the year at the Mitchell Park Domes will be on Friday, November 25th.

After that, all light shows will be on ‘Late Night Thursdays, with admission extended to 8pm (last admission is one hour before close) on Thursday nights. Here is a preview from last year:


5. Go on a Sleigh Ride.

It’s lovely weather for a sleigh ride in southeastern Wisconsin!

Take a magical sleigh or sled ride in the great outdoors. There are local options at Apple Holler, Dan Patch Stables, Roden Barnyard Adventures, and more.

See the options for sleigh rides >>


6. Cozy Up in an Ice Shanty

Frank & Larry’s Northwoods Shanties are back at Cafe Hollander.

At Cafe Hollander in Wauwatosa, Frank & Larry’s Northwoods Shanties are back for outdoor winter dining, handcrafted by KMS Limited in Eagle River.

$100 reservations include 90 minutes in the private, heated shanty, seating for 6-8 people, and two beverage packages.


7. Enjoy Live Music at Blu Bar & Lounge.

Watch the snow fall from the rooftop of the grand Pfister Hotel. You may as well be a million miles away from diaper changes and school pick-up lines.

Pop a chilled bottle of champagne and be swept away with live music on Friday and Saturday nights. The view of the city is unbeatable.


8. Make a Candle Together at Glassnote Candle Bar.

From jasmine to lavender, and blue lotus to sandalwood, certain scents play a key role in love and romance.

At Glassnote Candle Bar, you can explore these scents together and incorporate them into a special keepsake candle. The experience lasts for two hours or more, and they also offer a drink menu. It’s a unique date idea for people who like to try new things.


9. Go Ice Skating at Milwaukee’s “Rockefeller Center”.

The Slice of Ice ice skating rink in Red Arrow Park is in the heart of the city, and the rink is actually bigger than the one at Rockefeller Center in New York City. (That’s a fact!)

The urban surroundings are upbeat and exciting, and the park is decorated with festive holiday lights in the wintertime. Popular music is amplified outside, which makes the environment even more fun and energized.

Warm up together in the Starbuck Warming House, where you can rent and return your skates, sip on hot cocoa, and play footsies by the crackling fireplace.

Across the street at the Marcus Center for the Performing Arts, you can catch a Broadway show like “Les Miserable” or “Six”. Check out the 2022-23 schedule here.


10. Catch a Bucks Game at Fiserv Forum

Bust out your Bucks gear and cheer on your World Champion team at the Fiserv Forum. There are plenty of places to eat and drink nearby or onsite.


Related: 25 Romantic Things to do in Milwaukee

Do have more romantic ideas? What are more fun things to do as a couple in Milwaukee? Email us at hello@mkewithkids.com.

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