As winter settles in, Milwaukee offers an array of cozy, adventurous, and uniquely local date night options to warm your spirits and deepen your connection.
From fireside cocktails to festive lights, Milwaukee’s winter scene is packed with moments to make lasting memories.
So call the babysitter, make those reservations, and let the city charm you this winter!
1. Visit the Magic Forest at At Random.
The Magic Forest holiday pop-up is back at At Random in Milwaukee’s Bay View neighborhood, transforming this iconic cocktail lounge into a winter wonderland.
Sip festive drinks and hot cocktails on the decked-out patio, where you can reserve a heated cocktail hut for a cozy retreat or warm up by the fire pit for a classic winter experience.
Step inside and travel back to 1964 in At Random’s atmospheric lounge, with its dim lighting, plush seating, and vintage decor. As the Beatles once sang, “Money can’t buy you love”—but it can buy you a Love Bowl!
Settle into a secluded booth with your special someone to share this legendary oversized drink, or explore the full menu of mid-century ice cream cocktails and timeless classics.
2. Eat dinner in a Lux Dome at Cafe Benelux.
The heated domes have returned this winter at Café Benelux and Café Hollander locations across Milwaukee, offering private, heated spaces for groups of 6-8 to enjoy a winter dining experience. Reservations are now open for domes, globes, and ice-fishing shanties at any of their eight locations in Milwaukee and Madison.
Café Benelux in the Historic Third Ward offers a Lux Dome experience, which includes a private dome for 90 minutes with drink and food packages, as well as keepsake Lux Dome camp mugs for each guest. Café Benelux is located at 346 N Broadway.
Café Hollander locations also offer Dome Villages, available for groups of up to six for 90 minutes with optional drink packages. Café Hollander has four Milwaukee area locations:
- Milwaukee, Historic Downer Avenue – 2608 N Downer Ave
- Brookfield, The Corners of Brookfield – 20150 Union St
- Mequon – 5900 W Mequon Rd
- Wauwatosa Village – 7677 W State St
3. Dance the Night Away at MAM After Dark
The Milwaukee Art Museum’s beloved MAM After Dark is finally back, offering a perfect winter date night in a stunning, after-hours setting. Beginning on Friday, Jan. 24, this popular event series transforms the museum into a lively venue with music, drinks, light bites, and themed activities. The season kicks off with a “Salsa Night,” featuring live music from flamenco guitarist Evan Christian, performances by Mezclando Milwaukee, and a scavenger hunt celebrating Hispanic and Latinx artists. It’s a great way to explore the museum, dance, and enjoy a memorable night out with your special someone.
Tickets are $30 in advance or $35 at the door for non-members, and $10/$15 for members.
4. 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 >>
5. Cozy Up in an Ice Shanty
At Buckabatoon 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.
6. 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.
7. 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.
8. 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.
9. 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.
10. Ice Bar at BelAir Cantina (Brookfield)
The Corners of Brookfield and BelAir Cantina announced the return of the BelAir Cantina Ice Bar.
The 20 ft., 10,000-pound ice bar, featuring ice-carved photo opportunities, giant ice luges and specialty drinks, will also include a VIP experience where guests can reserve 90 minutes in a private heated booth, a complimentary drink package, blanket and more.
11. Watch a Light Show at the Domes.
Enjoy the beauty of The Domes after dark on select evenings!
- Dates:
- Fri, Nov 29, 9AM-8PM
- Tues, Dec 10, 9AM-8PM
- Tues, Dec 17, 9AM-8PM
- Fri, Dec 27, 9AM-8PM
- Admission: Included with regular admission; last entry is one hour before close.
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.
In 2013, Calie Herbst, a former teacher with three little ones, saw a need for a “One Stop Shop” for family fun in Milwaukee. So she founded Milwaukee With Kids. Her goal was to find the best this city has to offer families and share it with other parents. In one place.
In 2019, she published “Exploring Milwaukee WIth Kids”, a comprehensive Milwaukee travel guide for families and kids.
She appears regularly on WISN News, Fox 6’s ‘Real Milwaukee’, B93.3, and Wisconsin Morning News. She has been featured in Medium, the Milwaukee Journal Sentinel, NPR, the Wisconsin Jewish Chronicle, and on CBS 58 News.
Calie is available for hosting, moderating and media appearances.
