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Food & Drink Neighborhoods & Living Things To Do

16 Winter Date Night Ideas in Milwaukee

Just because it’s winter doesn’t mean your dating life needs to freeze!! There is an abundance of things to do in and around Milwaukee that make the perfect activity for couples (newly dating or 10+ years married).

So, thaw your calendar, grab your partner, and pick one of these 16 ideas as your next date night.

Candlemaking at Glassnote
Design your signature scent from over 100 fragrances at this vibey candle and cocktail spot.

Paint & Sip at Splash Studio
Embrace your inner Leonardo da Vinci by painting your own masterpiece while sipping on your favorite drink.

Take a Class at the Milwaukee Public Market
Painting, cooking, cocktail making, and more classes can all be found at everyone’s favorite Public Market.

Stone Creek Coffee Factory Tour
For only $8, you’ll tour the green storage area, roasting facility, cupping lab, learning lab, and their bakery. There will also be plenty of free coffee, some bakery treats to taste and a signature glass to take home.

Comedy at The Laughing Tap
Enjoy a care-free night laughing alongside (or at) local and national comedic acts at The Laughing Tap. If you’re feeling really brave, they have open mic nights on Wednesday.

Jazz at Caroline’s
Relax and soak in the world-class jazz that Caroline’s has to offer. This is the perfect spot to hit for insanely good music, great cocktails, and the ultimate late-night vibe.

Trivia Night at Local Gems
From Camp Bar and Ope! to Blüm and Lakefront Brewery, there are plenty of spots to test your and your partners’ knowledge.

Distillery Tours
Warm up with a buzz that only bourbon or whiskey can provide at distilleries like Great Lakes or Twisted Path.

Casino Night at Potawatomi
Whether you’re a seasoned bettor or slots newbie, Potawatomi is a fun place for couples to go if they enjoy the rush that comes with the winnings (if you’re lucky).

Milwaukee Sports Night
Milwaukee Bucks, Admirals, UW-Panthers, and the Milwaukee Wave all make great events to cheer on local sports teams together.

Glow Tubing at Crystal Ridge
Fly over snow-covered lanes under colored lights for an unforgettable couple’s night out.

Head Massages at Luna Lu Herbal Head Spa
Find your zen together while enjoying the one-of-a-kind head massages that only Luna Lu offers.

Afternoon Tea or Cocktails + Jazz at Blu
The Pfister Hotel offers plentiful options for winter date activities. Grab afternoon tea or listen to jazz while sipping on cocktails in the Blu martini lounge.

Enjoy a Fancy Dinner at the Harbor House
Splurge and treat each other to a seafood-lover’s dream dinner at The Harbor House while you overlook a chilly-looking Lake Michigan.

A Weekend at Sand Valley
Speaking of splurge, instead of just a date night, why don’t you make it a whole weekend? There’s no better spot to do that than at Sand Valley where you can ice fish, enjoy great meals, hike, bike, and more! An adventurous couple’s dream getaway!

Staycation at Dubbel Dutch with Cocktails at Agency
Embrace the winter vibes and plan a staycation at a local hotel like the Dubbel Dutch. BONUS: Its first-floor bar, Agency, is an award-winning hybrid bar for unique cocktails and mocktails.