13 Milwaukee date night itineraries for every kind of couple

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A night out on the town should be nothing but fun, but whether it’s a first date or quality time with your favorite person, planning the perfect date night can be stressful. 

What do you do? Where do you go? How many activities should you plan for your evening? While the answer is unique for everyone, we put together a few ideas for every type of couple. 

Are you a fun-loving festival couple that loves to discover unique flavors and enjoy incredible outings? Or maybe you crave the chance to be creative and do some hands-on creating together before relaxing with a delicious dinner. Spend some time in the “Cream City” and take in all it has to offer and have a great time with your partner.

No matter what it includes, your vision for Milwaukee date night is likely full of fun, exciting, memorable places and space for date night. So let us unload some of the stress by helping you plan an incredible night out.

The adventurous couple

If quality time with your partner looks like an adventure out and about, there’s no shortage of activities you can plan for your date night. 

Head to an escape room & spy-themed dinner

Choose from four different themed room options at Escape The Room. For 60 minutes, you and your partner will search for clues and problem-solve to get out of the room before the countdown ends. The rooms can accommodate a minimum of eight players per scenario, making this activity great for a double date.

You can celebrate your escape with a visit to Safehouse Milwaukee, where you can continue your exciting adventure with a spy-themed dining experience. 

Photo courtesy of Escape the Room Milwaukee via Facebook.

Go Axe Throwing

If you’re looking for adventure and some snacks for date night, take a swing (or rather, throw) with an ax-throwing experience at Axe MKE.  Make sure you reserve ahead — while they can accommodate walk-ins when there is space, it’s first come, first serve. If you enjoy a more relaxed scene, head to Hooligans Sports Bar, a few minutes walk from your axe-throwing adventure. 

Hit the water in a kayak

This activity is perfect for couples who want to get out and on the water — and bonus, no need to be a kayaking pro. Brew City offers kayak rentals for exploring on your own, or if you prefer a little guidance, check out their guided tours. Choose from several experiences including sunrise, sunset, skyline, and even one that includes cheese curds (of course), and more.

Replenish your energy after your adventure by visiting one of many lakefront restaurants. We love the Blue Bat Kitchen for dinner or Sweet Diner for breakfast, brunch, or lunch. 

Photo courtesy of Brew City Kayak via Facebook.

The foodie couple

Spending an afternoon and evening out and about calls for a few snacks along the way. But if you don’t want to incorporate snack packing into your plans, make food experiences part of your date.

Take a cooking class

It’s one thing to go out for a single delicious meal on date night, but taking your date out to a place where you can learn to cook your favorite dishes together again and again is the experience that keeps on giving.

Check out classes at spaces like Braise for a variety of dishes like Cajun Shrimp Etouffee and Vegetarian Chile Relleno. Or, for classic favorite dishes like Classic Calzones, Birria Tacos with Elote, or Legendary Eggrolls, book a class at Gloriosos Italian Market

Photo courtesy of Glorioso’s Italian Market via Facebook.

Visit The Milwaukee Public Market

Why is The Milwaukee Public Market a foodie couple fan-favorite? It’s a year-round foodie heaven that houses up to 24 unique food vendors with everything from burgers and meats to sweet treats. There’s a variety of flavors for everyone to enjoy.

If you want a calmer, more intimate environment, take your dinner to go and relax by the lakefront. The mrket also offers a few cooking classes and mixology experiences if you’re interested in getting hands-on. 

Embark on a food and drink tour

Whether you want to go on a stroll or for a drive, spend some quality time with your partner while you get to know Milwaukee through your favorite foods and drinks. Enjoy a ton of different tour options that range from drinks and dessert to snacks and lunch — check out Milwaukee Food & City Tour’s calendar to book yours today. 

Photo courtesy of Milwaukee Food & City Tours via Facebook.

The creative couple

Enjoy a creative take on date night. Regardless of what medium speaks most to you and your partner, there are countless opportunities to create or consume unique works of art.

Paint and sip

If you want to relax and paint on date night, consider a class where you can create and enjoy your favorite drinks with your favorite person. It’s a perfect activity for any creative couple to appreciate, and the unique art you create together commemorates the memorable experience.

Consider the Farmhouse Paint & Sip Bar to dip your toes (and brushes) into painting. Keep your creative flow going by taking a short drive to La Merenda for dinner. The building is a renovated woodworking shop with an incredible outdoor patio you’re sure to enjoy. They even have a garden (on the property) where they source some of their ingredients from.

Photo courtesy of The Farmhouse Paint Bar & Banquet Hall via Facebook.

Wander the MKE Art Museum

The Milwaukee Art Museum is one of a kind and the perfect place for a creative couple to go on a date. Exploring the museum’s iconic architecture is only one reason you’ll love this space. Not only does the museum feature incredible collections, but occasionally, there are tours and other events on the grounds.

Once you’ve had your fill of a unique art experience, it’s time to fill up on a delicious meal downtown. Since you’re already nestled in the area, there are plenty of places nearby including the Oak Barrel Public House, The Knick, and more.

Take a candle pouring class

Many creative couples have tried classic classes like paint and sips, but have you ever tried a candle pouring class? A venue like the Glassnote Candle Bar is a great place to try it out. Choose your favorite scents and create your own candle as a couple to use at home and remind you of this great date night.

After you finish pouring your candles, allow someone else to pour you a good drink with dinner at the Odd Duck or O’Lydia’s Bar and Grill

Photo courtesy of Glassnote Candle Bar via Facebook.

The photo-op couple

If you want to capture the magical moments from date night, there are plenty of places to check out that offer incredible scenery and fun experiences. 

Stroll through the Third Ward

Not only is the Historical Third Ward known for being home to unique and delicious food in the Milwaukee Public Market, but it also has scenic riverwalks that are the picture-perfect location for an impromptu photo shoot.

Once you’re done with your photo-op there is no shortage of incredible (and picturesque) places for dinner, including The Wicked Hop, Tre Rivali, and more.

Delight in The Domes

Calling flower lovers and photographers everywhere! If you appreciate the beautiful backgrounds, the Mitchell Park Horticultural Conservatory provides the perfect place for a photo-filled date night. In addition to seasonal displays, you can always find a desert, tropical, and floral dome. Later, review your highlight reel from your visit during dinner at the Milwaukee Brat House nearby. 

Photo courtesy of Mitchell Park Domes via Facebook.

Check out North Point Lighthouse

The North Point Lighthouse is a gorgeous location to take a few photos with your sweetheart, but it also doubles as a museum. Explore the breathtaking scenery and learn about the lighthouse’s history going back to 1855. Continue your Insta-worthy date night by visiting Bartoloattat’s Lake Park Bistro for a fine dining experience. Or, if you’re looking for something more casual, consider a spot that pizza lovers rave about, like Ian’s Pizza

The festival couple

Regardless of what season date night falls in, there are always festivals going on in Milwaukee


Even when there’s blustery cold outside it doesn’t stop festival season in Milwaukee. From ‘Dry’ January and the Ice Bear Fest to a Bacon Fest in February, Shamrock Shuffle in March, and plenty of flower festivals across Wisconsin, there’s a festival for date night any time of the year. Most festivals include specialty foods and drinks specific to the theme.

Photo courtesy of Shamrock Shuffle via Facebook.


By the time we get the warmer weather in Wisconsin festival season is in full swing! There is every sort of fest you could want to explore on date night. You’ll have a chance to try lots of fun food during events like German Fest, Polish Fest, Bastille Days, and more.

And, of course, we’d be remiss to not mention Milwaukee hosts the world’s largest musical festival, Summerfest, where you can catch live music from your favorite artists and bands. 

Fall & Winter

Even though cooler breezes blow in the festival scene is year-round in Milwaukee! Starting off in September, there are a few wine fests and autumnal gatherings. And as home to one of the largest populations of German descent, it wouldn’t be October without a couple of Oktoberfests to enjoy. Even amid holiday celebrations, you can take a night off from the impending holiday chaos and enjoy a holiday light festival with your special someone.

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  • Holly Garcia

    A freelance writer who is passionate about education, mental health, parenting, and all the lifestyle things in between, Holly is a lifelong Southeastern Wisconsinite. She regularly contributes to several lifestyle and parenting publications.

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