37 Fun Date Ideas in Milwaukee, WI in 2025

While grabbing a cocktail or taking a romantic walk are classic date activities, there are many other interesting date ideas in Milwaukee to keep your romantic outings fresh and interesting. There’s so much to do and see in this exciting city, so why settle on the same date night each time?

Whether you’re going on a brewery tour or exploring a botanical garden, you’ll never be bored exploring Milwaukee with your other half! To find out more about everything you can do together, read on for our favorite fun date ideas in Milwaukee.  

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• Foodie Date Ideas in Milwaukee
• Date Night Ideas in Milwaukee
• First Date Ideas in Milwaukee
• Winter Date Ideas in Milwaukee
• Indoor Date Ideas in Milwaukee
• Outdoor Date Ideas in Milwaukee
• Free and Cheap Date Ideas in Milwaukee

Foodie Date Ideas in Milwaukee

1. Create a Meal at a Cooking Class

Going out for a lovely restaurant dinner is great, but if you really want to impress your date, why not look into cooking classes in Milwaukee instead? When you and your date take cooking classes near you, you get to learn a new skill together and still get a (hopefully) delicious meal at the end of it. 

2. Enjoy a Private Chef Experience

There’s something that feels so upscale and luxurious about hiring a private chef instead of going out to eat. Private chefs in Milwaukee will gather all of the ingredients, do all of the prep work, cook your favorite meal and even handle the clean-up when they’re done. You and your date can sit back and relax while enjoying a delicious meal. Private chefs near you allow you to have a chef-quality meal from the comfort of your own kitchen — the ideal date idea if you want the sophistication of going to a fine dining eatery with the convenience of staying in.

3. Taste New Dishes on a Local Food Tour

Do you feel like you’ve eaten all of the good food in Milwaukee? Food tours in Milwaukee might be able to help. Local guides can take you and your date around town to spots you may have never been to before. Food tours near you can be fantastic for both long-time Milwaukee locals and people who are new to the city and want to get to know the area often called the Culinary Capital of the Midwest (yes, really). 

4. Take a Trip to the Milwaukee Public Market

Milwaukee couples who love food should visit the Milwaukee Public Market for diverse culinary delights. It prides itself on being the area’s most unique food destination, but you and your date can decide for yourselves if that’s the case. As you look around, you'll discover a variety of food vendors serving all kinds of sweet and savory cuisine.

5. Experience a Lake-View Dinner

Feel like going out for a lovely restaurant meal with a view? You and your date can enjoy a romantic dinner at Harbor House with lake views. Dine on fresh and delicious seafood while taking in stunning views of Lake Michigan and the skyline. This is a meal that’s best at sunset so you can truly appreciate the best view of the lake.

Date Night Ideas in Milwaukee

6. Listen to Some Jazz

Attending a live music show put on by the jazz enthusiasts at the Jazz Institute is a fun and unique yet laid-back date idea. The performances happen all over Milwaukee at various locations, so there’s always an opportunity for a jazzy date night! 

7. Go on a Brewery Tour

It’s clear that Wisconsin loves its beer. If you and your date also enjoy a good brew, take a brewery tour at one of Milwaukee's many craft breweries, such as Lakefront Brewery. You’ll learn all about the ins and outs of brewing delicious craft beers, and when the tour is done, you can enjoy a beer of your own. It’s a fun way to spend an evening and a perfect date idea in Milwaukee. 

8. Laugh at Stand-Up Comedy Together

Seeing stand-up comedy together is another great date idea in Milwaukee. There are many places to go, but we recommend starting with The Laughing Tap. From there, you can check out other popular stages where both local and touring comedians put on a show. If you and your date both love to laugh, this is a pretty foolproof date idea. 

9. Dare To Go On a Ghost Tour

Feeling spooky? This date idea in Milwaukee is perfect for that. Go on an eerie ghost tour with City Tours. You and your date will get to learn about the haunted history of Milwaukee and the spirits that may or may not still reside within the city. It’s a great way to get to know a bit more about the area. 

10. Treat Yourselves to a Romantic Dinner Cruise

If you’re looking for a highly romantic date night, go on a luxurious dinner cruise with a company like Edelweiss Boats. You’ll go out onto the inner harbor of Lake Michigan with a delicious meal that you can savor while watching the sunset with your date. 

First Date Ideas in Milwaukee

11. Catch a Milwaukee Brewers Baseball Game

Watching a Milwaukee Brewers baseball game is a classic and fun first date idea in Milwaukee for people of all ages. The lively atmosphere at American Family Field, the team's home stadium, adds to the excitement even if you’re not a big sports fan. Share some ballpark snacks, and cheer for the Brewers while you enjoy the company of your date. This is notably one of our top summer date ideas in the area.

12. Explore the Historic Third Ward

The Historic Third Ward is the creative hub of Milwaukee. Take a walk around and see what’s going on in this particularly artsy part of town. A relaxed stroll around the Historic Third Ward is the perfect first date idea in Milwaukee to get to know someone. If the date is going well, you can stop into one of the area’s many bars, restaurants or cafés to slow it down and talk further.

13. Picnic at Veterans Park

A picnic is an excellent first date idea in Milwaukee. Assemble a picnic basket and make your way to Veteran’s Park on the lakefront. It’s the perfect place to sit and chat while people-watching and getting some fresh air. 

14. Check Out the Brady Street Nightlife

A walk through Brady Street is another excellent way to spend a first date. The street’s bohemian vibes, diverse crowd and walkable nature make it a great spot for any new couples seeking a memorable night out. It’s also the perfect place for a bar crawl (or late-night snack crawl for those who choose not to drink). 

15. Have a Game Night

Game nights are excellent first date ideas because they’re low-stakes and there’s an activity to focus on, taking the pressure off a little. Up-Down Milwaukee is one of the best places for a game night date idea in Milwaukee. 

It’s a bar and arcade with plenty of games, beverages and pizza, so you’ll never be bored with your date. Whether you’re quietly playing on your own pinball cabinets or you’re bonding over a two-player arcade game, you’re guaranteed to be enjoying yourselves. 

16. Cheer at a Milwaukee Admirals Hockey Game

For another sporty first date idea in Milwaukee, attend a Milwaukee Admirals hockey game at the UW-Milwaukee Panther Arena. The fast-paced action, energetic crowd and the occasional fight on the ice make hockey a blast to watch. Hockey games provide an opportunity for an adrenaline-packed evening, and cheering for the home team adds to the fun, even if you don’t care who wins.

Winter Date Ideas in Milwaukee

17. Watch a Milwaukee Ballet Performance

Embrace the arts for this date idea in Milwaukee and attend a performance by the Milwaukee Ballet. Winter is an excellent time to enjoy ballet performances, often featuring classic holiday-themed shows (like the ever-popular “The Nutcracker”) and other beautifully choreographed winter productions. The elegance and grace of ballet make for a sophisticated and culturally rich date idea that’s sure to impress.

18. Attend a Winter Festival

Milwaukee hosts various winter festivals during the colder months, and attending a festival is a fun and festive winter date idea in Milwaukee. These festivals often feature outdoor activities, live music, food vendors and festive decorations. One of the most popular events is the Milwaukee Holiday Lights Festival, which transforms Downtown into a winter wonderland. 

19. Ice Skate at Red Arrow Park

Ice skating is a classic winter date idea in Milwaukee. Take your date out on the ice, preferably on an outdoor rink if you can brave the cold. As soon as the weather is cold enough, Slice of Ice in Red Arrow Park is the place to go to tie on your skates and hit the ice. Keep an eye on their social media for opening dates and get ready for the first good freeze of the year. 

20. Brave a Winter Hike at Whitnall Park

Yes, hiking may normally be a spring through fall activity, but a winter hike can be a fantastic date idea in Milwaukee for anyone who loves nature. Whitnall Park provides a lovely winter landscape, and hiking during the colder months can be a refreshing experience. Bundle up in warm layers, explore the snowy trails and bring some hot cocoa or tea to share. 

21. View Festive Holiday Lights

Milwaukee truly comes alive with festive holiday lights during winter. Explore neighborhoods with elaborate light displays, visit local parks with holiday decorations and experience the magic of the season. Some areas, like Candy Cane Lane, are renowned for their festive lights. Take a trip over there for a sweet winter date idea in Milwaukee during the holiday season. 

Indoor Date Ideas in Milwaukee

22. Have a Classy At-Home Beverage Night

You don’t have to hit a bar or winery to have a nice adult beverage with your date. Set up a cheese board and look into virtual wine tastings to bring the class and elegance of wine tasting into your own home. If you and your date are more into liquor, no problem. Learn to make your favorite classic cocktails with fun online mixology classes.

23. Explore the Milwaukee Art Museum

Visiting the Milwaukee Art Museum is a fantastic Milwaukee date idea for a rainy, chilly or snowy day (or any day that you’d rather spend indoors). It’s full of unique exhibits, and these exhibits and shows rotate over time, meaning there’s always something new and interesting to see.

24. Play Indoor Mini Golf at Nine Below

Who doesn’t love mini-golf? At Nine Below, customers build their own mini-golf experience. It’s a totally unique way to play a classic game. They also have a variety of beers and cocktails to choose from, making this an excellent evening date idea in Milwaukee.  

25. Try Indoor Rock Climbing at Adventure Rock

Rock-climbing indoors? Totally! At Adventure Rock, you can safely try out this fun athletic activity with your date. The day pass also includes yoga if you want to stretch together before or after your climbing session. If you and your date are fitness lovers, this may be the perfect activity for you. 

26. Work Through an Escape Room

There’s nothing quite like the pressure and problem-solving challenges of an escape room to bring you together. There are many excellent escape rooms in Milwaukee to choose from, such as Breakout Games and City 13. Choose one based on your personal interests and desired difficulty level. Working together is a great way to solidify your bond with your date. 

27. Unleash Your Inner Lumberjack

You and your date can try something different and unleash your inner lumberjack by engaging in axe throwing at AXE MKE. This fun date idea in Milwaukee is a unique and unconventional option that blows your average coffee date out of the water. 

Outdoor Date Ideas in Milwaukee

28. Experience a Brewery Boat Tour

Did you know that many of the city’s breweries are accessible via boat? Milwaukee's brewery boat tours offer a unique and scenic perspective of the city's rich brewing culture, and joining a boat tour also makes a fun date idea in Milwaukee. Hop on a boat with a tour like Mondo Brothers and cruise along the Milwaukee River, learning about brewing history while enjoying picturesque views of the skyline.

29. Zip Line Through the Forest at Lake Geneva

For an exhilarating outdoor date, head a bit outside of Milwaukee to Lake Geneva for a canopy tour with Lake Geneva Ziplines & Adventures. You and your date can soar through the treetops to experience the thrill of high-speed zip lines. You can also hop along suspended bridges and treetop ropes courses. This date idea is great for real thrill-seekers who want a day out of town and aren’t afraid of heights.

30. Spot Animals at the Milwaukee County Zoo

Animal lovers will find that going to the zoo makes a great date idea in Milwaukee. The Milwaukee County Zoo provides exciting and immersive animal experiences. You and your date can explore the various exhibits, from the African savanna to the aquatic habitats, and enjoy the company of diverse wildlife. Your admission fee will also contribute to the zoo’s conservation efforts. 

31. Paddleboard on the Milwaukee River

Paddleboarding on the Milwaukee River is a fun and adventurous Milwaukee date idea. Bring your own board or rent from a company like Milwaukee Kayak Company. Enjoy the scenic views of the city from the water, paddle at your own pace and take in the feeling of being surrounded by nature in an urban setting. 

32. Stroll Around the Boerner Botanical Gardens

If you have a date planned in the spring or summer, you’re in luck as this date idea in Milwaukee is perfect for the warmer months. Boerner Botanical Gardens is a haven of natural beauty with themed gardens, colorful flowers and tranquil pathways tucked within Hales Corners just outside of Milwaukee proper. Stroll hand in hand through the gardens with your date and learn a thing or two about local (and not-so-local) plant life.

Free and Cheap Date Ideas in Milwaukee

33. Plan a Day Trip to Cedarburg

A fun and affordable date idea near Milwaukee is taking a day trip to the town of Cedarburg. Of course, there are things you can pay for once you’re there, but simply wandering around this historic little town that feels trapped in time is an experience in itself. 

34. Take a Self-Guided Mural Tour

Do you and your date love art? Explore the Walker's Point neighborhood and discover its vibrant street art with this date idea in Milwaukee. Create your own self-guided mural tour and enjoy the outdoor art scene together. This idea is also completely free. 

35. Bike Along the Oak Leaf Trail

For this date idea in Milwaukee, bring or rent bikes and explore the scenic Oak Leaf Trail, which winds through parks and along the Milwaukee Lakefront. Biking together is a fantastic way to enjoy the outdoors together and get some fresh air. 

36. Benefit From Free Museum Days

Some museums in Milwaukee offer free admission on specific days or during certain hours. A free trip to the museum makes an excellent affordable date idea in Milwaukee. Check the schedules for places like the Milwaukee Public Museum to see when you can visit for no cost.

37. Wander Along the Milwaukee Riverwalk

For a quiet and relaxing free date idea in Milwaukee, take a stroll along the Milwaukee Riverwalk. This scenic pathway features public artworks, shops and restaurants that sit along the scenic river. Even if you don’t spend a single dollar, you’ll have plenty to look at and it’s a wonderful place to have a chat.

So which of these date ideas in Milwaukee are you adding to your must-do date activities list? You could mix and match multiple ideas to create awesome multi-activity Milwaukee dates or enjoy each one as a standalone experience. Whether you’re throwing axes or taking a candlelit cruise on the lake, you’ll have a blast together. 

For even more ways to explore Milwaukee and beyond, check out other experiences happening on Cozymeal.