200+ Milwaukee Date Ideas

Milwaukee Date ideas

Recently, my husband and I have found ourselves in a date night rut.

Have you ever been there?

We get a sitter, get in the car and waste 20 minutes figuring out what we want to do. Out of habit, we end up at a familiar place but it got me wondering what else Milwaukee has for dates.

The contributor team put our heads together to bring you the Ultimate Milwaukee Date Ideas Guide for all seasons, interests and budgets. You can use this as is or for inspiration but I promise there is something for every couple. You could even add some mystery and put some ideas in a jar and draw! The sky is the limit, my friend. Happy Dating!! 

Date Ideas by Category

  • Feeling lucky? Try playing the slots at Potawatomi. If you double your money you can afford a few beers.
  • Go for a treasure hunt at American Science & Surplus. See who can find the weirdest thing in less than ten minutes.
  • Pull out the motorcycle or jump in the mini van on a beautiful day and take a ride to Kiltie. This drive-in restaurant is know for its custard but you can also plan to grab lunch or dinner, too!
  • Spend the afternoon channeling your inner American Ninja by taking on TNT Adventure Obstacle Course. Make sure to ease the pain of losing by stopping for homemade ice cream at Kelly Country Creamery afterwards!
  • Leave the kids at home and head over to Rock Snow Park for adult tubing.
  • Head nine feet underground for — wait for it — a round of mini golf at Nine Below. Did we mention that they also serve cocktails, beer and wine?
  • Rent a Bublr Bike for $6/hour and take a stroll around the city together.
  • Head down to the south side of Milwaukee and find the old coal mine, Milwaukee Solvay Coke & Gas Co. You can urban explore and there’s awesome urban artwork everywhere.
  • For the best view of Milwaukee walk down to the McKinley Marina. An amazing view of the city at all times, and you can fish right off the edge of the walkway.
  • Into zombies? iCombat Laser Tag in Waukesha will often do zombie-themed laser tag events. This place is more of a combat-style laser tag facility so if you like that adrenaline rush on your date nights, this is the place for you.
  • Speaking of adrenaline, racing go-carts is sure to get your heart pumping! Veloce Indoor Speedway has grown-up carts that can reach speeds of up to 50 miles per hour!
  • Tour the Milwaukee County Zoo and feed the giraffe. 
  • Go on a horseback ride at Kettle Moraine Ranch
  • Take the dog with you on a long walk at Veteran’s Park. 
  • Volunteer at the Wisconsin Humane Society
  • Head to the Wisconsin State Fair and meander through the animal barns, enjoy a milking demonstration, pet baby goats, and cheer on the pig races. While you are there, hop on the SkyGlider for a romantic ride over the fairgrounds. 
  • Many couples report how much they enjoy a day date. Stroll the MAM during the day and if you are looking to save on admission, visit on one of their free admission days. 
  • Experience the Milwaukee Art Museum at night. Each month is a different themed event.
  • Channel your inner artist and head to Splash Studio. It’s always a good night for #beerandpaint.
  • Art Bar is a bar that’s a coffee shop and an art gallery. Grab a drink or some coffee, and enjoy their pizza while playing pool and viewing their latest installment.
  • Head up to Hubertus (right near Holy Hill.) to a place called Paul Bobrowitz Spectacular Sculpture Garden. Wonder through acres of hand sculpted artwork which is for sale all throughout his land.
  • Get in touch with your creative side and paint together at Uptown Art. Check out their calendar for couples paintings!
  • Take the Brenner Brewing Company tour! This art-focused brewery in Walker’s Point has a variety of amazing beers to sample, all of which are labeled with designs created by local artists. 
  • Boswell Books is a great local bookstore where you can catch readings and other literary events. Perfect for couples who snuggle up on the weekends with their nose in a book.
  • Spend a couple of hours settled in a corner at Barnes & Nobles. A book for her and a book for him. Grab a cup of coffee and discuss what you found interesting. 
  • Grab your favorite book of poetry and a blanket and sit under a tree at South Shore Park, reading aloud to each other. 
  • Prepare a book-themed dinner together. 
  • Invite other bookworms over and host a literary-themed game night. 
  • Watch a film-adaption of a book you both enjoyed.
  • Choose a book for you both to read and then find a cozy spot at your favorite area coffee shop to hold your own private book club. Better yet, read a book that will pour into your relationship like The Five Love Languages.
  • Use our Little Free Libraries guide to go on a book treasure hunt! Explore a new neighborhood and see who can find the quirkiest book. 
  • Take a tour of Great Lakes Distillery, and sample a flight of 6 spirits. Right around the corner is MobCraft Beer, the only crowd-sourced brewery in the Milwaukee area that is a must try! 
  • Enjoy a beer in the park at one of Milwaukee’s awesome beer gardens.
  • Milwaukee has some great local breweries and each one has its own personality. We suggest one of these:  Lakefront Brewery, Third Space Brewery, or Enlightened Brewing Company
  • Looking for something new and fun to try?! Head to Polka night at Kochanski’s Concertina Beer Hall. Enjoy Polish and German beer while taking in the vintage vibe at this historic beer hall. They are known for having the most Polish beers than anywhere in Wisconsin and for their lively Polka nights!
  • Schedule a Sunday morning brunch date and enjoy half-sizes Bloody Mary’s and a 1-mile walking brunch tour. Drink substitutions available.
  • PedalTavern is a fun option for a big group date! Be prepared…it’s a workout and you might want to UBER home after pedaling the tavern on wheels.
  • Enjoy free wine and beer tastings every Saturday afternoon at Three Cellars.
  • Sample some squeaky cheese curds on the tour at Clock Shadow Creamery.  
  • Take a tour of the Palermo’s Pizza Factory. You get a tour, t-shirt and (non-frozen) pizza for $10.
  • Grab a cup of joe at the Lakefront Colectivo, then stroll down Lincoln Memorial Drive and enjoy breathtaking views of downtown.
  • Admission is free for all visitors on the first Thursday of the month at the Milwaukee Public Museum, open that day until 8 p.m.
  • $2 tacos at Bel Air Cantina on Tuesdays and Thursdays and don’t forget to order the $5 margarita! 
  • Take in a free weekly concert at 414 Music Live at the 88.9 Radio Milwaukee headquarters. Every Thursday starting at 5:30pm.
  • Pack a picnic or grab a bottle of wine and explore Milwaukee’s music scene Tuesday evenings from 6-8pm at Chill on the Hill. Runs June-August.
  • Head to Conejitos, voted #1 Cheap Eats in Milwaukee. Fill your hunger without breaking the bank! There’s literally nothing over $5.
  • Explore a farmer’s market.
  • Grab $2 tacos on Tuesdays and Thursdays at Vagabond. The atmosphere is a throw back to all things Americana, from 1970’s Airstreams and boomboxes to a wall of retro speakers merging street food and street life.
  • Make a thermos of hot cocoa, hop in the car with your hunny and look at holiday lights around Milwaukee!
  • Marcus Theaters have $5 Tuesdays so you can see the latest blockbuster without breaking the bank. 
  • Dreaming of warm weather and umbrella drinks? Escape to Milwaukee’s famous tiki bar, Foundation Bar, and sip on their famous Mai Tai and experience Polynesian culture. 
  • Make plans to enjoy one of Milwaukee’s oldest original cocktail lounges. Bryant’s Lounge has been around since 1938 and patrons will enjoy plush velvet walls, dim lighting, and vintage tunes. Cozy up in a booth and sip on a signature cocktail. Tip: Ask the bartender to surprise you!
  • Ever wonder what that neighborhood dive bar is like? Pick one, grab a beer, and see what it’s really like! If you’re really feeling adventurous, try the scorpion shot at Bad Genie (yes, it involves a LIVE scorpion) or see if you can get the coveted Wolski’s bumper sticker.
  • Swingin’ Door Exchange is a great option for experiencing a dive bar. Enjoy some PBR!
  • Straight Shots is another friendly neighborhood bar with a few pool tables, tvs and inexpensive drinks. It’s a great place for a couple to let loose and have a little fun!
  • Go on a date At Random. Call ahead to make sure they are open but they are well-known for their retro cocktails and unique dark n’ cozy vibe.
  • Grab a drink and a game of pinball on retro thrown back night (Fridays) at Mad Planet, a dance club featuring hometown bands & national acts plus a retro night with DJs.
  • Love the great outdoor? But don’t actually want to be outside? Grab a drink at Camp Bar. Located in Shorewood, Wauwatosa and Milwaukee.
  • If you enjoy hitting the clubs, but haven’t found yourself at La Cage, you’ve gotta add it to your date night bucket list! Considered to be on of the best nightclubs in Milwaukee several times over, this LGBTQ (but EVERYONE welcome) entertainment club is known for its amazing beats, dance floor and reasonably priced drinks. 
  • Catch some good ol’ fashioned improv and laugh until your sides hurt at ComedySportz. Laughter is truly the best medicine.  Admission is only $10. Bonus- they serve booze!
  • See a Pat McCurdy Show. Pat’s shows are legendary to Milwaukeeans. Get ready to sing your heart out at a show, while enjoying a local beer!
  • Attend an open mic night at Milwaukee’s Comedy Cafe
  • Binge watch your favorite TV comedy. We recommend The Office, Parks and Rec, Blackish, or New Girl. Take it up a notch by booking a hotel room so the kids are guaranteed to stay away! 
  • Solve a hilarious murder case while you feast on a fantastic four-course plated dinner at The Dinner Dective.  Just beware.  The killer is hiding somewhere in the room, and you may find yourself as a Prime Suspect.
  • Find an upcoming show from Milwaukee Comedy, who will often have events at area breweries. The best of both worlds! 
  • Jim Gaffigan brings his comedy tour to Milwaukee pretty much every December and there is always a show that benefits the Riverwest food pantry. Put this one on your calendar and get your tickets because this is date night GOLD. 
  • Project Hunting at The Container Store, Home Depot, or Menards can be a DIY couple’s dream date. Dreaming of a renovation? Take a romantic stroll through the aisles of your favorite home DIY store.
  • Join in on the chalk painting trend and take a furniture painting class together.
  • Plan a date night at Pin-It LIVE’s studio. Pick a project from exclusive Date Night pin board and create something together. 

Mark your calendars and plan to attend one of Milwaukee’s fantastic annual festivals:

Other great Milwaukee area festivals to check out with your sweetheart:

  • Take a MKE food and city tour, either walking or by bus, and explore different areas of the city, all while feeding the foodie in you. Old World 3rd St Tour is located in one of the old German neighborhoods where you can experience the old world traditions, foods, and drinks. The Village of Wauwatosa Tour is pedestrian-friendly village tour with Italian, French, and Belgium cuisines. Plan to go on a Saturday morning so that you can shop the infamous Tosa Farmers’ Market.
  • Take a cooking class at the Milwaukee Public Market.
  • Visit the Italian neighborhood and indulge yourself on an Italian sandwich and gelato from Glorioso’s.
  • Grab a giant cheeseburger at Kopp’s. They’re about as big as your face! Don’t forget custard for the ride home. 
  • Experience a unique Milwaukee tradition and grab hot ham and rolls at Rupena’s in West Allis.
  • Plan ahead (we’re talking February/March) and get two seats to the famous summer Farm Suppers at Parkside 23 in Brookfield. $100 a head gets you a 5 course meal complete with beer and wine pairings served al fresco right smack dab in the middle of their on-site farm. These sell out every year for a reason! Can’t quite swing the Farm Supper? Stop in on a Wednesday night for 1/2 price bottles of wine and the Creamed Corn. (Trust us. It’s legendary.)
  • Mix and match 5 tacos at BelAir Cantina. Everything from chicken to lobster to vegetarian. Make sure to try the Korean Beef!
  • Love pizza? Take the Palermo’s Pizza tour and enjoy a slice at Pizzeria 3301
  • Have a sausage party at Vanguard. Did you know they have brunch? You can’t go wrong with tubed meats.
  • You don’t even have to be a baseball fan to appreciate the impressive view from this TGI Friday’s at Miller Park
  • Grab lunch or dinner at any of the local vendors in the Milwaukee Public Market and then spend a couple hours window shopping in the Historic Third Ward.
  • Enjoy brunch or dinner at this locally-sourced hidden gem. Cafe Corozon has an amazing atmosphere, delicious drinks, and unique entrees. 
  • Need a cozy place for dinner? Check out Soup Bros! Soups change daily but the Roasted Red Pepper Bisque and the Stew and Sandwich seem to be pretty popular.
  • The Red Light Ramon serves tonkotsu ramen and boozy slushies with a funky vibe. It’s only open Wednesday thru Sunday 6pm-130am.
  • Kyoto, in the Third Ward, has great sushi and Asian food. We also love Screaming Tuna
  • Grab dinner on a rooftop at any one of Milwaukee’s rooftop dining spots.
  • Grab an amazing brunch at Blue’s Egg.
  • The Mad Rooster Cafe has amazing food … and an especially amazing brunch.
  • Grab a bag of THE BEST kettle corn in just about any flavor you can think of at Pop’s Popcorn in Muskego.
  • Do you know the password? Head to the Safe House for an odd but funny venue for dinner.
  • Get cozy at the Smoke Shack where the meats are dry rubbed, slow smoked and sauced by you.
  • Book a babysitter (or grandparent!) for a Sunday morning and try out a new brunch place. Nothing makes a weekend better than brunch and a bloody with your love. 
  • Get an Instant Pot. We’re serious. Then cook this amazing Beef Stew that has 16 oz of red wine in it, serve with a crusty french baguette and thank us in the morning. 
  • Track down your favorite Food Truck to get dinner on the run. We particularly love Gouda Girls and Meat on the Street
  • Grab your hunny and take a historical MKE Walking Tour. Insider tip: there are indoor skywalk tours in the winter!
  • Visit Milwaukee’s tea room and walk around the beautiful, historical Pfister Hotel in downtown. With 124 years of history, this hotel will make you feel like you have be transported to Historic Milwaukee.
  • Go on a walking tour in the Historic Third Ward. Added bonus? Explore and sample 5 restaurants along the way.
  • Visit the  St Joan of Arc chapel on Marquette’s campus! It’s the oldest church in the United States. It’s oldest structure in Milwaukee and was shipped from France.
  • Wait until the kids are in bed and cook an easy and delicious meal for two! Try cheese fondue with plenty of fun dippers, like bread cubes, sliced pears, baby carrots or mini tomatoes. For dessert, try this yummy chocolate pudding with a grown-up twist. 
  • Make cooking a meal together the date experience, from start to finish. Set your menu, head to the grocery store, and come back to do the whole prep, serving and clean up as a team. Good relationship building skills too! 
  • Experiment with making your own interesting cocktails in the comfort of your own home bar.  
  • Instead of ordering pizza, how about make your own and enjoy a movie? Put the kids to bed (early), and craft your own speciality pizza. After dinner, have a movie ready to go and some popcorn and spend the night curled up watching your favorite movie.
  • Hit up your local craft store and buy some inexpensive canvases and paint and a bottle of your favorite wine and spend the evening painting.
  • Exercise together — here’s a couples yoga routine that you have to try!
  • Take a blanket out in the back yard and enjoy just being together, gazing at the stars and sharing thoughts and catching up on each other.
  • Don’t have time to travel? Set up a tent and sleeping bags in the living room. Add a strand of twinkling lights if you want the effect of stars.
  • Learn how to play cribbage. Make it interesting by making a friendly bet 🙂
  • Make it a double-date and invite over another couple with kids. The kids can destroy the playroom while the four of you drink beer and play Settlers of Catan. Win-win. 
  • Take a boat cruise in style along the Milwaukee River. 
  • Rent a kayak and see the city in a new perspective.
  • Pack a picnic and a blanket and follow the path out to the beach at Doctor’s Park in Fox Point. The walk is worth the view.
  • Does that scene from Serendipty give you a little flutter? Recreate your own serendiptious moment and go ice skating at Red Arrow Park. It’s free to skate but you will need little cash for skate rentals.
  • Cozy up next to your honey in front of the fireplace at County Clare with a pint and their famous meatloaf while listening to Irish music. 
  • Buy an hour pass at Bounce and play their vintage arcade games, laser tag or air-hockey.
  • Stop in at Milwaukee’s own kit store, Gift of Wings, located at the lakefront. Then fly your newly purchased kite at Lake Park.
  • Sprecher Brewery is known for their locally-made sodas. Leave the kids at home and sample sodas. Don’t forget to stop at the gift shop and pick up your favorite for the kids.
  • Bundle up and grab your sleds and enjoy the sledding hill at Whitnell Park….in the dark! Warm up with the coffee or hot chocolate at the concession stand.
  • Go ice skating at Red Arrow Park.
  • Explore MKE’s past at the quirky Chudnow Museum.
  • Go hog wild at the Harley-Davidson Museum. After you’re done learning all there is to know about Harleys have dinner and drinks at Motor.
  • Meet your husband at your favorite coffee shop after work and enjoy an hour working through a crossword together.
  • Learn how to make your favorite fancy coffees at home by taking a Coffee Class at Stone Creek. Choose from ‘Espresso 101’, ‘Homebrewing’ and the ‘Factory Tour.’
  • Take the tour at Clock Shadow Creamery to see how true Wisconsin cheese curds are made. Bonus – getting to sample that squeaky goodness at the end. 
  • Make it easy to enjoy dinner and a movie at the Fox Bay Cinema Grill, where you can order from your seat and dine while watching your flick.
  • Is date night on Tuesday this week? Head to a Marcus Theater and catch a flick for only $5.
  • Classic movies? Check. Romantic art museum? Check. Every Wednesday, Milwaukee film historian Dale Kuntz hosts viewings of titles from his collection of rare classic 16 mm movies at the Charles Allis Art Museum. It’s a perfect winter night in, and with admission at just $7 per person, it won’t break the bank.
  • Looking for movies with purpose? Head over to the UWM cinema for gripping films and documentaries that are sure to inspire deep conversations.
  • Of course, the big event of the year for Milwaukee movie buffs is the Milwaukee Film Festival
  • See some live music at the Pabst, Riverside or Turner Hall. Turner Hall also has a lot of $10 shows where you can catch a great up and coming band.
  • Cozy up on a blanket and listen to music at Jazz in the Park, located in Cathedral Square. 
  • Caroline’s features live jazz, blues and more from musicians in the greater Milwaukee area and beyond.
  • Check out an indie band at the Cactus Club
  • Summerfest is one of the best ways to see your favorite artist in concert! This ultimate date idea includes shows, food, drinks, and so much more!
  • Hear some of the best local and national musicians at Jazz Estate, a high end jazz bar with live music every weekend.
  • Milwaukee has a ton of hidden gems where you can grab an outdoor concert. Added bonus: they are generally free!
  • Dining with the Diva’s at Hamburger Mary’s is one of the most popular drag shows in Milwaukee that you will want to make reservations for! Two shows, every Friday and Saturday night. 
  • Pack a picnic and venture along the Hank Aaron and Oak Leaf trails in Lakeshore State Park. You’ll find both natural beauty and the perfect spot to enjoy city views.
  • Climb the North Point Lighthouse
  • There’s something romantic in the transcendent beauty of the lakeshore nature preserve at Schlitz Audubon. Take advantage of their impressive lineup of programming or keep to yourselves on a private hike.
  • Grab an annual membership for $45 and use it any of the three locations of the Urban Ecology Center. Outdoor lovers will enjoy free kayaking and canoeing, snowshoeing, cross county skiing, and rock climbing. 
  • Craving some warmer, tropical weather?! Take a stroll with your honey and take in the sights (and heat) in tropics at the Mitchell Park Conservatory (aka The Domes). Consider a day date on a Monday because Milwaukee County residents get in free!
  • Hunt for beach glass at Klode Park Beach. Or if you’re brave enough doing a little cliff diving.
  • Lace up your hiking boots and pick out the perfect trail for you and your sweetie to tackle together. Lapham Peak is a really popular one and Lion’s Gorge is a team fave!
  • The best spot around to take in the natural splendor of the fall colors is Holy Hill. The scenic tower is open May through October. Make the 30ish mile drive and be awestruck by the beauty of this landmark. 
  • Whether you stay on the property at the American Club Hotel or at a cozy B&B, the historic Village of Kohler offers plenty to explore, with golf, shopping, outdoor activities, and many restaurants to delight your palate.
  • Have you dreamed of staying at The Dragonfly Inn or do you enjoy the romantic charm of a quaint B&B? We suggest checking into the Pedalr’s Inn, located a few miles west of Milwaukee. Read Sarah’s review of the inn for an insider’s perspective. 
  • Eat dinner in downtown Milwaukee and check into one of the beautiful hotels for the night. Visit doughnuts and coffee from Holey Moley for breakfast the next morning. 
  • Watch a star show at the UWM Planetarium.
  • Grab a show at the dome theater at the Milwaukee Public Museum. You can visit the mysteries of the sea, go back in time with dinosaurs, or visit the jungles of Africa!  They have both 2D and 3D shows. 
  • Brewers playing a home game? Score $1 Uecker seats at the box office. Only available on the day of the game.
  • Play Ping Pong at Evolution Gastro Pong, a modern ping pong lounge with rooftop seating and American eats.
  • Build your own mini golf hole and then enjoy a round on miniature golf at Nine Below
  • Bring out your competitive side and play skee-ball at Lee’s Luxury Lounge or G-Daddy’s.
  • Check out a Bucks game.
  • Sign up as a couple for a dance class at Danceworks. They offer everything from Barre to Hip Hop.
  • Check out a Milwaukee Wave game. 
  • Like hockey? A Milwaukee Admirals game would make a great date night activity. 
  • During the summer months, head to The Umbrella Bar at The Rock Complex in Franklin to enjoy the best sunsets in the city plus watch baseball games down below. They also hold Food Truck rallies featuring Milwaukee favorites. In the winter, go tubing or snowboarding on their slopes!
  • Savor the interesting ice cream flavors at Purple Door.
  • Grab dessert at Leon’s. No one can resist their custard!
  • From Red Elephant Chocolate to Treat Bake Shop and the many vendors of the Milwaukee Public Market, the Historic Third Ward will put the “sweet” in your sweetheart.
  • Go on a walking tour of Brady Street, where you will find some of the best sweet shops in Milwaukee. Sciortino’s Bakery has long had the last word in Milwaukee’s offering of delicioso baked goods. Stop by for a late-afternoon cannoli on the corner of Humboldt and Brady, then head west and duck into Rochambo Coffee & Tea, Nomad Pub, Balzac or Up and Under.
  • Cedarburg is a great place to fulfill your sweet tooth. A picturesque small-town, Cedarburg is home to bakeries, chocolate shops, wineries, and breweries. Take a couple of hours and walk downtown
  • Why not eat dinner at home and then head to Buckley’s for a decadent dessert and coffee?! Rumor has it that the Carrot Cake is delicious choice.
  • Grab ice cream or custard at any of Milwaukee’s Best Ice Cream and Frozen Custard spots.
  • Visit Dan-O’s Donuts at a local farmer’s market for fresh outta the oil donuts that will melt in your mouth. Made right in front of you and coated with fun flavors. Once you walk around a bit, you’ll burn off enough calories for a second bag. 
  • Stroll down Main Street in Waukesha and grab some heaping scoops from Divino Gelato before heading toward the river for a romantic walk. 
  • Register for a Chocolate Pairing Class at Indulgence Chocolatiers. Learn about the wine, beer, bourbon, etc that goes best with your favorite chocolates. Expert level romance right here. 
  • Experience the Rocky Horror Picture Show, with live performance, at midnight on Saturdays at the Oriental Theatre
  • Come and listen, or if you have a story that fits the night’s theme, through your name in the hat for a chance to take the stage at Ex Fabula. Truly, there is no other experience like this.
  • Enjoy fine middle eastern cuisine and take in a (free) belly dancing show at Casablanca on Brady.
  • There’s always good shows at the Rep Theatre. Check out their website for tickets.
  • Holiday date nights are always extra magical and the tradition of seeing A Christmas Carol is one many Milwaukeeans hold dear.
  • Learn about and taste wine at one of Thief Wine’s tasting events
  • Sample wines and tour this historic limestone building, constructed in the 1860s on the banks of the Cedar Creek.
  • Plan a progressive dinner date, pairing different wines with your appetizers, entrees, and desserts. 
  • Take a wine class with a wine specialist at Vino100 Milwaukee.
  • Located in the Third Ward, Swig serves small plates, martinis and of course, wine!

Do you have a date night favorite?

We would love to hear about it!

Leave your ideas in the comments or send them to us at [email protected].

Although this guide is not sponsored, affiliate links are used.

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One Response to 200+ Milwaukee Date Ideas

  1. Amber August 2, 2017 at 4:40 pm #

    This list is AWESOME. So many great ideas! Thank you!!

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