Milwaukee's Coolest and Most Romantic Date Ideas

It's so easy in winter to just chill on the couch with your date, wrapped up in cozy throws while you marathon Stranger Things for the third time, but that gets pretty boring after a while. Also it would be a pretty awkward first date. So avoid the temptation to hibernate and get out and about: There's still lots of things to do in Milwaukee. Next time you're racking your brain for a unique and actually enjoyable date idea, take a deep breath and peruse these suggestions -- and feel free to take credit for any and all of them.

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Punch Bowl Social Milwaukee
Punch Bowl Social Milwaukee

Explore the Deer District

Kilbourn Town
The newest neighborhood in the city is called the Deer District (read our full guide to the Deer District here). Nestled next to the Fiserv Forum, it's got plenty of bars, attractions, and restaurants to stay busy for a few hours together. Head to Good City Brewing for a beer flight and some pizza, then browse the holiday Christkindlmarket for blown glass ornaments, and finally play a few games at Punch Bowl Social.

Score tickets to a Bucks game

Kilbourn Town
Of course if you're already in the area of the Fiserv, you may as well go see the king of the Deer District, the 2019 MVP Giannis Antetokounmpo. Thanks to him, attending a Bucks game has gone from a snooze fest to an entertaining couple of hours. Even if you or your date isn't a big basketball fan, it's hard to not get swept up in the energy of the crowd when Giannis makes a monster dunk from the free throw line.

Walker's Point
The facility is small, so it’s an easy -- but very informative -- tour. The highlight comes at the end when you get to sample a ton of their alcohol, from maple rum to absinthe. Then head back upstairs and belly up to the bar for some great cocktails. They have a full kitchen now so you can fill your belly with cheese curds and walleye tacos -- you’ll need it.

Flickr/Jeramey Jannene

Beerline B
You’ll laugh, you’ll drink, you’ll sing the theme song to Laverne & Shirley, and you'll learn about bungholes. Tours fill up fast with walk-ins, especially on weekends, so plan ahead and buy tickets.

Go retro at At Random 

Bay View
Yes, At Random is under new ownership, but it's the people from Bryant's Cocktail Lounge, so don't worry. The only things that have changed are that you can sit at the bar now, there are actual set hours, and the thick layer of dust is gone. It's still a romantic, quirky spot to share an ice cream drink with two straws.


Mitchell Park
If it’s a little too early in your relationship to take a trip to the Bahamas, then just head to The Domes instead. The tropical dome is full of palm trees, humidity, and secluded paths for a quick make-out session.

Various locations
Or if you prefer, walk and eat -- or bus and eat, for the lazy among us. Guided tours take you from one restaurant or bar to the next, where you’ll try a new Bloody, chocolate, pizza slice, or whatever fits the theme of your tour. It’s a great way for new MKEans to explore together.

harley davidson museum

Menomonee River Valley
What better way to get your engine going than revving one at the Harley-Davidson Museum? After learning everything you ever wanted to know about H-D, have dinner and drinks at Motor without even moving the car (or bike).

Be an alley cat

Bay View/Lower East Side
Bowling and Milwaukee go way, way back, so what better way to take a fellow Milwaukeean on a date than by lacing up those uncomfortable rental shoes and throwing some balls down a lane? Landmark Lanes and Bay View Bowl are the two primo alleys, with dive bar digs and drink specials that'll give you and your date something to stick around for hours after your games have ended.

Lost Valley Cider Co.
Lost Valley Cider Co.

Walker’s Point
There are a million beer bars in Milwaukee, but only one real cider bar: Lost Valley Cider Co. This Walker's Point spot will give your date something different, especially if they aren’t terribly into beer, thanks to the 30 rotating taps to choose from, cider cocktails, and wine. And yes, there are a few bottles of beer, too.

Get back to basics with dinner and a movie

Bay View
For as long as movie theaters exist, this date will never go out of style. Skip the big multiplexes in favor of the Avalon theater, with its old-school ambiance and full menu of spiked root beer floats, garlic pepperoni knots, Cuban sandwiches, and (of course) popcorn, all of which you can eat at your seat. That said, here’s a date-night pro tip: skip the in-seat dining and grab your meal at Avalon’s ultra cozy and romantic Mediterranean restaurant, Mistral, before the flick starts.

roller derby
Jim Dier

Kilbourn Town
Ladies, what better way to feel a date out than by seeing how loud they cheer for a full-on contact sport that isn’t football? The Brew City Bruisers' season starts in January, and their bouts are raucous, highly entertaining, and full of punny names (like Maiden Milwaukee and Micro Bruisers).

Get locked in a room together...

and then escape. Escape rooms -- where you and a group must figure out how to free yourselves from a locked room -- are popping up all over the place. They can be very beneficial to a relationship: if after 20 minutes you'd rather be anywhere but that room, chances are you're not a good match.

river walk
Keith Homan/

Stroll the Riverwalk

Downtown/Walker's Point
The Riverwalk is a continuous path along the river through downtown and the Third Ward, and it's a great way to explore the city in a new way while checking out some public art. Since it's dotted with bars and restaurants, you don't even need to have a solid plan: just stroll, chat with your date, and stop where it looks interesting.

Grab a truly excellent brunch together

Walker's Point/Honey Creek Parkway
Who says a date can only happen at night? Brunch is a big deal in Milwaukee, so we've got some pretty great restaurants that are only open during the day, like Blue's Egg and Engine Company 3. And just like an evening date, drinking is totally acceptable, so there's really nothing stopping you from thinking outside the dinner box.

1983 Arcade Bar
1983 Arcade Bar

Go for the high score at a retro arcade

Various locations
Lucky for us, arcades are now usually attached or located in bars. They're no longer the places where pimply teens congregate, but socially acceptable hangout spots for anyone with a nerdy bone in their body. The latest to open, Up Down, is a multistory sensory overload of tongue-in-cheek neon signs, pop culture murals, and over 60 games. When you want to have a conversation without the midi music in the background, head out to the upstairs patio.

Lower East Side
Imagine a place where you create your own mini golf holes from piles of weird obstacles, then play them, all while drinking in an underground bar -- that place is Nine Below, and it's a must for anyone who loved putt putt as a kid. This is a great one for group dates, so wrangle some friendly couples and go big with it.

Burnham Park
Kochanski's Concertina Beer Hall is a bar with two stages, Polish drinks, lots of history, and plenty of polka, rockabilly, honky-tonk, and rock shows. If your date can't appreciate that kind of music in a divey, unpretentious bar, then there's probably no hope for your relationship.

Milwaukee Public Market
Milwaukee Public Market

Third Ward
We all know about the Public Market, but it’s not well-known that there are cooking classes offered upstairs. The schedule is up in advance so you can see what strikes your fancy, whether it’s beer cheese soup or profiteroles. Bonus: Those cooking skills may come in handy later on in the relationship.

Drink German-style in a beer hall

Downtown and Glendale
While all of our outdoor beer gardens might be closed for winter, there's still a few places you can get your beer in giant glass liter mugs. Old German Beer Hall downtown serves Hofbrau brews and Usinger's sausages in a raucous atmosphere, complete with hammerschlagen. In Glendale, a north shore suburb, Bavarian Bierhaus brews their own beer in a cavernous beer hall that makes for a fun, communal fish fry.

Milwaukee Art Museum
Milwaukee Art Museum

Check out a museum you haven't been to since high school

Various locations
Milwaukee has a lot of great museums, and you'll have no shortage of talking points on date. You can find the rattlesnake button together at the Milwaukee Public Museum, or take some amazing first date couples selfies in the beautiful Milwaukee Art Museum atrium. For a more traditional evening date, head to a MAM After Dark event, each with a different theme, dancing, cocktails, and entertainment.

Mequon Public Market
Mequon Public Market

Nosh around a food hall

Various locations
Food halls are a thing now, and Milwaukee has a few that have popped up recently. They're great for first dates or blind dates, because who knows what kind of food the other likes? Crossroads Collective has everything from barbecue to handmade pasta, plus a secret entrance speakeasy (I'm not telling you; figure it out together!). Sherman Phoenix has art spaces and shops in addition to food vendors, while the suburban Mequon Public Market has great Greek food and salmon burritos.

Gaze at twinkling holiday lights

Various locations
Elves deck downtown in holiday lights, especially at Pere Marquette Park for the official Holiday Lights Festival. Hop on the Jingle Bus there for a lazy, warm way to see a bunch, and then walk a couple blocks east and freeze while you skate in Red Arrow Park. And if you're feeling nostalgic, drive around Candy Cane Lane, just like when you parents took you when you were six.

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Lacey Muszynski is a Milwaukee writer who needs to schedule a date to Meritage. Follow her on Twitter @worthhersalt.