Top Ten Places for a Date in Milwaukee, Wisconsin

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Romantic dates like visiting Milwaukee's Summerfest. Photos by Christa Romano
Romantic dates like visiting milwaukee’s summerfest where major acts rock the city. Photos by christa romano

Milwaukee Date Ideas for Travelers

By Christa Romano

Standing on the Milwaukee banks of Lake Michigan, watching the ripples being carried over to the horizon by the warm summer breeze, I couldn’t help but think about how wonderful it would be to share this sight with someone special.

There are so many fun things to do as couples, but I was here without my significant other.

While I am in full support of solo travel, of being independent, and seeing the world for yourself, I found that nearly every establishment I hit while in Milwaukee could make for a really interesting and fun romantic date spot.

Milwaukee is a perfectly romantic cityscape, famous for its festivals, its nightlife, and for its vintage Americana — small-town charm in a large city.

The following is a top-ten list of date ideas, catering to the city of Milwaukee, that could literally suit any sort of couple, be they music or food enthusiasts, motorcycle lovers, or even science nerds.

If you can’t make your way out to the southeast corner of Wisconsin, feel free to use this top-ten list simply as a guideline for how to pick and find interesting and unusual places to take that special someone. Milwaukee, however, is featured here for a reason: It’s a city that has raised its residents in a culture of celebration, and if that is not reason enough to call it a hot-spot for dating, what is?

Number 1: Summerfest

Milwaukee is home to Summerfest, the largest music festival on the planet and the city’s biggest event of the year. This takes the cake as the best place to take a date because you can’t do much better than to take your date to his or her favorite indie band.

­­Over the 11 days that Summerfest takes place and the 700+ bands that pass through there, there is bound to be at least one show to excite anyone. You can also play all of those cliché-date carnival games, dance, eat, drink, and be provided with endless entertainment for the entire day and night.

Hundreds of thousands of people show up for SummerFest every year
Hundreds of thousands of people show up for summerfest every year

You can always get in for less than $15 (or for free, depending on what the promotion is that day. Eg, 3 cans of food for a free pass), allowing you to see as many concerts as you can handle, from big pop acts to jazz bands of the sixties.

Number 2: Safe House

Hidden in a secret passageway in the heart of the city, the SafeHouse is truly a one of a kind destination that will probably have you remembered as the coolest date ever (even if your chemistry is lacking).

It’s a true speakeasy, a restaurant, a rowdy bar, an American history museum, and a spy hide-away all in one. With a theme so thoroughly explored that it rivals the décor of an Epcot restaurant, it is impossible not to have something to talk about while at the safe house.

From the minute you whisper the secret password to the security guard, to the time you order “The Silencer” at the bar, you are surrounded by an amazing and authentic display of Cold War nostalgia, hilarious surprises on unsuspecting patrons, and the feeling that you are a part of a well-kept city secret.

A vintage motorcycle on display at the Harley Davidson Museum
A vintage motorcycle on display at the harley davidson museum

Keep in mind that it is literally a mission-impossible to get a Milwaukee local to reveal what the secret entrance password is. “The Control” is generally pretty understanding, but do be prepared to take a “Spy Test” if you don’t know what those magic words are.

Number 3: Harley Davidson Museum

All open road leads to Milwaukee, the birthplace of the Harley Davidson Motor Company, which dates all the way back to 1903. In order to preserve the historical niche of its classic motorcycles, the Harley Davidson Museum was established fairly recently, in 2007, but already attracts an annual 350,000 visitors from all over the world.

This museum is especially interesting because it demonstrates that motorcycles are a “cage-less” way to travel, and offers exhibits about an important part of American history and culture, documenting the past 100+ years that motorcycles carried our goods, our services, and our ancestors (such as Elvis Presley and Evel Knievel) around the country.

The Milwaukee Public Market is a great place to grab lunch, pick up locally produced goods or attend a cooking class.
The milwaukee public market is a great place to grab lunch, pick up locally produced goods or attend a cooking class.

The best day to check out the Harley Davidson Museum is Friday. In addition to everything the museum has to offer inside, the parking lot is transformed into a vintage car show each week. Milwaukee residents gather there starting at 5 p.m. to show off their old fashioned hot rods and  Model Ts to anyone caring to stop by.

Number 4:  Cooking Classes

There’s that old saying: the way to a man’s heart is through his stomach. At the same time, what woman wouldn’t enjoy a man cooking for her? You can feed your bellies, your brains, and your hearts by learning to cook a fabulous meal together.

At Madame Kuony’s Kitchen, located on the lofty second floor of the Milwaukee Public Market, cooking classes are offered July through August. Whether you are an amateur chef or only know how to cook microwavable soup, classes are offered to suit all levels of cooking experience.

Prices range from $20-$90 per class, depending on if you want to make gourmet salads or five-course Tuscan delicacies.

After class you can head downstairs to peruse the dozens of local vendors, selling goodies like homemade fudge to hand-packaged spices, or even participate in a wine tasting.

The German Hofbrauhaus restaurant and beer garden is one of the many places in the city that very ethnic cuisine and drink is offered.
The german hofbrauhaus restaurant and beer garden is one of the many places in the city that very ethnic cuisine and drink is offered.

The Public Market website also has a listing of events that you could try to coordinate into your date, such as a Food Network cooking show, a movie or a live speaker.

Number 5: Ethnic festivals

Dating tip: people like it when others take an interest in their personal background. If you really want to impress someone, find out where their ancestors came from and spend a day exploring one of the many ethnic festivals that Milwaukee offers literally every weekend of the summer.

It seems that in Milwaukee, the world comes to you. There is essentially a specific festival for any heritage, including Festa Italiana, Oktoberfest, The Cedarburg German Festival,  French Bastille Days, The Caribbean Festival, Polish Fest, The African World Festival, Mexican Fiesta, Arab Fest, the Indian Summer Festival, Irish Fest and others.

If it’s not an exploration of personal history you’re after, these festivals are still completely worth traveling to for the authentic cuisines,  free entertainment, and imported goods.

Nicknamed “The City of Festivals,” Milwaukee also offers, not surprisingly, dozens of other festivals throughout the year, ranging from celebrations about the gay community during Pride Fest to locally grown strawberries at Strawberry Fest.

The delicious scallops at Umami Moto, a restaurant that combines French and Asian cuisine
The delicious scallops at umami moto, a restaurant that combines french and asian cuisine.

Most take place on the picturesque lawn of the Henry W. Maier Park, located right on the shore of Lake Michigan, providing patrons with a constant breeze and an always scenic backdrop.

Number 6: Dining Out in Milwaukee

A dinner is always a good option for a date, but the same old types of restaurants can become redundant. All down Wisconsin St and Michigan St. are dozens of unusual restaurants and bars for whenever you feel like expanding your palette.

While Milwaukee does offer a wide selection of ethnic cuisines that come standard in almost any city (e.g. Italian, Japanese, Mexican, etc.), you can get more exotic with the city’s offerings of Cuban, Serbian, Cantonese and Cajun restaurants.

If you’re looking for a more casual ambiance, Milwaukee is famous for its “Fish Fry Fridays.” At the end of each workweek, you can try out the fish fry at dozens of restaurants around the city, always for a special low price. The Lake Front Brewery does it and offers you a cold, locally-produced brew with a hot beer-battered fish and all the trimmings.

An exhibit dedicated to music legend, Les Paul, displays the first ever electric guitar-- a block of wood covered with wires and metal knobs!
An exhibit dedicated to music legend, les paul, displays the first-ever electric guitar– a block of wood covered with wires and metal knobs!

Number 7: Discovery World

There is no one word that can describe this place — it’s an interactive science museum, an aquarium, and a beautiful lakefront destination.

But whatever you decide to call Discovery World, this fascinating establishment is a great place to learn more about what your date finds interesting.

There are two sides to the building, one focusing on nature and the other focusing on all things man-made. On the nature side, you’ll see amazing grand scale exhibits, such as the weather exhibit, at which you can create a synthetic thunderstorm complete with a pounding rainfall.

On the man-made side, there is a fascinating section on music legend, Les Paul, which includes the first-ever electric guitar. While passing through you can learn first hand how electric guitars work and how they evolved.

Locally produced vodka at the Milwaukee Great Lakes Distillery
Locally produced vodka at the milwaukee great lakes distillery.

Even if you’re not interested in what goes on inside the building, there are frequent outdoor evening events.

While the sun sets over Lake Michigan, snuggle up on a blanket on the Discovery World lawn to listen to a free ethnic music concert. These acoustic bands range in genre from Bluegrass to Salsa and perform every Wednesday from July through September.

In August, Discovery World also shows big-screen movies outdoors under the stars every Friday at “Flicks and (you guessed it) Fish Fry.”

Number 8: Milwaukee Distillery Tour

If you’ve ever been to a wine tasting or toured a brewery, you know that these are great places to take a date. You get to learn together about how your favorite drinks are made while, more importantly, working on a buzz that makes everything just a bit more fun.

The owner of the Great Lakes Distillery give details about each liquor produced there on one of the distillery tours.
The owner of the great lakes distillery give details about each liquor produced there on one of the distillery tours.

A distillery tour, like the one you can get at Great Lakes Distillery, takes a unique spin on your typical daytime boozing. The small and intimate distillery is a one-room building that produces the liquor, bottles it, labels it, and then sells it to you via cocktail right there at their bar.

Friday Night Flights

Milwaukeeans have recognized the Great Lakes Distillery as a fun place to go on Friday evenings for a free tour and a liquor tasting.

At just $3.00 for a flight of three liquor products, you’ll get one of the passionate workers demonstrating how to properly sample and take in the flavors and aromas of any kind of liquor they produce there.

Before you go: know in advance that the liquor is meant to be sampled at room temperature for maximum flavor and taste. Also, be prepared to clean your palette with only water. As prepared as you may be, it will always be fun to see one another try not to make the “I just swallowed fire” face.

An outside view of the Lake Front Brewery
An outside view of the lake front brewery, in milwaukee.

Number 9: Brewery Boat Tour

Not brave enough to take a mouthful of luke-warm grappa down? Milwaukee is home to three big-time breweries; including MillerCoors, Lakefront, and Sprecher breweries.

Combining two key features of the city, beer and waterfront activities, brewery tours by boat are available.

On a hot summer day, nothing is better than floating to and from brewery tours with a chilled beer in your hand and the spray of mist from the lake.

Even non-beer-drinkers can enjoy the ride with a chilled Sprecher Root Beer.

If you cant decide which brewery you want to visit (or if you just want to hold your date hostage on a boat for as long as possible),  The Brew City Queen II and the Milwaukee Maiden offer a river cruise that stops at three different microbreweries every Saturday and Sunday afternoon of the summer.

This brew cruise is a four-hour voyage down the Milwaukee River to the Lakefront Brewery, the Milwaukee Ale House and Rock Bottom Brewery.

The Wisconsin Cheese Mart offers a variety of over 175 locally produced cheeses.
The wisconsin cheese mart offers a variety of over 175 locally produced cheeses.

Number 10: Wisconsin Cheese Mart

When you visit Italy, you eat pasta. When you visit Mexico, you order a burrito. And when you visit Wisconsin, you try the cheese.

For a casual way to indulge in your senses, the Wisconsin Cheese Mart will provide you with strong, appealing aromas and tastes, accompanied by the sounds of clinking glasses and a mature crowd looking for a night filled with conversation and relaxation around the cheese bar.

You really can’t get more “Wisconsin” than spending an evening sampling different cheeses with the perfect locally produced beer or wine.

At the cheese ba,r you can create your own cheese flight when you choose from a variety of 175 different artisan kinds of cheese while spending less than $5 (and that includes your drink!).

Located on Old World Third Street in downtown Milwaukee, The Wisconsin Cheese Mart has been around since the 1930s.

This was a time when the local dairy industry was at its height and cheese-producers from all over western Europe were immigrating to Milwaukee for the abundant supply of milk for their trade.

Cheese production and consumption has since become a quintessence of Wisconsin culture. It is at the old and famous Wisconsin Cheese Mart that you will find the best collection of the finest cheeses in the state.

Now get out there and impress someone with your new date ideas. Good luck!

Christa Romano



Christa Romano is a former GoNOMAD Editorial Assistant and a digital nomad who lives all over the world.