Happy young couple walking in New York streets.

10 Romantic Summer Dates in Milwaukee

Who needs plain old dinner and a movie when you can go rock climbing or sailing?

Snuggle up at one of Milwaukee’s many free outdoor concerts

Pretty much every weeknight this summer features a free outdoor concert, whether it be in a park or on a hill. Bring your significant other or that person you’ve been meaning to ask out and settle down on a blanket with a picnic. And probably a couple beers (this is Milwaukee).

Double-kayak down the Milwaukee River

Nothing screams romance more than a double kayak. Rent at the Urban Ecology Center or with the Milwaukee Kayak Company, and then, if hungry from all the paddling, take a pit stop at Water Street Brewery or Milwaukee Ale House and have a meal at their riverside patios.

Watch a movie under the stars

Even summer blockbusters where everything blows up are romantic beneath the stars. Settle in at one of Milwaukee’s several free summer outdoor movie series, like the longstanding series at Veterans Park and Monday Night at the Movies in Waukesha. Summer lovin’, indeed.

Enjoy a night out(side)

Milwaukee has no shortage of rooftop and patio dining hotspots, so sip beer and munch on frites on the roof of Cafe Benelux or snag a peaceful riverside table at Stubby’s. Make the date continue by taking a stroll along the Riverwalk where there are many places to snag a kiss (or two).

Take a hike

Impress your date with your ability not to trip over roots by taking them on a hike at the trails near the Riverside Urban Ecology Center or at Schlitz Audubon Nature Center. Continue your rugged outdoor experience by enjoying a couple beers at Camp Bar, a camping themed bar with locations in the Third Ward, Shorewood and Wauwatosa.

Paint in tandem at Splash Studios

Splash Studios, a Third Ward painting bar, is the perfect place to show off your artistic skills to your date. Sign up online for a partner painting (see calendar for available dates). If those dates don’t work, sign up to paint two single paintings. An artist will walk you both through the painting, and your date will leave with something special to remember you by.

Climb at Adventure Rock

All the couples out there with an adventurous spirit: Adventure Rock is calling your names. At this indoor climbing gym, experience the breathtaking adrenaline of reaching the top of the wall with your partner. After, fulfill the appetite you built by having a meal at a nearby North Avenue restaurant, such as Beans and Barley.

Go for a sail on Lake Michigan

Take your partner on a trip back to the 19th century by sailing on the S/V Denis Sullivan, a recreation of an old-time schooner. Register online for a public sail, which meet outside Discovery World, and be sure to bring jackets, as it’s cold on the lake. Relish a fancy seafood dinner after at Harbor House, which is located right next to Discovery World.

Sip craft beers at a new Milwaukee brewery

IPA and craft beer lovers: this one’s for you. Go on a tour or get to know your date over a brew at the bar. And try a new brewery while you’re at it — with Milwaukee’s brewery boom, you and your date have plenty to choose from. City Lights and Pabst are excellent choices.

Be entertained at Ex Fabula

Ex Fabula, a storytelling event organization, is the ideal date for literary buffs. Participate in a StorySlam or just watch, and impress your date with how talented and/or cultured you are.



Since interning for the magazine in spring of 2017, Anna has contributed to both the print publication and website. She has covered topics from women in the workplace to communal gardens and also writes guides to life in Milwaukee. Outside of writing for the magazine, Anna is going back to school at UW-Milwaukee to work towards a career in genetic counseling.