They don’t call Milwaukee the “Hollywood of Southeastern Wisconsin” for nothing [citation needed]. We’ve got our fair share of locally born, bred, or based celebrities, and The Squeaky Curd is sitting down with them at local watering holes to talk craft beer, Summerfest shuttles, Bloody Marys, and Milwaukee.

The Walker’s Point neighborhood of Milwaukee has become the go-to spot in town for eclectic food and happening nightlife. But Jerry Stenstrup and his wife, Cheryl, opened up local fixture Steny’s Tavern & Grill decades ago in the once predominantly blue-collar, rough-and-tumble district. We sat down with Jerry and his son Ryan at their namesake bar to talk Milwaukee’s renaissance, and their own.

Steny’s Tavern & Grill in Walker’s Point, Milwaukee, WI. All photos by Joe Powell for The Squeaky Curd.

The Squeaky Curd: As a Milwaukeean, where do I probably know you from?

Jerry Stenstrup: I’m the mayor of Walker’s Point. You should probably call this “Local Bar Owners in Local Bars” for us.

TSC: In your opinion, what would you like me to know you for?

Ryan Stenstrup: If you come to (Steny’s), you’re gonna see me, you’re gonna see (Jerry). The owners are here working, fixing things, talking to folks. This isn’t some hobby business for us. Steny’s is us.

TSC: What’s your connection to Milwaukee?

JS: I grew up on the South Side, and got into the serving business back in high school. Back then nobody cared much if a bunch of kids threw a party in a public park – so I learned to turn a profit from it. I’ve been in the bar business ever since I graduated.

My wife and I lived above this bar after we bought it. Ryan was born up there. Business was so good I had to tear down his swing set and backyard to build a beer garden.

Ryan and Jerry Stenstrup in their namesake Milwaukee landmark bar.

TSC: What makes Milwaukee a desirable place for you to live and work?

JS: Milwaukeeans are very loyal.

RS: It’s small, people know each other. The bar business can be tough, both from the government regulations and the changing tastes of patrons. But the people still make it worth it at the end.

TSC: What got you started and kept you in Walker’s Point?

JS: Back in 1985 (when Steny’s first opened), there was no “bar district” in Milwaukee. Down here, we were all a bunch of tiny little 1-room bars. I was working at the MAC and drove by these “shot-and-a-beer” bars every day on my way home. This was the Old Tapper, but had been the Cortavox since the 40’s. When I got it, it had just 9 stools and a pool table. LJ, our first waitress, is still on as GM here.

We had it real good pretty quickly, with our block kind of turning into the going out district. We had lines out the door each night. But in the 90’s, Water Street started opening up and we evolved into a sort of biker bar, ‘cuz they weren’t going out up there. We’d have 30 bikes lined up outside.

Walker’s Point’s has always been the gay district, but everyone’s always welcome here. In 2000 we added food and expanded our hours. Now people are here all day.

TSC: Steny’s was kind of the first place I can remember in Walker’s Point serving good food, getting people to come down here for something other than just drinks.

RS: After a while though I told my dad, “None of my friends want to come down to this south side biker bar. We need to change it up a bit.” So I came on a few years ago and kind of just brought what I loved in a bar: craft beer & sports.

Milwaukee didn’t have a real hockey fan bar, and I’ve played since I was 4. Our first viewing party for a Blackhawks game we probably had 3 people here and I was one of them. But the last Nashville Predators game was wall-to-wall people, and we’re a sponsor for the Admirals. We get players and coaches in here all the time. 

NHL rivalries can get heated.

TSC: What’s your favorite thing to do in Milwaukee?

JS: Eating, which is pretty easy to do around Walker’s Point now. I’m not a bar guy. If I’m not here (at Steny’s), I’m probably drinking at home. 

TSC: What are you drinking right now?

RS: It’s always something different. I’m a craft beer guy, and we’ve got 28 on tap at any time. Today it’s Milwaukee Brewing Company‘s Grapefruit IPA. I started working at Beechwood distribution out of school, learned a lot about craft beers, and brought that knowledge here to swap out a mostly macro lineup. 

JS: I don’t really drink much anymore. This hasn’t got anything in it (he was drinking a Michelob Ultra from a bottle)

RS: He usually’ll have a taster glass of one of my craft beers now, though. Jerry lives out in Muskego, so he’s gotta drive home from the bar.

Their outdoor beer garden has recently been converted into a 3-seasons porch. Watch for skeeball leagues to form this fall.

TSC: If you could have a drink with one other local celebrity, who would it be?

RS: I’ve met Aaron Rodgers twice, and he’s just the nicest, real guy you’ve ever met. I’d like to meet him again. 

JS: Maybe Robin Yount. But really, I’d rather have a drink with you, a normal person hanging out at Steny’s.

TSC: What’s Steny’s most popular drink nowadays?

JS: Our Bloody Mary hasn’t changed in 32 years, since day 1. My wife, Cheryl, and I put together our recipes from our past jobs and created something new back in ’85. And you can get a chaser of anything we have on tap. It’s been voted best in Milwaukee for three years. (TSC note: you can even get a growler of it to go!)

RS: His is the Bloody Mary, but mine is the Steny Bomb. It’s just something I came up with after some trial and error, for people who want to have a good time, but it’s fruity and a nice drink too. I love when people come in and order something I came up with.

TSC: If you could say one thing to someone just moving to Milwaukee today…

JSSummerfest is just amazing. We have the World’s Largest Music Festival just down the street. 

RS: How about, “Come to Steny’s and take our shuttle to Summerfest.”

TSC: How did you get your catchphrase, “You Should Be Here”?

JS: There was a bartender working here back somewhere between 1990, 95. I wasn’t working that night and I call into the bar and he picks up the phone and says, “This is Steny’s, you should be here.” Turns out he’d been saying that to people on the phone for a while, just came up with it. But it fits so perfectly. You really should be here.

Steny’s is open 7 days a week, so you can get your best-in-Milwaukee Bloodies whenever the fancy hits. And don’t miss their free shuttles to just about every gosh darn event in town.

In Milwaukee’s most up-and-coming neighborhood, there’s arguably no more established and influential joint than Steny’s Tavern & Grill. Stop in when you’re in Walker’s Point, and tell Ryan or Mayor Jerry that The Curd sent you. I’m sure they’ll have a beer and a story or two for you.

The Stenys and The Squeaky Curds!

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