In a city renowned for its rich cultural heritage and culinary history, Milwaukee is home to several historic restaurants that have stood the test of time. From the “the big three” custard stands that put Milwaukee on the map to the German restaurants that reflect the city’s early European settlers, these local gems offer much more than just a meal — they provide a taste of history.
Many have been in the same family for decades while others have been preserved by new owners who understand their cultural importance. They’re the restaurants where core memories are formed, tastes are developed and where multiple generations have sat down to share the same scoops, sandwiches and schnitzels for years.
From a 70-year-old charmer in Bay View to Wisconsin’s oldest restaurant with nearly 180 years of history, here are some classic Milwaukee restaurants that are still going strong.
KINGS OF MILWAUKEE CUSTARD
In a city dubbed as the unofficial “frozen custard capital of the world,” it’s no surprise Milwaukee boasts long-beloved classics that have been serving cool treats to locals and vistors for generations.
Gilles Frozen Custard, est. 1938
Gilles Frozen Custard, 7515 W. Blue Mound Road, is the city’s oldest custard stand at nearly 90 years old. Founded by Paul Gilles in 1938, the stand remained under his helm until 1978, when he sold it to Robert Linscott. Today, Robert’s son Tom operates the stand with his son, Willy. Though “frozen custard” takes top billing on the menu, the stand offers much more, including everything from burgers and hot dogs to a classic fish fry and grilled ham-and-cheese sandwiches.
Even if you’ve been visiting the classic custard stand your whole life, you still may be mispronouncing its name. Though many call it “Gill-eez,” the proper pronunciation is actually “Gill-us-es.” Good luck breaking that habit next time you’re there for a cone.
Leon’s Frozen Custard, est. 1942
On the city’s south side, Leon’s Frozen Custard came just a few years after Gilles, in 1942 (fun fact: Leon’s founder Ron Schnieder worked at Gilles before going into the custard business on his own). Known for its iconic 1950s-era design with glowing neon lights, the custard stand at 3131 S. 27th St. keeps things simple with just three daily flavors (vanilla, chocolate and butter pecan) and rotating flavors of the day (strawberry, raspberry, mint, maple walnut, cinnamon and Blue Moon).
It’s a beloved local hangout, but Leon’s lures in celebrity visitors, too, including musician Neil Diamond, “Everybody Loves Raymond” creator (and major foodie) Phil Rosenthal and the “Top Chef: Wisconsin” judges and crew while they filmed the show here in 2023.
Kopp’s Frozen Custard, est. 1950
Eight years after Leon’s opened its doors, another Milwaukee stalwart followed suit. Kopp’s Frozen Custard opened in 1950, founded by Elsa Kopp. It may have been the last of the big three to open, but Kopp’s is an innovator: it actually invented the concept of rotating flavors, introducing them in the 1960s before any others dared to venture beyond chocolate and vanilla. Now, you can sign up for emailed “flavor alerts” on Kopp’s website so you never miss your favorite flavor again.
Kopp’s was recently voted the favorite custard in town by Milwaukee Journal Sentinel readers. And in December 2025, Kopp’s grabbed attention again when Hugh Jackman, in town promoting his Milwaukee-set movie “Song Sung Blue,” drew an hours-long line at its Greenfield store, scooping free custard for adoring fans.
Kopp’s Frozen Custard has three Milwaukee-area locations: in Greenfield (7631 W. Layton Ave.), Glendale (5373 N. Port Washington Ave.) and Brookfield (18880 W. Blue Mound Road).
GERMAN GREATS
Mader’s Restaurant, est. 1902
With Milwaukee’s rich German heritage, it’s fitting that its oldest restaurant would be known for serving traditional German cuisine. Mader’s Restaurant has been open since 1902, when Bavarian-born Charles Mader opened his restaurant, then called The Comfort, on what is now Plankinton Avenue. The restaurant later moved to its current location at 1041 N. King Dr., and in 1950, the restaurant was expanded and renovated to give it the distinctive Germanic-hall appearance it has today.
Mader’s is filled with Old-World charm from the outside to the dining room, an ornate space with Bavarian decor and a waitstaff that dons dirndls and lederhosen. Specialties include the pork shank with apple demi-glace, sauerbraten served with spaetzle and lightly breaded wiener schnitzel, but modern twists like Reuben rolls made with wonton wrappers and beer cheese spread with pretzel crostini bring the beloved Bavarian restaurant into this century.
Kegel’s Inn, est. 1924
In West Allis, another German restaurant traces its roots back more than 100 years. Kegel’s Inn, 5901 W. National Ave., has been a fixture in the city since 1924, when John and Anna Kegel opened the business as Kegel’s Place. Today, it’s run by fourth-generation owner Julian Kegel and his wife, Stephanie.
The beer hall-style space features ornate, hand-painted murals and its original mahogany bar. It serves classic German fare like rouladen and schnitzels of all sorts, as well as loaded brats, sandwiches and snacks like currywurst, cheese curds and frites. It also has one of the area’s best Friday fish fries, serving perch, cod, bluegill, walleye, grouper, catfish and even a vegan fish fry.
Jack Pandl’s Whitefish Bay Inn, est. 1915
For more than 110 years, Jack Pandl’s Whitefish Bay Inn has been a cozy retreat at 1319 E. Henry Clay St., owned by the same family since its debut in 1915. Though not strictly a German restaurant, it serves traditional weiner schnitzel, spaetzle and its signature German pancakes alongside American classics like steaks, seafood, sandwiches and its weekly fish fry. From its large collection of beer steins and antlers in its bar to the colorful glow of the Tiffany lamps hanging through, Jack Pandl’s is still loaded with Old-World charm more than a century after opening its doors.
DINERS, DRIVE-INS AND DELIS
Solly’s Grille, est. 1936
Home to the original butter burger, Solly’s Grille, 4629 N. Port Washington Road, Glendale, has been a diner destination on Milwaukee’s north shore since 1936. It serves diner classics like farm-style breakfast platters, homemade pies and malts and shakes, but the butter burger is Solly’s claim to fame (Culver’s founder Craig Culver has acknowledged that Solly’s was the first to make the butter-brushed burger that his chain has popularized across the country).
Guests gather around two U-shaped diner counters, perched on the same swivel stools they’ve claimed for decades. Solly’s is beloved in Milwaukee, but it’s claimed national attention, too. It’s appeared on Food Network, the Travel Channel and, in 2022, was honored with the America’s Classic Award by the James Beard Foundation, awarded for the diner’s “timeless appeal” and food that “reflects the character of its community.”
The Nite Owl Drive-In, est. 1948
You know spring has officially arrived once the Nite Owl Drive-In, 830 E. Layton Ave., opens for business. Typically operating between late March and late October, the seasonal sandwich shop and ice cream parlor has been open on the south side since 1948 and is still a family-run operation. It operates pretty much as it did back then, too, making fresh burgers from its daily delivery of ground beef. Once that beef runs out, the restaurant closes — so if you have your heart set on a Nite Owl burger, it’s best to claim yours early.
Aside from its famous burgers, the Nite Owl also serves hot dogs, french fries, onion rings, a fish sandwich, ice cream, floats and sundaes. Just remember to bring cash — just as it was in 1948, it’s still a cash-only establishment.
Ma Fischer’s, est. 1932
Greasy-spoon stalwart Ma Fischer’s has been serving up skillets, omelets, pancakes, meatloaf, sandwiches and more since Jackie “Ma” Fischer opened her eatery at 2214 N. Farwell Ave. in 1932. Peter Panos bought the diner from Fischer in 1975, and it’s been run by the family since, always paying homage to the woman who started it all (you can’t miss the life-sized statue of “Ma” that now towers over the restaurant’s parking lot).
Once known as a 24-hour haven for the late-night (and extremely early-morning) crowd, Ma’s cut its hours back in recent years (now open from 7 a.m. to 9 p.m. daily), so it’s lost a bit of its luster as a refuge for nearby college students, second-shifters and anyone looking for a bite in the middle of the night. But it still has the same old-school charm: deep booths, classic counter seating overlooking the kitchen, and a massive menu of diner classics.
Ted’s Ice Cream & Restaurant, est. 1941
If you’re looking for retro vibes and family-friendly fare, Ted’s Ice Cream & Restaurant, 6204 W. North Ave., Wauwatosa, is your spot. The tiny diner opened in 1941 and is the sort of place you’d imagine Richie and the gang dropping into on “Happy Days.” Decked in a color scheme of cream and fire-engine red, the breakfast-and-lunch spot has two horseshoe-shaped counters that squiggle through the center of the room, lined in chrome-accented swivel stools with red padded seats.
Go for steaming mugs of coffee and omelets with crisp hashbrowns at breakfast, or bite into a juicy burger, Reuben sandwich, tuna melt or turkey club at lunch. And of course, you can’t skip dessert here. All of the ice cream is made in-house, with rotating flavors alongside vanilla and chocolate, plus a long list of sundaes, malts and shakes.
Jake’s Delicatessen, est. 1955
The pastrami sandwich at Jake’s Delicatessen is one of the city’s best sandwiches, and the restaurant’s fatty, tender corned beef is right up there with it. Those meaty handhelds have helped make Jake’s a dining destination since 1955, when the deli opened at 1634 W. North Ave., catering to Jewish families who lived nearby at the time.
Still in its original location, the restaurant was kept open for years thanks to former baseball commissioner Allan H. “Bud” Selig, who held an ownership stake in the business from 1969 to 2021. Today, patrons can order corned beef, pastrami and turkey sandwiches served on S. Rosen rye bread or order meat by the pound. Settle into one of the vintage, high-backed booths to eat, but before you do, nab a seat on the counter-side pew so you can catch the deli workers hand-slicing the meat fresh for each order.
CASUAL CLASSICS
Caradaro Club, est. 1945, and Zaffiro’s Pizza, est. 1954
Milwaukee is home to a handful of pizzerias that have been slinging pies for more than 60 years. We can’t dedicate this space to all of them, so we’ll focus on two of the first to make the city’s cracker-crust pizzas iconic.
On the west side, Caradaro Club claims it’s the first restaurant to serve pizza in Milwaukee, period. The restaurant originated in the Third Ward in 1945 (there’s a plaque there now commemorating the birthplace of pizza in Milwaukee) and its locations and owners have bounced around over the years, but there’s still a Caradaro Club restaurant at 5010 W. Vliet St.
Another cracker-crust favorite, Zaffiro’s, 1724 N. Farwell Ave., hasn’t moved an inch since it opened on the east side in 1954. Opened by Bobby and John Zaffiro, the restaurant is still family owned. It’s now run by Bobby’s son Michael and his wife, Rose, who serve classic Milwaukee-style pizza, pasta and other Italian favorites in the original tavern space and expanded dining room, which was added in 1970.
Real Chili, est. 1931
Speaking of crackers, you may catch oyster crackers whizzing by if you stop into Real Chili late at night amongst the buzz of the post-bar crowd. The circular crackers are one of the toppings for this Milwaukee institution’s signature bowls of beefy chili, a recipe Francis Hornish brought from Green Bay to his new restaurant on the Marquette University campus in 1931. (They’re also fodder for the late-night food fights that occasionally break out there.)
Today, Real Chili has two locations: the original at 1625 W. Wells St. and its downtown location blocks away at 419 E. Wells St. Both ooze with old-school charm and still ladle up the original-recipe chili served mild, medium or hot over spaghetti or hot dogs. From there, top it your way with options like shredded cheese, beans, jalapeños and onions.
DINING DESTINATIONS
Three Brothers, est. 1956
A cornerstone of Milwaukee’s Bay View neighborhood celebrates its 70th anniversary in 2026. Three Brothers, opened in 1956 by Milun and Milunka Radicevic, serves Serbian staples like tender sarma, fresh Serbian salad, rich musaka and flaky burek. In its 70-year run at 2414 S. Saint Clair St., the restaurant has never employed a chef outside of the Radicevic family, preserving the family-heirloom flavors that have kept customers coming back for decades.
The old-school charm inside the small restaurant recreates the feeling of dining in your grandmother’s kitchen, with bentwood chairs, mismatched dishes and big platters of rib-sticking dishes being passed around crowded tables. In 2002, Three Brothers received the America’s Classics Award from the James Beard Foundation, and all these years later, its name still appears on the Journal Sentinel’s annual list of Milwaukee’s Top Restaurants.
The Red Circle Inn, est. 1848
Wisconsin’s oldest restaurant is just a short drive from Milwaukee: The Red Circle Inn at N44 W33013 Watertown Plank Road in Nashotah. Originally known as the Nashotah Inn, the restaurant first opened its doors in 1848, making it older than many of the establishments on this list by over a century. In 1889, Frederick Pabst of the Pabst Brewing Co. bought the business and renamed it the Red Circle Inn. The original 1889 Pabst bar still stands proudly in the restaurant’s upstairs banquet area, serving as a reminder of the establishment’s rich history.
Now, the restaurant brings a modern twist to the classic Wisconsin supper club, serving steaks and comfort fare like chicken marsala, chicken pot pie, baby back ribs and braised beef stroganoff. A 2022 renovation has modernized the space, blending historical charm with contemporary dining tastes. Yet, through careful restoration, elements like Pabst’s bar and other relics have been preserved and restored to showcase the rich history of this tie to Wisconsin’s past.
As General Manager Kyle Johnson told the Journal Sentinel in 2025, “You could say the whole thing is kind of a little museum.”
This article originally appeared on Milwaukee Journal Sentinel: 16 iconic Milwaukee restaurants still going strong after 70-plus years
Reporting by Rachel Bernhard, Milwaukee Journal Sentinel / Milwaukee Journal Sentinel
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