By Lori Fredrich Senior Food Writer, Dining Editor, Podcast Host Published Oct 08, 2022 at 10:02 AM

’Tis Dining Month, the tastiest time of year! This means we’re dishing up fun and fascinating food content throughout October. Dig in, Milwaukee! OnMilwaukee Dining Month is served up by Potawatomi Hotel & Casino and Wollersheim Winery & Distillery.

Looking for new spots to try? Lori Fredrich has dished out her top five picks in 20 different dining categories, from brunch to BBQ and everything in between. 

What’s a Milwaukee institution? It's nearly always a place that has a long history. It’s a venue where memories have been made (and continue to be made). It’s a spot that’s beloved (and sometimes polarizing), but which adds a certain “je ne sais quoi” to the landscape. It’s a venue which helps to define what Milwaukee was, what it is and what it’s becoming.

Yes, there are absolutely more than five such places in greater Milwaukee. But if you’re looking for a taste of some of the spots that have shaped the city and surrounding area (and keep them around for another 50 or 100 years), consider a visit to any one of these a good place to start.

1. Nite Owl Drive-In

Burger, fries and malt at Nite OwlX

830 E. Layton Ave., (414) 483-2524
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The drive-in restaurant is a dying breed. Born in the mid-twenties following the automobile boom, the drive-up restaurants saw their heyday in the 1950s and '60s before gradually losing steam to the newfangled drive-thru restaurants. 

But thanks to the diligence of Chris Roepke, the third generation owner of Nite Owl Drive-in, our city can continue to to relish the joy of this seasonal drive-up which has been serving up burgers, ice cream, malts and shakes since 1948.  Be sure to listen to our FoodCrush Podcast with Roepke during which he talks about the drive-in's history and the reason why they run out of burgers most days of the week.

2. Three Brothers

Three Brothers burek
Burek from Three Brothers

2414 S. St. Clair St., (414) 481-7530
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For over 65 years, the James Beard Award-winning Three Brothers restaurant has been serving up not only delicious, comforting Serbian fare, but a level of hospitality that few other restaurants can rival. This family-owned restaurant was birthed of necessity; but its legacy has become one of love, family and tradition that has been carried through three generations.

You need little more than to listen to Patricia and Milunka Radecevic talk about their beloved family restaurant to understand why Three Brothers is such a special place. And you need nothing more than to taste their spectacularly comforting Serbian fare, to realize that the restaurant is one we can’t afford to lose.

3. Ashley's Bar-B-Que

Plate of barbeque from Ashley's Bar-B-QueX

1501 W Center St., (414) 372-7666

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Founded in 1961 by former A. O. Smith employee Thomas Ashley, Ashley’s Bar-B-Que started out at a location near Haymarket Square before moving to 34th Street and then to the restaurant’s current location on Center Street. Today, the award-winning barbeque eatery is operated by second-generation owner and pit-master, Darnell Ashley, who carries on the family business with the same passion as his father. 

Like every BBQ joint, Ashley’s has its own distinctive style. Each of their smoked meats are treated to both a wet and dry rub before being slow-smoked in an old-fashioned pit barbecue with wood and charcoal until they're smoky, and tender.  Best of all, even after 61 years in business, Ashley's remains a community staple, providing busy families convenient weeknight carry-out and Sunday family meals.

4. Real Chili

Real Chili signX

419 E. Wells St., (414) 271-4042
1625 W. Wells St., (414) 342-6955

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If one didn’t know better, they might mistake Real Chili’s offerings as a derivation of the “Cincinnati style”. But no. Real Chili has its roots solidly in Wisconsin and its recipe predates the Ohio-style chili by over two decades. The first Real Chili opened in Milwaukee in 1931 when Francis Honesh brought the recipe from Chili John’s in Green Bay (established in 1910) and set up shop in the basement of the Jesuit rectory on the campus of Marquette University.

Today, there are two locations (both on opposite sides of Wells Street), each sporting a back-to-basics old school diner feel. And if you want to experience exactly how ingrained the fast-casual chili shop is, just take a seat and place your order for the off-menu “Marquette Special” (a bowl of medium-spiced chili with spaghetti and beans).

 5. Usinger's Famous Sausage


1030 N. Dr. Martin Luther King Jr. Dr.,  (414) 276-9100

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While not a restaurant, Usinger's has contributed to the food landscape in Milwaukee since 1880. And they have endured while remaining true to time-honored methods and recipes.

Flip over a package of Usinger’s braunschweiger and you’ll find a minimal list of ingredients: pork liver, pork, salt, beef, onions, spices.

That old fashioned, no frills ingredient list is a pride-point for the Milwaukee-based company, which has been producing a variety of traditional sausages and meat products for over 140 years.  Despite some modernization in their processes, Usinger's has remained true to tradition, honoring Frederick Usinger's original recipes and adhering to processes – including the use of old school European style smoking methods – to create quality, artisan-level products which are now shipped across the U.S.  

Lori Fredrich Senior Food Writer, Dining Editor, Podcast Host

Lori is an avid cook whose accrual of condiments and spices is rivaled only by her cookbook collection. Her passion for the culinary industry was birthed while balancing A&W root beer mugs as a teenage carhop, fed by insatiable curiosity and fueled by the people whose stories entwine with each and every dish. She’s had the privilege of chronicling these tales via numerous media, including OnMilwaukee and in her book “Milwaukee Food.” Her work has garnered journalism awards from entities including the Milwaukee Press Club. 

When she’s not eating, photographing food, writing or recording the FoodCrush podcast, you’ll find Lori seeking out adventures with her husband Paul, traveling, cooking, reading, learning, snuggling with her cats and looking for ways to make a difference.