By Lori Fredrich Senior Writer & Dining Editor Published Oct 21, 2021 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!

Looking for new spots to try? Lori Fredrich will be dishing out her top five picks in 20 different dining categories throughout the month of October.  

What’s a dining 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. Leon's Frozen Custard

Leon's custardX

3131 S. 27th St., (414) 383-1784

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Frozen custard is ubiquitous in Milwaukee. And yes, you have choices. I grew up making regular stops at Kopp’s with my family, so they are definitely my nostalgic pick. But if you want an old school drive-in custard experience in the city, there’s no place like Leon’s. Despite a (very) small menu of food items, this stand is nearly entirely about the custard, which is available by the cup or cone (or in sundaes or shakes, of course). And, unlike other custard stands, which have gone wild with add-ins like truffles, cake, ripples and swirls), Leon's has stuck solidly to the basics. Daily flavors include vanilla, chocolate, butter pecan and a flavor of the day (strawberry, raspberry, mint, maple nut, cinnamon and their newest addition, Blue Moon). It doesn’t really matter which flavor you choose. Every cone is filled with simple, old fashioned bliss.

2. 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 60 years in business, Ashley's remains a community staple, providing busy families convenient weeknight carry-out and Sunday family meals.

3. Three Brothers

Three Brothers burek
Burek from Three Brothers

2414 S. St. Clair St., (414) 481-7530
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For 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.

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. Kegel’s Inn

The Mullers performing at Kegel's InnX

5901 W. National Ave., West Allis (414) 257-9999
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Among the things gradually fading from the Milwaukee landscape is its German cuisine. If losses like the 100-plus year old Karl Razsch restaurant taught us anything it’s that changing tastes and values have made it difficult for traditional venues to survive. But one of the places that’s keeping the spirit of Milwaukee’s Germanic heritage alive is Kegel’s Inn. Maybe most telling is that they’ve done it in a way that has simultaneously straddled the space between maintaining tradition and surviving. 

From the addition of a modern outdoor beer garden to an extensive kitchen remodel and a return to scratch-made German fare, they’ve committed to remaining relevant, even in 2021. And they’ve done so by connecting with the community, educating them with events – including their Muller Fasching Verien Nordamerika dinners and Oktoberfest – and moving ahead with their eyes open, even as they inch closer to their centennial.

Lori Fredrich Senior Writer & Dining Editor

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.