Looking for new spots to try? During Dining Month, Lori Fredrich is dishing out must-tries in 20 different dining categories, from brunch to BBQ and everything in between. Here's what she's recommended so far!

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 four 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 30, 50 or 100 years), considering a visit to any one of these a good place to start.

Conejito's Place

539 W. Virginia St., (414) 278-9106
conejitosmke.com
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For over 50 years, Conejitos has been a South Side staple, perhaps best known for its cheap, tasty tacos (served up on paper plates), no-frills margaritas and the empty flower pots hanging from its ceiling.The restaurant has been cataloged among the most polarizing spots in the city; and yet there’s no denying that Conejitos was also among the pioneers of Mexican cuisine in Milwaukee. 

Late owner Jose Garza got his start with a small tavern on the 700 block of S. 6th St. where he served steak tacos as a courtesy for customers. In 1972, he moved his business to its current location on 6th and Virginia. Even then, the restaurant was among just a few spots in the area serving traditional Mexican fare.  

For 38 years, Garza (whose nickname was Conejito: "bunny" in Spanish) was the face of the bar and restaurant. He was also the man who donned an apron every Sunday to make the restaurant’s popular huevos rancheros, which were notable due to their poached (not fried) eggs and Garza’s special sauce.

Conejitos was always known for its affordable fare. In the  mid-70s Garza’s steak tacos (flour tortillas with slices of skirt steak, lettuce and tomato) were sold four to a plate for just $1.50. Today they’re still a steal at $6.50 and you can add a house margarita to the mix for just $4.50 more.

Even after Garza lost his battle with cancer in 2010, passing away at the age of 75, his memory has lived on in the form of photos, plaques and – maybe most of all – the friendly, welcoming atmosphere that he created.

In a 2008 OnMilwaukee interview, Garza said: "From day one, business has been good. It's always good because I have lots of power from above. Everyone who comes into Conejito's becomes my friend. They might first be a customer, but in time, they are a friend."

Five O’Clock Steakhouse

2416 W. State St., (414) 342-3553
fiveoclocksteakhouse.com
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1946 was also the year that a long-time State Street tavern, which had also operated for a short time as a bakery and – like numerous other bars – as a pharmacy during prohibition (selling ice cream, fountain drinks, “medicine” and cigars), shifted gears again, becoming one of the city’s best loved and longest running steakhouses: Five O’Clock Steakhouse. 

The Five O’Clock Club, which arose in the era of supper clubs, embraced its new identity at the hands of Wilmer "Bill" Coerper, who added his moniker to the name and expanded the footprint of the venue, creating the foundation for the steakhouse that exists today.

Over the course of its existence, Five O'Clock Steakhouse has weathered  11 economic recessions (both large and small), including three in the past two decades (2001, 2008-2009 and most recently 2020, a period which has been declared the worst recession since the Great Depression).

Today, the steakhouse’s legacy is carried on by Stelio Kalkounos, whose family purchased the business from the Coerpers in 2004 and passed full ownership to Kalkounos in 2017.

Among the keys to Five O’Clock’s longevity is its adherence to beloved supper club traditions from starting off the night with drinks (including hand-muddled old fashioneds) at the bar before being seated in the dining room, relish trays on the tables and live music. 

But offering up nostalgia alone doesn't keep the doors open. In Five O'Clock's case, the restaurant has also been adept at changing with the times, occasionally updating menu items to meet diners' expectations and using high-quality ingredients including beef cuts from Creekstone Farms Natural Black Angus and Meats by Linz and mushrooms, which are caramelized and cooked slowly in butter, from River Valley Ranch in Burlington, Wisconsin.

Reynold’s Pasty Shop

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3525 W. Burleigh St., (414) 444-4490
reynoldspasties.com
Before fast-casual spots were all the rage, there was Reynold’s Pasty Shop, a storefront on Burleigh that has been serving up hand-made pasties to a loyal audience since 1956.

But what’s a pasty?  First, the name is pronounced /pass-tee/ are said to have origins as the original “fast food” of copper miners and lumberjacks. Brought to the Upper Penninsula and Northern Wisconsin by Cornish immigrants, the meat pies were an all-in-one lunch solution for minors who’d take the easy-to-transport handheld pastries into the mines as their daily sustenance. And while Milwaukee may be short on lumberjacks and copper miners, the hand pies still serve the same noble purpose: offering a full meal in a small, transportable package.

Reynold’s pasties, which are still handmade daily with a recipe that’s been passed down through the generations (and owners), feature a crisp dough stuffed with fresh carrots, potatoes, onions and minced beef. Since they’re hand-formed, each pie has its own charmingly irregular shape. At the shop, hot pasties are available hot, par-baked or frozen with add-ons like brown gravy, sour cream, cheese and jalapeños. 

Pop into the shop on any given day and and you're likely to find a line of loyal regulars at the register. In fact, trips to the local pasty shop are a time honored tradition for many who grew up enjoying the locally-made pastries with their parents or grandparents.

“I’ve been coming here since I was in grade school,” one woman at the shop noted as she waited in line for her pasty on my latest visit. “And even now, when the craving for a pasty hits, you just have to have one.”

Sanford

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1547 N. Jackson St., (414) 276-9608
sanfordrestaurant.com
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These days it’s tough for a restaurant to make it five years, let alone 30 or more. And yet, Milwaukee is home to a number of restaurants that have not only stood the test of time but remained relevant despite an increasingly challenging landscape. Among them is Sanford, a staple fine dining spot that (quite literally) helped to put Milwaukee on the national dining map.

Founded by Sanford D’Amato in 1989, Sanford has been honored with countless accolades, including a nod as Best New Restaurant by “Esquire” magazine in 1990 and a slot on  “Gourmet” magazine’s 50 Best Restaurants list. Even more, in 1996 D’Amato was the first Wisconsin chef to bring home a James Beard Award in the category of Best Chef Midwest.

The restaurant has continued to thrive under the ownership of Chef Justin Aprahamian and his wife Sara, who took the reins at Sanford in 2012. Under their purview, the restaurant has continued to offer top-notch cuisine and service even through the global pandemic when they pivoted to carry-out, allowing customers new and old to enjoy expertly prepared food in the comfort of their own homes. 

Over the years, as Milwaukee has become a city recognized for its food scene, James Beard Award-winning chef and co-owner Justin Aprahamian has continued to approach his work with humble fervor, ensuring that Sanford’s ever-changing menu of globally inspired seasonal New American fare has remained relevant and (more importantly) delicious. Meanwhile, under Sara’s guidance, the restaurant’s hospitality has remained as cordial as ever, ensuring that the guest experience is excellent from start to finish.

Thirty-four years after opening – despite national trends that favor more casual dining concepts – the Aprahamians have proven that there is still a place, and an appreciation, for finer dining in the Milwaukee landscape.