Going to the hip, new place is definitely cool. But what’s equally cool is going to be a place that’s just been there forever. Wisconsin has a lot of those places–the places that have that weathered look but are full of character. Here are seven of our very favorites:

  1. Koz’s Mini Bowl

Koz’s Mini Bowl/Facebook Unless you’re from the East Coast–and maybe that even isn’t a definite anymore–you’ll have no idea what duck pins are. Duck pin bowling is not the same as the traditional bowling you’d find in a regular bowling alley. The pins are much shorter and squat. And you don’t stick your fingers in the bowling balls. It is entirely different, but a lot of fun, and probably more challenging. But besides bowling, you can also drink. It’s a great crowd, and it’s definitely a unique bar. Where else would Koz’s be a mainstay but Milwaukee?

  1. Skyway Drive-In Theatre

Skyway Drive-In Theatre/Facebook Sadly, there are very few drive-ins anymore, and a lot of kids don’t even know what the concept is. Drive-ins are a great part of summer, and Skyway is a great one to hit up if you are in the Door County area. Skyway opened their gates way back in 1950, and while the drive-in theatre has undergone some work, it still retains that 1950s vibe. You’ll really get a charge out of the cartoon advertisements they show–way back from the past, yet you’ll know them.

  1. Frank’s Diner

Frank’s Diner/Facebook So, let’s talk about old school. Frank’s has been around since 1926. There’s nothing flashy or fancy about this place, and they’re not apologizing. And there’s no reason to apologize, because the food is great and the character is one-of-a-kind. It’s a Kenosha landmark, but people from all over drive out of their way to go to Frank’s. Finally, the people over at Food Network took notice, and Frank’s was featured on an episode of Diners, Drive-Ins and Dives. Get a juicy burger or a big breakfast. Oh, and bring cash, because they’re cash only.

  1. Ardy and Ed’s Drive In

Ardy and Ed’s Drive In/Facebook So if you have a Sonic by you, you have some idea of the concept of a drive in. But do not even compare Sonic to Ardy and Ed’s. It isn’t even a close race. There is nothing corporate about this Oshkosh joint–just classic drive-in fare with excellent customer service. And yes, the carhops are on skates. It is an authentic 1950s restaurant, and you still definitely get that feel. Get your fill of hamburgers and root beer floats.

  1. Leon’s Frozen Custard

Leon’s Frozen Custard/Facebook Frozen custard is really, really serious business in Wisconsin. Everyone has their favorite. But Leon’s has been in the conversation since 1942, when they opened. Although they are a Milwaukee landmark, people travel from far outside Milwaukee to sample Leon’s Frozen Custard. And once you taste their custard, it is very easy to see why. Each day, they serve vanilla, chocolate, and butter pecan, as well as a special flavor of the day.

  1. Aftershock Retrogames

Aftershock Retrogames/Facebook Not technically a vintage business itself, Aftershock Retrogames offers a classic arcade experience. Look around you: all of the arcades are closing. There used to be one in pretty much every town and there just are not anymore. What’s great about Aftershock is that not only do they have all the games you would possibly want to play, but they also have pizza. Because gaming makes you hungry! And the pizza is good. Head down to Monona and step back in time.

  1. Bryant’s

ljiphotography/Flickr Located in Milwaukee, Bryant’s has been in operation since 1938. It is Milwaukee’s oldest cocktail lounge. It definitely has that vintage 1960s feel, though, and they totally embrace it with Mad Men Halloween parties for six years running. Tuesday-Thursday, they serve Depression-era cocktails, further capitalizing on that vintage feel. But don’t let the fact that this place is old fool you. You’ll be lucky to get a seat. There are no reservations and the place is guaranteed to be packed. Oh, and these bartenders actually know what they’re doing. If you’re willing to try new things, they are going to introduce you to flavor combinations that you never imagined. It is a real treat, and many people call this their favorite bar in Wisconsin.

Where are your favorite retro Wisconsin hangouts? Let us know in the comments.

Koz’s Mini Bowl/Facebook

Unless you’re from the East Coast–and maybe that even isn’t a definite anymore–you’ll have no idea what duck pins are. Duck pin bowling is not the same as the traditional bowling you’d find in a regular bowling alley. The pins are much shorter and squat. And you don’t stick your fingers in the bowling balls. It is entirely different, but a lot of fun, and probably more challenging. But besides bowling, you can also drink. It’s a great crowd, and it’s definitely a unique bar. Where else would Koz’s be a mainstay but Milwaukee?

Skyway Drive-In Theatre/Facebook

Sadly, there are very few drive-ins anymore, and a lot of kids don’t even know what the concept is. Drive-ins are a great part of summer, and Skyway is a great one to hit up if you are in the Door County area. Skyway opened their gates way back in 1950, and while the drive-in theatre has undergone some work, it still retains that 1950s vibe. You’ll really get a charge out of the cartoon advertisements they show–way back from the past, yet you’ll know them.

Frank’s Diner/Facebook

So, let’s talk about old school. Frank’s has been around since 1926. There’s nothing flashy or fancy about this place, and they’re not apologizing. And there’s no reason to apologize, because the food is great and the character is one-of-a-kind. It’s a Kenosha landmark, but people from all over drive out of their way to go to Frank’s. Finally, the people over at Food Network took notice, and Frank’s was featured on an episode of Diners, Drive-Ins and Dives. Get a juicy burger or a big breakfast. Oh, and bring cash, because they’re cash only.

Ardy and Ed’s Drive In/Facebook

So if you have a Sonic by you, you have some idea of the concept of a drive in. But do not even compare Sonic to Ardy and Ed’s. It isn’t even a close race. There is nothing corporate about this Oshkosh joint–just classic drive-in fare with excellent customer service. And yes, the carhops are on skates. It is an authentic 1950s restaurant, and you still definitely get that feel. Get your fill of hamburgers and root beer floats.

Leon’s Frozen Custard/Facebook

Frozen custard is really, really serious business in Wisconsin. Everyone has their favorite. But Leon’s has been in the conversation since 1942, when they opened. Although they are a Milwaukee landmark, people travel from far outside Milwaukee to sample Leon’s Frozen Custard. And once you taste their custard, it is very easy to see why. Each day, they serve vanilla, chocolate, and butter pecan, as well as a special flavor of the day.

Aftershock Retrogames/Facebook

Not technically a vintage business itself, Aftershock Retrogames offers a classic arcade experience. Look around you: all of the arcades are closing. There used to be one in pretty much every town and there just are not anymore. What’s great about Aftershock is that not only do they have all the games you would possibly want to play, but they also have pizza. Because gaming makes you hungry! And the pizza is good. Head down to Monona and step back in time.

ljiphotography/Flickr

Located in Milwaukee, Bryant’s has been in operation since 1938. It is Milwaukee’s oldest cocktail lounge. It definitely has that vintage 1960s feel, though, and they totally embrace it with Mad Men Halloween parties for six years running. Tuesday-Thursday, they serve Depression-era cocktails, further capitalizing on that vintage feel. But don’t let the fact that this place is old fool you. You’ll be lucky to get a seat. There are no reservations and the place is guaranteed to be packed. Oh, and these bartenders actually know what they’re doing. If you’re willing to try new things, they are going to introduce you to flavor combinations that you never imagined. It is a real treat, and many people call this their favorite bar in Wisconsin.

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