Charleston: The Ultimate Local's Guide
Est. 1975 | Juneau Town
Downtown watering hole that actually feels like a neighborhood tavern
Do people ever fall for the old clever bar name trick anymore? We can’t imagine “I’m heading to My Office” works on anyone anymore, especially when it’s 6:30pm on a Friday. The name still warrants charm, since it’s a corner tavern stuck into the middle of Downtown. If you’re afraid of the flying Dracula from some bygone Halloween inside, then sip your beer outside on the quasi-patio window ledge bar. Many a beer have been chugged here before heading home after work.
Est. 1972 | Brown Deer
Bright, relaxed golf bar with cheap burgers
Across from Brown Deer Park, Rollie's is the kind of place where the regulars have been coming for decades, and while they'll eye you up and down when you walk in, they'll also chat you up and buy you a drink when they find out you grew up three blocks from their cousin. There's a small food menu, and everything is made right behind the bar by your bartender, so try not to order food when it's super-busy -- or during a Packers game, when the kitchen is closed, but there may be a spread of free food available. The dirt-cheap burgers are great, but the old-school fried smelt is the sleeper hit.
Est. 1985 | Riverwest
Friendly bar with roaming dogs and a jukebox
Don’t let the fact that you have to be buzzed into the front door by the bartender distract you -- it's because of some previous robberies, not because this is an exclusive club. Once you’re in though, you’re family. Bartender Connie has been there almost as long as Randy, the owner, some 30+ years, and there’s a few lazy beagles roaming around to pet. It’s a common occurrence that a nice regular at the bar will buy everyone a round in the form of business card-like free-drink coupons. Don't be surprised if there's free food when you show up, either.
Est. 1984 | Harbor View
Popular stop for peddle taverns with a serenading owner
The George of George’s Pub is a retired veteran and country music singer. His band, the Nashville Rejects, played the State Fair, festivals, and weddings regularly, and memorabilia from the band is all around the pub. If you’re lucky enough to go to George’s while he’s working the bar, be sure to ask for a serenade. He’s been known to belt out "Ring of Fire" on request with his gravely Cash-like voice. Failing that, darts, free popcorn, and NASCAR-themed crap on the walls are the entertainment of choice.
Est. 1945 | Riverwest
Fraternal organization's bar and bowling alley
Milwaukeeans unabashedly love bowling, and there is a number of taverns with old bowling alleys in the city. The six lanes in the basement of Falcon Bowl date to 1913, but the building is even older. This is the home of Nest 725 of the Polish Falcons, a fraternal organization that we can only assume is like the Freemasons, but with way more vodka. If you’re Polish in Milwaukee (highly likely,) then get your dupa in here and bowl while you enjoy some obscure Polish booze.
Est. 1978 | Historic Mitchell Street
Charming, wood-paneled duckpin bowling alley
Yep, another bowling alley, but this one’s mini. It’s called duckpin: The balls fit in your hand and the lanes are half the size of a normal lane. That means anyone can bowl, even if you’ve had far too many Busch cans. Those little pins really go flying, so don’t forget to tip your pinsetter. You don’t have to bowl while you’re at this tavern, but you’d be foolish not to. Make sure you call to reserve your lane ahead of time since this place can be hoppin' on the weekends with parties.
Est. 1908 | Lower East Side
Famous East Side classic
Wolski’s is like Wall Drug: You see bumper stickers about it everywhere. If you stay until closing on any night, you get a coveted bumper sticker that reads “I closed Wolski’s.” The stickers get stuck everywhere for a low-cost, genius marketing campaign. They are the fanciest spot on this list with a website and a nice patio now, but the dangerous steel tip darts and free popcorn remain, so it's impossible not to love them.
Est. 1908 | Forest Home Hills
South Side tavern with historic basement bowling
Holler House has the oldest certified bowling alley in the US, dating to 1908. The pins are still set by actual human beings, generally local kids, and you call ahead if you want to bowl so they can get a pinsetter for you. There are also bras hanging from the ceiling, because tradition (and local treasure, second-generation owner Marcy Skowronski) states that you remove and sign your bra on your first visit. Its fate was in jeopardy in 2013, however, when an inspector deemed the bras a fire hazard. The local alderman pulled some strings though, the bras were put back up, and all was right with the world once again. Don't ask for anything more complicated than an old fashioned, and don't order a draft beer -- there are none.
Est. 2014 | West Allis
Wrestling bar with insane drink specials
The newest bar on this list, the Drunk Uncle is also the most 'Stallis, even after a recent renovation made them much more updated than they used to be. Despite the shiny new coolers and backlit Jim Beam, it still feels like a dive bar, and that's the most important thing. When there's no Packers or Brewers games, wrestling is what you'll see on TV here, and on the wall art, and on the calendar, and on the owner's T-shirt... You get the idea. It's also pretty difficult to spend much money here, with specials like $2 everything on Sundays and $1 IPA Saturdays. That alone earns it the title of dive bar.
Est. 1980 | Walker's Point
Eccentric, lovable bar run by an owner of the same description
Don’t come to Art’s if you’re looking to be alone. Art won’t let that happen. As soon as someone walks in the door of his ramshackle little shack, he’s welcoming you and regaling you with tales of his old Buick or inviting you to play dice with the regulars (who will hate me for including Art's in this list again -- sorry guys). There’s a small kitchen and a few cheap specials like burgers and the fish fry, but the pizza is the best, especially when Art decides it's time for free pizza for all.
Est. 1970 | Lower East Side
Quintessential, homey East Side dive
All holiday decorations stay up year-round at Y-Not II because it’s just easier to leave them up. There’s always free popcorn, and lots of nooks and ramshackle booths to eat it in. That bar next door that you spied from the sidewalk on the way in? That’s the same place too, but it’s the morning bar, and only open in the mornings. Therefore, they’re open just about as much as they legally can be.
Est. 2007 | Burnham Park
New iteration of an old Polish concertina bar
Kochanski’s is a beautiful mashup of the old Polish neighborhood and rock music. Its two stages regularly feature Polish polka bands, rockabilly, bluegrass, and rock, sometimes dueling on both stages at once. Looking for an obscure Polish beer? You can get it here. And any potential thieves: don’t burgle here. Owner Andy Kochanski shot and killed the last armed intruder, and was supported by the cops and the neighborhood. Hardcore.
Est. 1884 | Riverwest
Quirky, no-frills pre-Prohibition tavern
The oldest continuously running tavern in the city, Uptowner opened in 1884. There weren’t any pinball machines back then, but it’s always served as the “home of the beautiful people,” a tongue-in-cheek self-descriptor. Anything this old is quirky, and Uptowner is no exception. Stuff on the walls regularly disappears and reappears once the thief regrets his decision to take a memento, and the hand-washing sink is located outside the actual bathrooms. Plus it opens in the morning, because day drinking.
Est. 1931 | Bay View
Unassuming corner tavern with a resident English bulldog
The long mural of socialites in very fancy tuxes and feather boas along one wall of The Newport really does not reflect the bar's clientele at all, unless you count the times when wedding parties show up in their party buses to do a little celebrating before the reception. This corner building held a "soda parlor" since before Prohibition ended, and it's probably a good guess that they were doing a little rum running. Nowadays, it's a chill spot to grab a stiff mixed drink, rip open a few pull tabs, pet the bar's resident dog, Patch, and order a frozen pizza and pitcher deal.