Every town, city or neighborhood has a place that you drive past day after day and think: What’s that place’s deal? It’s a spot that you’ve driven past and easily recognize but somehow have never actually entered. A deep-rooted community mainstay yet never a regular topic pushing for attention, simultaneously essential and invisible like oxygen. You’d be shocked to see such an everyday staple close, but also – with the constantly changing times, expectations and clientele – shocked that such a trend-defiant relic is still open. 

Everywhere has that spot – and for me, growing up in Hales Corners, that was Annie’s Place. And apparently I’m not alone.

“Everybody when they come in here for the first time, everyone says, ‘I drive by and I never stop in here.’ And then they do, and they say it’s like being up north,” said Scott Lessmann, a Annie’s Place customer since its opening in the '80s and an occasional bartender for more than two decades.

Found at 10432 W. Forest Home Ave., the timeless tavern isn’t hard to find, located on one of the village’s main drags tucked between Clifford’s – home to one of the area’s most famous fish fries – and a popular grocery store plus down the street from all sorts of local hangouts and essentials. Prime placement, however, can be a blessing and a curse. Annie’s always seemed the place you’d see along the way to your destination, rarely the destination. 

So … what’s that place’s deal? 

After decades of asking that question, it was my turn to solve this tan, time-tested mystery sitting in plain sight for myself. And it turns out Annie’s Place’s deal is that it’s delightful, a deeply frill-free but also deeply friendly neighborhood tap and hangout that earns the “Cheers” theme song references it inevitably inspires. Annie’s is indeed the kind of place where everybody knows everybody’s name and has a story to tell – and if you don’t, you soon will on both accords.

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A sign out front of Annie’s Place, just to the right of the front door, briefly tells the history of the building, putting its foundation down all the way back in 1900 and placing it alongside The Bosch Tavern among historic Hales Corners landmarks going back to the village’s origins. Throughout the years, the spot mostly served as a tavern and pitstop – and, if you believe the regulars, a brothel in its earliest days with the help of a sneaky back stairwell. However, it didn’t become Annie’s Place until 1988 when the titular Annie Callahan took over the tavern.  

"My mother lived in Kenosha at the time and moved down here by herself and started the business by herself 35 years ago,” said Patrick Callahan, Annie’s son and the spot’s regular bartender. “My cousin found the place cheap and for sale, and she bought it, fixed it up and been in business ever since.”

“Annie was just always really good to us, so we always just kept coming back,” said longtime customer Tony Riva. 

The regulars joke Annie’s Place hasn’t changed much since then – and indeed, the watering hole is low on flash or finesse but high on classic neighborhood dive character. A side room is packed with bar games – popular with many of the regular patrons – while lights, local sports gear and bar signs old and less old charmingly clutter most of the walls alongside some holiday décor. A number of Little Orphan Annie references can be found peppered around the space as well, in homage to the bar’s now 82-year-old owner – whose photo cutout can be found smilingly flashing a one-finger salute in the window. 

"She's like everybody's mother. She's like the community mother," added Paul Wnuczek, a 15-year regular of Annie's Place. 

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The rest of the family decorates Annie’s Place as well. A large image of the whole Callahan clan smiles down from above the bar, while behind the bar and above the register, a photo pays tribute to Patrick’s sister Veronica, who sadly passed away almost a decade ago due to lung cancer. 

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Indeed, you can feel the family fingerprint at Annie’s Place – a welcoming vibe that extends beyond just the Callahans. You don’t need to be distracted by modern bells and whistles because there will be plenty of conversation to be had – especially if Patrick is tending bar, playing host. Sure, there’s a pool table that hosts some regular competitions – but the entertainment is the engaging people in the stools. Everyone seems to know everyone inside Annie’s Place, all regulars for at least a decade and all sharing stories and jokes about the neighborhood and the latest bar drama and gossip. And they all share the same reason why they come back time and time, happy hour after happy hour. 

“This is where you’re going to find good conversation and genuine, down-to-earth people,” Callahan said.

“You know, it’s just a nice place,” said Tom VanRemmen, a longtime Annie’s patron. “It’s a community center where friends gather. You come here on certain days, you’ll find a lot of tradespeople who stop in here. On the weekends, you’ll find a variety of people – even bar owners from other bars around the area.” (Indeed, Annie's seems like your favorite bar's favorite bar judging by the amount of fellow tavern owners dropping in.)

“It just brings the whole community together – to watch sports or whatever,” said Paul Kharoum, another local regular.

Of course, the prices nicely contribute help too. Inflation must’ve made the mistake of driving past Annie’s Place without stopping in as well, because the menu is $3 for anything and everything – a selection including Miller High Life, MGD, Pabst Blue Ribbon and other macro favorites and tap classics. (Note: It’s cash only, so come prepared ... or at least prepared to use the in-house ATM.) The bar also offers a selection of Emil’s frozen pizzas to help soak up the suds as well as the occasional crockpot of home-cooked food for holidays, big games and parties. One patron even claimed Annie’s Swedish meatballs are the best you’ve ever tasted – though unfortunately she's now retired from cooking. But overall most Annie’s Place customers seem content to dine on a pork chop in every can. 

After all, the food isn’t why anyone stops into Annie’s Place. Much has changed over time, but Annie’s has stayed the same and so has its appeal: a comfortable neighborhood tap where you instantly feel like a neighbor no matter if you live across the street or all the way across town.  

“It’s been here for so long, and it’s just a fun place to go to. Very, very friendly. Patrick, when you walk in, he’ll introduce you to everybody. That’s a good bartender,” VanRemmen said.

So learn from me and many others before: Next time you’re driving past that bar that has you asking “what’s the deal with that place?” stop asking that question and actually go in and find out. As Annie's Place taught me, you might just love the answer.