A Whirlwind Tour of Historic Boston Bars

A few months ago, President Obama stopped by Boston's Union Oyster House for chowder. Being a tourist with few original thoughts of my own, I decide to follow suit and find myself perched at the very same raw bar. I order a beer, a cup of chowder, and three fat oysters.

The Oyster House has been in the shucking business since 1826. According to its brochure, the place is America's oldest restaurant in continuous service. JFK even had a favorite booth there. Considering the bar's high-profile clientele and history, I figured that it had to be a classic tourist trap. I dip into my chowder and eavesdrop on the other guests, but hear nothing but Boston accents dominating the chatter.

There are really locals here?

"It depends on the time of the year. Right now it's about 90 percent local," Charles White—better known as "Whitey"—explains of the clientele at The Green Dragon Tavern, a bar two doors down from Union Oyster House. Spring and summer bring hoards of visitors to Boston, but it's all quiet on the tourism front during the harsh winter.

"We have so many regulars, you can't even keep track of them," Whitey says.

I look around at the cozy bar. There's a lot of dark wood, old-timey lanterns, antiquated maps of Boston. There are some lingering Christmas decorations hanging around. I ask what brings locals to kitschy places like The Green Dragon Tavern.

"It has historic value. They planned the Boston Tea Party drinking at the Tavern. It stands out from most other places," Whitey says. "You have the Bell in Hand Tavern, Union Oyster House. These are the oldest places. It's definitely unique."

Whitey's worked on this block for nearly two decades. Before he ended up at his current post, he spent seven years at Union Oyster House. From his perspective, he doesn't care whether a client is a local or a tourist.

"You're either cool or you're an asshole. It doesn't matter where you're from. People are people. Most of them are really nice," he says. "I'm not going to be the guy who says, 'I don't like tourists,' because I go on vacation and I want to be treated nice, too."

Before I head back out into the bitter Boston cold, I ask Whitey if he believes in beer jackets.

"No. I've been pretty hammered and still been cold," he tells me. "I mean, if you do a shot of whiskey, you're going to get that tingle up your spine and your face will feel hot, but five minutes later you're just drunk again."

Bummer.

I head to the nearby Bell in Hand Tavern and take a seat at the bar in front of a TV. There's a Boston Celtics game on (because of course there is). I look around at the 18th-century portraits surrounding the dance floor where a band is setting up gear.

The place feels more like an Applebee's than the other 200-year-old institutions I'd seen, but the crowd is definitely from around town. There's a holiday party going on upstairs, and buzzed coworkers occasionally lumber down to check out the ground floor. Justin Bieber plays overhead and the menu offers a raw kale salad and root fries with wasabi sauce. I drink a malty Newcastle and talk to a local cartoonist about his dreams of making it into The New Yorker.

I get an Uber and head to the Bunker Hill Monument in Charlestown just across the river from downtown Boston. It's 6 PM and 25 degrees outside. A few people are at the historic site, but they're walking their dogs around the grass, not gawking at the 221-foot obelisk. After a half loop around the monument, I walk down the hill through the centuries-old brownstones to Warren Tavern.

The doorman checks my ID and I find a seat at the bar. The place has low ceilings and plenty of TVs broadcasting sports channels. Warren Tavern is by far the most family-friendly spot I've visited so far. Tables are peppered with young children drinking from kid's cups. The bartender seems to know the name of everyone who walks in.

The menu tells the Warren Tavern story, about how Dr. Joseph Warren opened it in 1780. George Washington came around these parts, and now I'm eating $16 fish and chips on the same hallowed ground.

Tommy is from Southie—that's South Boston, not South End, Boston—and works at MIT. After work, he comes to Warren Tavern for a Budweiser and reads the newspaper alongside his friends. He shows me photos on his iPhone of last winter's snowmageddon.

"There are too many young professionals at the bars near work," Tommy says. "This is a neighborhood spot."

Across the room, a table full of ladies are exchanging gifts and laughing loudly. Tommy asks me if I've bought my Powerball ticket yet and we joke about the odds. Someone yells out, "Roll tide, baby!" and a conversation breaks out about Alabama football.

There is something deeply comforting about taking a seat at their worn, wooden bars and not dealing with 14-page cocktail lists. Sure, they are also probably deeply uncool, but if they were good enough for Paul Revere, they're good enough for me.