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Source: Dear travelers, please don’t visit Boston until you’ve understood these 10 things
1. Don’t let The Town fool you into thinking Charlestown is some organized-crime-ridden place.
Charlestown, portrayed in the Ben Affleck film as some sort of townie hub for bank robberies, is really quite a nice place. A walk around the winding, thin colonial streets today will show you nothing more than a square mile-long working class suburb that’s slowly being gentrified by Boston yuppies (Young Urban Professionals).
Sure, Charlestown has flirted with organized crime like the Irish gang war in the 60s between the Charlestown Mob and the Winter Hill Gang in Somerville. And the townies there definitely didn’t come across as the forgiving type during the “busing” conflict in the 70s. But this town is, if anything, fiercely proud of their heritage, tradition and role as one of America’s oldest cities. After all, Paul Revere galloped at high speed from here to the battle at Lexington and Concord to warn that “the British are coming!” John Harvard himself lived in Charlestown, Samuel F.B. Morse was a born and bred townie and the Charlestown Navy Yard is home to Old Ironsides, the oldest commissioned vessel in the US Navy.
2. But yes, Whitey Bulger is our resident gangster.
Bulger’s story might be a bit more common knowledge now to people outside the state of Massachusetts due to Johnny Depp’s portrayal of him in Black Mass. The notorious Boston crime boss of the Winter Hill Gang is both feared and iconized after terrorizing South Boston in the 70s and 80s, then disappearing in an attempt to escape an FBI indictment. In 2011, he was finally found in Santa Monica, California, strapped with an arsenal and over $800,000 hidden in the walls.
If you spend a lot of time in Boston, talk of Whitey isn’t uncommon, and neither are very distant relations to him. One friend of mine swears her dad worked in one of Whitey’s bars, another says his dad lived on Whitey’s block in Southie. Hell, I even met Kevin Weeks, Whitey’s right-hand man and leading rat in the case against Bulger and FBI agent John Connolly. One of my BU journalism professors, Phyllis Karas, wrote his memoirs with him and brought him into class to talk to us about the trial that was being held in 2013. Whitey was found guilty on 31 counts, including racketeering charges. He was found to have been involved in 11 murders, and later that year he was sentenced to two consecutive life terms plus five years.
South Boston is still a rougher part of Boston with embedded Irish working class residents still kicking about. However, the location and proximity to Boston’s downtown cannot be beat. Old triple deckers are making way for shiny new duplexes and not-bad pubs likeLincoln’s. I probably wouldn’t hang about some areas too late, though. Andrew Square, for example, still has the ghosts of brutality about it.
3. The Tea Party is much more than an uber-conservative activist movement.
Nowadays, when people hear the words “Tea Party” they think of painfully backward Republicans like Michele Bachman who see lowering taxes and limiting social freedoms as a pathway to getting our nation out of debt. But let’s not forget the Boston-based revolutionaries who once gave a ‘tea party’ a whole new meaning.
The Boston Tea Party was originally a badass political protest against the Tea Act of May 10, 1773 in which the Sons of Liberty dumped an entire shipment of tea sent by the East India Company into the Boston Harbor. It all went down on December 16, 1773 and was one of the straws that broke the Patriotic camel’s back and started the American Revolution. You can walk around the Harbor and sail along the Harbor Islands today, watching for whales and envisioning what truly revolutionary shit went down among that gray-blue salty water.
4. Beware the ‘Methadone Mile.’
It is easy to notice what drug addiction has done to many residents in Boston as you walk along the one-mile stretch of Massachussetts Ave near Boston Medical Center, otherwise known as ‘Methadone Mile’. Just a few blocks away from the clean brownstones and trendy cafes of Boston’s South End is a strip of methadone clinics, homeless shelters and drug treatment centers that have surfaced to try to combat Boston’s massive opioid addiction problem.
Residents walking their dogs would know to steer clear of this street for fear of their pet stepping on a used needle or picking up an empty heroin bag. I’m not exaggerating. The debris of addiction and the presence of junkies isn’t limited to the ‘Methadone Mile’– you can see the effects of the drug from Dorchester T stations to the lovely Fens gardens to Revere Beach. But in this location, however, it’s not uncommon to find addicts openly cooking and injecting drugs like it ain’t no thang. And to them, it isn’t, which should put it into the tourist’s head to be wary of people suffering and how that might affect their time in Boston.
5. We will always be proud of our role in the American Revolution.
Boston is rife with revolutionary history due to its role as a commercial center and home to some of the radicals we remember today like Samuel Adams (after whose namesake the Boston Lager was brewed) and John Adams. Just looking at a map of Boston and Massachusetts will make names of people and places from your history books jump out at you, from Revere and Quincy to Lexington and Concord.
If you feel like following in the footsteps of the Revolution that gave our nation the now-ridiculous reputation of ‘The Land of the Free,’ you can follow theFreedom Trail, which starts at the Boston Common park and goes to the USS Constitution.
6. We’re not an ignorant city; in fact, some of the world’s top universities are here.
It seems as though ‘America’s College Town’ always has been and always will be home to great minds and progressive thinking, and that idea only seems to be enhanced by the sheer amount of universities present. There are more than 100 colleges and universities in the greater Boston, Massachusetts area, most notably Harvard, MIT and Tufts.
In fact, this concentration of higher education in Boston has led to a steady increase in the population, leaving the city sort of grasping for housing. The Boston Redevelopment Authority found in a 2010 study that there are 152,000 students in Boston’s institutions, a number that had gone up about 20 percent since 1990 and, we can only assume, has gone up since.
7. Don’t visit during winter.
Many people who don’t get to really experience snow (I’m looking at you, Australia) love the idea of traveling around the States in the winter. A White Christmas! What a novelty! I urge you, however, to do yourself a favor and not come to Boston for its winter. Hell, New York, for all its sludge, is a better bet if you’re dying to freeze your ass off in a major US city. Boston is simply too miserable to show you a good time.
When winter comes to Boston, it settles in, and so do its residents. You will be welcomed not only by arctic winds, thigh-high snow and terrifying icicles hanging off the roofs, but also by bitter humans who are struggling from an ungodly combination of bone-chill, the flu, seasonal affectiveness disorder and daunting daily transportation issues. That painful moment when you wake up to a white-washed window only to realize that you must now dig your car out or else suffer the lagging and creaking MBTA is enough to make anybody’s day a miserable one. In addition, you’ll find yourself exhausted from putting on at least three extra layers of clothes only to take off two of them in a huff the second you walk into any heat-pumped building. Heading to the pub later? Count almost everyone in Boston out. They’d rather drink inside and watch the Pats game.
8. Nightlife ends early here.
Prepare yourself to start and end your night much earlier in Boston than you would in many other major cities. Most bars are only open until 2 am, so if you think that’s the time when the party is kicking off, you will be sadly mistaken and left with booze blue balls. Don’t even try to get another one off the bartender at 2:01. It’s not gonna happen.
9. You should bring your passport to the pub.
If you are planning on one of these early nights out, make sure to bring a proper form of ID and expect to get carded almost everywhere. Boston is notoriously strict about ID-ing as it is a college town and there are plenty of underage kids just trying to have a drink in a social setting like a normal adult. Foreigners will often find themselves turned away by many bartenders for not having their passport on them. No, we don’t accept your country’s driver’s license. Military ID cards are usually considered OK.
10. Seafood is good here, eat all that you can afford.
New England seafood is well known for being some of the best in the world, so don’t leave without getting your hands on some. From the hearty Boston Clam Chowdah to a succulent and fresh Lobster Roll, you’ll be writing back home to Mom about it.
If you’re looking for a bit of history, check out Union Oyster House, America’s oldest remaining restaurant. It was built in 1826, it looks like a ship inside, and it’s alright. You can do better when it comes to New England seafood in Boston. I’m a casual seafood eater myself, so a walk through Quincy Market to Boston & Maine Co. for some steamed mussels will never go amiss. Also a big fan of Faneuil Hall’s Salty Dog for the sheer joy of watching the bartender shuck those fat Martha’s Vineyard oysters right in front of me. The Barking Crab is also a local favorite, as I love a chance to sit in a big red-and-white tent on Fort Point Channel in the Seaport District while I smash salty Fried Clams and buckets of King Crab. 
