On the Trail of Movie ‘The Departed’ in Boston USA

You arrived at one of the many hotels in Boston, probably after a long plane journey and a fleeting cab or bus ride through the enormity of the metropolis; so now what? A city like Boston – as sprawling in size as it is indomitable in spirit – can be a little overwhelming to the uninitiated. There can be few better ways to delve into the heart of a city than to follow the trail of a modern cinematic classic, and they don’t come much more cinematic than Martin Scorsese’s 2006 gangster epic, The Departed.

Sure it’s directed by one of New York’s most famous auteurs, and features Hollywood’s own Leonardo DiCaprio in its starring role, but The Departed is as complete a love letter to Boston as you can imagine. This is no blinkered paean, no rose-tinted jaunt through a city that can barely be said to exist; The Boston of The Departed is presented in a scathing, warts-and-all light which truly captures the ethos of this fascinating place, all the while remaining as stirring to the blood of a Bostonian as any rendition of ‘Tessie’ from the Fenway faithful.

Chinatown and Suffolk University

Our journey begins in Chinatown, the setting of the thrilling incognito chase between Matt Damon’s Colin Sullivan character and Leonardo DiCaprio’s Billy Costigan. This scene – key to the development of the awkward relationship between Sullivan and Costigan – was filmed in the maze of streets behind the Washington Street Theatre District on Chinatown’s west border.

Boston’s Chinatown ranks amongst the oldest districts of its type anywhere in the U.S., and the oldest surviving Chinatown settlement in New England. It’s an ideal place to find some of the most reasonably priced and centrally located hotels in Boston, and also boasts a wealth of excellent restaurants and entertainment venues in the nearby Theatre District.

From here we head westwards, crossing Washington Street and continuing for a few blocks onto Tremont Street, bordering the semi-legendary Boston Common. One of Boston’s most famous locations – and surely its most internationally renowned green space – the Common has been an integral part of Boston’s history since the 17th century. You’ll have time to take it all in later, for now we head north, up Tremont Street and past the Common’s north-eastern tip.

As you reach the Granary Burying Grounds – the final resting place of such celebrated Bostonians as Samuel Adams and John Hancock – you will see the Suffolk University School of Law on your right. This building was the location for some of The Departed’s cornerstone scenes, including its heart-stoppingly shocking ending.

Boston Common

Of course we couldn’t stay away from Boston Common for too long. Artists and writers – from Sylvia Plath to Craig Finn – have been referring to the Common in their work for generations, so it’s only right that such a culturally significant space should be featured in The Departed. Entering the Common at Park Street Station, we traverse the thin end of the park’s wedge shape, heading north to Beacon Street. It is here, at number 84, that the disturbing character of Jack Nicholson’s Frank Costello is laid bare before the audience as he demands protection money from a local bookkeeper.

Loosely based on infamous Boston mobster, James “Whitey” Bulger, Nicholson’s Costello is as unsettling as he is fascinating. The veteran actor delivered one of his trademark maverick performances for the role, ad-libbing much of his dialogue and throwing in a number of his own stylistic touches that disturb and enthrall audiences in equal measure. Surely one of the greats of his generation, if not of all time, Nicholson does not disappoint.

You might want to take a little longer to explore what Boston Common and the surrounding district has to offer. Reasonably priced hotels in this area can be found on Hipmunk.com – a travel search engine recommended by PCMag, amongst others – and Boston Common makes for a great base camp for any trip to Boston.

Shipping out to Quincy

From here we have about a half-mile walk to Long Wharf, a Boston ferry-port where the dramatic confrontation between Frank Costello and Mark Wahlberg’s Detective Sergeant Dignam was filmed. Riding the ferry south from Long Wharf to Quincy is a great way to take in the majestic skyline of Boston, and appreciate the maritime history of the city. It also handily connects us with our next, literal, port of call; Quincy, Massachusetts’ own Fore River Shipyard.

Chances are if you’re reading this article, you’ve seen The Departed at least once. But just in case you haven’t, we won’t spoil it for you. Suffice to say, the historic shipyard is the scene of some major fireworks when Sullivan catches up with Costello’s crew late on in the movie. This is a Scorsese movie, so you know that what transpires is smart, bloody and pleasingly foul-mouthed.

Quincy may be predominately an industrial town but it’s in possession of some pretty impressive history that rivals even that of its more famous neighbor, Boston. Two presidents were born here, as well as renowned signatory to the Declaration of Independence, John Hancock, not to mention the countless warships – including the USS Lexington  – that began their lives in the city’s dockyards. Quincy also gave the U.S. its first commercial railroad.

Any visit to Boston is incomplete without some time spent south of the Neponset River. There are plenty of hotels in Quincy, with prices to suit a range of budgets.

Back to Boston

Riding back north into Boston on the Red Line brings us to Boston’s South Station, a leviathan of a transport hub which is the second largest in New England after Logan International Airport. This is the location of Costigan’s first meeting with Martin Sheen’s Detective Queenan, laying down another layer of deceit and intrigue on an already slippery plot.

It’s here that our cinematic Boston odyssey comes to an end. The Departed is a scintillating adventure; frequently brutal and downright scary in places, but don’t let that put you off a trip to this jewel of New England. You don’t just visit Boston; you embrace it.

Know of any spots we’ve missed on our trail of Scorsese’s classic movie? Let us know in the comments!

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