For Children -- The timeless classic Make Way for Ducklings, by Robert McCloskey, tells the story of Mrs. Mallard and her babies on the loose in the Back Bay. After your kids fall for this book (and they will), you can thrill them with a trip to the Public Garden, home to bronze statues representing the family.
Slightly older kids might know the Public Garden as the setting of part of The Trumpet of the Swan, by E. B. White. After reading it, a turn around the lagoon on a Swan Boat is mandatory.
An excellent historical title is Johnny Tremain, by Esther Forbes, a fictional boy's-eye-view account of the Revolutionary War era. The book vividly describes scenes from the Revolution, many of which take place along the Freedom Trail.
We're Off to Harvard Square, by Sage Stossel, is a delight, written in sprightly verse and beautifully illustrated. It's intended for 9- to 12-year-olds, but younger kids and adults will like it, too.
For Adults: An excellent introduction to the city's early history is Paul Revere and the World He Lived In, Esther Forbes's look at Boston before, during, and after the Revolution. Common Ground: A Turbulent Decade in the Lives of Three American Families, by J. Anthony Lukas, is the definitive account of the busing crisis of the 1970s and the attendant social upheaval. Both won the Pulitzer Prize for nonfiction. In the fiction section, Edwin O'Connor captured Boston machine politics in a book many have challenged but none has surpassed, The Last Hurrah.
The Proper Bostonians, an entertaining, perceptive nonfiction look at a bygone era that helped earn Boston its longstanding reputation for stuffiness, is an early work by well-known animal-rights activist Cleveland Amory. The Friends of Eddie Coyle, by George V. Higgins, is a crime novel famed for its realistic dialogue and unvarnished take on Boston hoods. Black Mass, by Dick Lehr and Gerard O'Neill, updates the story of local organized crime with a nonfiction take on the rise of mobster James "Whitey" Bulger. The novels of Dennis Lehane are required reading for Boston-bound fans of mysteries and crime fiction.
Architecture buffs will enjoy Cityscapes of Boston, by Robert Campbell and Peter Vanderwarker, and Lost Boston, by Jane Holtz Kay. If trivia's your thing, check out the treasury of "did you know" items in Boston A to Z, by historian Thomas H. O'Connor.
"Paul Revere's Ride," Henry Wadsworth Longfellow's classic but historically outlandish poem about the events of April 18 and 19, 1775, is collected in many anthologies. It's a must if you plan to walk the Freedom Trail or visit Lexington and Concord.
If you're venturing to Gloucester (or even if you're not), Sebastian Junger's The Perfect Storm makes a good introduction. The story of a fishing boat caught in historically bad weather will change the way you look at fish on a menu for a long time after you finish reading or watching. The movie version, though heavy on the special effects, is a better-than-average effort.
The cast of Good Will Hunting (mostly) pulls it off. Stars Ben Affleck and Matt Damon grew up in Cambridge and wrote the Academy Award-winning screenplay together. This is the Boston movie to see if you have time for just one.
The Departed (2006), The Perfect Storm (2000), and Mystic River (2003)—the latter, like Shutter Island and Gone Baby Gone, based on a novel by Dennis Lehane—are among the best 21st-century movies with Boston-area backdrops. Other pictures worth checking out for more than just the cheap thrill of recognizing the locations include A Civil Action, The Spanish Prisoner, Next Stop Wonderland (all Boston), State and Main (Manchester-by-the-Sea), and The Love Letter (Rockport).
If you have a high tolerance for sports and sentiment, check out Fever Pitch, a 103-minute video valentine to Boston and the Red Sox. Many scenes were filmed at Fenway Park, and the ending had to be reshot after the Sox won the World Series in 2004 for the first time in 86 years. The script is sappy but captures the maniacal-fan persona with alarming accuracy, and the soundtrack is terrific.
Consider streaming these older movies, too: Blown Away (especially the scenes when the action first shifts to Boston), The Verdict and The Friends of Eddie Coyle (Boston), Glory (a stylish re-creation of 19th-c. Beacon Hill), The Witches of Eastwick (Cohasset), and the sentimental favorite, Love Story (Cambridge).
Most TV shows set in Boston use an occasional exterior location shot but otherwise don't get anywhere near the city. They include Rizzoli & Isles, Boston Legal, The Practice, St. Elsewhere, and Spenser: For Hire (if you can find it). But that's not why you're wondering whether everybody knows your name, is it? Cheers was based on a local pub called the Bull & Finch, and the show became so popular that the original bar changed its name and a spin-off opened in Faneuil Hall Marketplace.
Highbrow associations abound: The first American performance of Handel's Messiah was in Boston, the city is home to one of the best orchestras in the world, and the Boston Symphony even commissioned a recent Pulitzer Prize winner (George Walker's "Lilacs"). The 1970s and '80s were the heyday of local rock, with Boston (the band), the Cars, and the J. Geils Band leading the pack. But the piece of music perhaps most closely associated with the city is the Standells' "Dirty Water." Released in 1966, it was written by the band's producer after he was mugged on the Massachusetts Avenue bridge, which connects Boston and Cambridge "down by the banks of the river Charles."
The movie soundtrack to seek out is Fever Pitch, a superb collection of songs associated with Boston. It includes "Dirty Water" and Neil Diamond's "Sweet Caroline," a random selection that caught on out of superstition and now booms through Fenway Park in the bottom of the eighth inning of every Red Sox home game.
Download the Dropkick Murphys' "Tessie" and Augustana's "Boston," dig through your grandparents' LPs to find the Kingston Trio's "Charlie on the MTA," learn the words to "Where Everybody Knows Your name" (the Cheers theme song), and you'll be well on your way to passing for a local.
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