Boston has produced more than its share of American writing. Henry James, Henry Adams, William Dean Howells, Robert Lowell, and Sylvia Plath all wrote about the city's particular weight of class, history, and self-regard. More recently, Dennis Lehane has done for working-class Dorchester and South Boston what Hammett did for San Francisco — given it a sharp, durable literary voice. The novels below are the ones to read before you arrive.
Make Way for Ducklings — Robert McCloskey's 1941 picture book about a family of mallards making their way from the Charles River to a permanent home on the lagoon in the Public Garden is the children's book that every Boston-born child grows up with. Mrs. Mallard waddles across Beacon Hill with eight ducklings — Jack, Kack, Lack, Mack, Nack, Ouack, Pack, and Quack — stopping traffic on Beacon Street until a friendly policeman helps them across.
The bronze sculpture of Mrs. Mallard and her brood in the Public Garden, dedicated in 1987, draws steady streams of small children, who climb on the ducklings and rub their bills shiny. A duplicate set sits in Moscow's Novodevichy Park, a 1991 gift from Barbara Bush to Raisa Gorbacheva.
Mystic River — Lehane's 2001 novel is set in a fictionalized version of East Buckingham, modeled on the Irish working-class neighborhoods of Dorchester and Southie where Lehane grew up. Three boys are playing in the street when one of them is pulled into a car by men pretending to be police; the rest of the book is the long shadow of that single afternoon. Twenty-five years later one of the men is a hard-luck ex-con, one is a tightly-wound store owner whose daughter has just been found dead, and one is the homicide detective working the case.
It is a crime novel, but really a novel about the working-class Boston the tourists never see — bars under elevated tracks, three-deckers, parishes, grudges that last generations. Eastwood made a faithful film of it in 2003. The book is better.
The Friends of Eddie Coyle — George V. Higgins, a former federal prosecutor, wrote his 1970 debut in the kind of plain, profane, tape-recorder-accurate dialogue that no one had really put on the page before — every conversation in a Boston bar, every double-cross arranged over the phone, every plea bargain laid out by a tired AUSA. Eddie Coyle is an aging Boston gunrunner two-stepping between the FBI and the people he is informing on; the book is the slow tightening of a noose neither side wants to admit they are pulling.
Elmore Leonard called it the best crime novel ever written. The Robert Mitchum film of 1973 is a perfect adaptation. Read the book first.
The Given Day — Lehane's most ambitious novel covers a single year — 1919 — in Boston, when the city was hit by the Spanish flu, a molasses flood, a race riot, and the famous police strike that ended the careers of the entire force. Two parallel lives run through the book: Danny Coughlin, an Irish cop wrestling with whether to join the strike, and Luther Laurence, a Black domestic worker fleeing trouble in Tulsa who finds his own kind of trouble in Boston.
Babe Ruth appears throughout in extended interludes, in his last year with the Red Sox before the sale to the Yankees. It is a sweeping historical novel of a city that was visibly remaking itself, and Lehane gets the period right without ever lapsing into pastiche.
The Late George Apley — Marquand's 1937 Pulitzer winner is the fictional posthumous biography of a Beacon Hill patriarch, told through letters, diary entries, and tactful editorial gloss. Apley is a Harvard man of solid Brahmin family who never quite breaks free of the conventions that surround him: the right club, the right wife, the right summer house, the right opinions. The satire is gentle and the affection is real — Marquand was himself the kind of mannered insider he was writing about.
It is the funniest portrait of upper-class Boston ever written and an indispensable counterweight to the Irish Boston of Lehane and Higgins. The novel is also a useful map of where the old money lived and how.