Boston is the oldest major city in the United States and makes no effort to conceal it. The street plan — a chaotic network that follows the logic of colonial-era cow paths rather than any subsequent grid — resists navigation, the accent resists imitation, and the civic pride resists modesty. It is a compact city by American standards, genuinely walkable, and dense with history in a way that most American cities simply are not. Almost every street in the centre has something that happened on it.
We’ve been to Boston twice. The first time was a whirlwind bus tour that stopped in most of the big East Coast cities just about long enough to catch your breath. I remember the harbour, and eating seafood in a fancy restaurant by the waterside. On the second visit, we flew into Logan airport and stayed a couple of nights downtown before renting a car to drive across country to California. I was surprised by the small size of Logan airport. It didn’t seem like a tourist destination. Yet, it’s New England and 20 million tourists do make their way to Boston each year attracted by the history, the sports, the academia, and perhaps the food culture. We saw just a fraction of what Boston and its surrounds had to offer. We’d go back there without question.
A Little Background
Boston was founded in 1630 by Puritan colonists from the Massachusetts Bay Company, on a small peninsula in Massachusetts Bay. It became the largest and most significant city in British colonial America and, accordingly, the site of most of the events that led to the American Revolution. The Boston Massacre (1770), the Boston Tea Party (1773), the battles of Lexington and Concord and Bunker Hill (1775) — the revolution was, in large part, a Boston production. Paul Revere, Samuel Adams, and John Adams were all Bostonians.
The nineteenth century brought the Irish, who fled the famine in enormous numbers after 1845 and transformed the city’s character permanently — Boston’s political and cultural identity is still shaped by that immigration in ways that are immediately visible. Harvard (founded 1636) and MIT (founded 1861) sit across the Charles River in Cambridge, and the concentration of universities — there are over 100 in the greater Boston area — gives the city a perpetual intellectual energy and a younger population than its historical weight might suggest.
What to See and Do
The Freedom Trail is a 4-kilometre walking route marked by a red line (painted or brick) through central Boston that connects sixteen historically significant sites — from Boston Common to the Bunker Hill Monument in Charlestown. You can follow it independently (free; the National Park Service provides maps) or join a guided tour (approximately US$15–20 per adult). The highlights include the Paul Revere House (Boston’s oldest remaining structure, built around 1680), the Old North Church (from whose steeple the famous “one if by land, two if by sea” lanterns were hung), and the USS Constitution — “Old Ironsides” — the oldest commissioned warship still afloat, berthed at the Charlestown Navy Yard. Allow three to four hours; more if you stop at the sites rather than passing them.
Fenway Park has been the home of the Boston Red Sox since 1912 and is the oldest Major League Baseball stadium still in use. Even if you have no particular interest in baseball, attending a game at Fenway is worth doing for the atmosphere, the crowd, and the architecture. The “Green Monster” — the 11-metre-high left field wall, built to stop balls leaving the park and now one of the most famous features in American sport — must be seen in person to be properly understood. Tickets for most regular-season games can be found for US$30–80; popular matchups cost considerably more.
The Museum of Fine Arts on Huntington Avenue holds one of the strongest art collections in the United States — particularly its ancient Egyptian collection, its American paintings, and its Asian art. Adult admission is approximately US$27. The Isabella Stewart Gardner Museum, ten minutes’ walk away, is smaller and stranger: a Venetian-style palazzo filled with the idiosyncratic collection of its founder, displayed according to her explicit instructions and therefore unchanged since her death in 1924. It is one of the more unusual museum experiences in the country.
Harvard Square in Cambridge (across the Charles River, a short Red Line subway ride from downtown) rewards an hour or two of wandering — the university buildings, the Coop bookshop, the density of cafés and independent shops, and the general atmosphere of a university town that takes itself seriously. The Harvard Art Museums (adult approximately US$20) house a genuinely excellent collection spread across three connected buildings.
Boston Common and the Public Garden form a continuous green space in the centre of the city — Common (the oldest public park in the United States, established 1634) is functional and open; the Public Garden is ornamental, with a lagoon, weeping willows, and the famous Swan Boats that have been operating since 1877. Free to enter.
The North End is Boston’s Italian neighbourhood — a dense, noisy, delicious enclave of red-sauce restaurants, pastry shops, and coffee bars around Hanover Street. Mike’s Pastry and Modern Pastry face each other across the street and have maintained a decades-long rivalry over the city’s best cannoli. The correct answer is that you should try both.
Quincy Market / Faneuil Hall is the tourist-facing version of central Boston — a market hall and food court in a restored 1826 building. The hall itself (Faneuil Hall proper) is a genuine historical site where revolutionary meetings were held; the market around it is now largely chain restaurants and souvenir shops, but the architecture is worth seeing.
Getting There
Boston Logan International Airport (BOS) is 5 kilometres from downtown, connected by the Silver Line bus (free from Logan to South Station) and the Blue Line subway (US$2.40 to downtown). The journey takes 20–30 minutes. Taxis from the airport cost approximately US$30–45.
Amtrak’s Acela and Northeast Regional services run frequently between Boston South Station and New York Penn Station (approximately 4 hours by Acela, 5 hours by Regional). Washington DC is approximately 7–8 hours by train. Boston is the northern terminus of the Northeast Corridor rail network, which is the most useful rail route in the United States.
Cost and Hours
Boston is expensive — roughly comparable to San Francisco. Mid-range hotels in the centre run US$200–350 per night; the university population keeps food costs slightly more varied, with good options across price points. The Freedom Trail, the Common, and the Public Garden are free. Allow three days minimum; four if you want to include Cambridge properly and a day trip to Plymouth, Salem, or Cape Cod.