Boston’s reputation as one of the country’s most traversable cities is based on an incongruous network of streets. Many shoot off at sudden angles. Some stop and resume blocks later with no apparent plan. Some are circular or banana shaped. Your standard Midwestern grid—or even your standard New York grid—generally doesn’t apply here. Boston’s streets were first built for horses and carriages and people on foot—not cars.
Perhaps that’s why pedestrians find these European-style byways among the most enjoyably walkable in the country. Perhaps it’s also why locals defend their driving rights as if they were still fighting the Revolution, and why newcomers are advised to turn onto those same streets only after an intensive course in defensive driving.
Consider the following observation by travel writer and humorist Bill Bryson after a drive on the Expressway (Route I-93). “Boston’s freeway system is insane. It was clearly designed by a person who had spent his childhood crashing toy trains.”
Also consider those freeways as a rough, protective shell to one of the U.S.’s last true connections to the Old World. And, then, head out on foot—it’s a more peaceable way to explore the roots of American history.
One of Boston’s most significant, and longest, streets was named in 1788 for America’s famous Revolutionary general and first President, because of his triumph during the Siege of Boston. The Continental Army had sealed off the thoroughfare because it was the only road that led into and out of what was, at the time, a peninsular city. This trapped the British troops and prevented them from getting supplies.
As Washington bombed the British out of town in March 1776, they scattered some nasty forget-me-nots. “They laid crows' feet in the road,” explains Robert Allison, a professor of history at Suffolk University. Jagged iron clusters were spread to tweak Washington and his men’s victorious march back into Boston.
Before being renamed to honor Washington, the street had actually been a link of four shorter streets: Cornhill was the northernmost section, starting at what is now the border of the North End and the Charlestown Bridge; Marlborough—a name that would later be transferred to a new street in the Back Bay—linked Cornhill with what is now Downtown Crossing; Newbury, which would also be later recycled, extended south to what is now the intersection of Boylston and Essex streets; from there, Orange Street extended out to present day South End and Roxbury, where General Washington maintained control of the city from a fort on the aptly titled, Fort Hill.
Back in the 18th century, short streets were vital. Historian J.L. Bell, who writes the Boston 1775 blog, says, “In the 1790s, they didn’t have street numbers, so it was important to keep streets short. If you had an address, you would say, ‘I live on Cornhill, near the blacksmith,’ or something like that. It wasn’t until they renamed it ‘Washington Street’ that numbering came in.”
Another unique feature of Washington Street: No street that intersects it continues on the other side with the same street name. Thus, Winter Street becomes Summer Street; Kneeland Street becomes Stuart Street, and Boylston Street becomes Essex Street. One thing, however, is impossible to determine: whether, or not, this Washington Street was the first Washington Street to be named for George Washington. Indeed, Boston alone features four others named "Washington."
Neighborhood: Downtown, Chinatown and South End
How to best explore: Carve out the better part of a day and walk it, from Downtown near its zenith at the Old State House to a good stopping point where it meets Massachusetts Avenue in the South End. Along the way, you'll encounter loads of department store shopping (Primark, H&M) and colonial sites (Old South Meeting House, to name one) in the Downtown Crossing area, historic playhouses (Opera House, Paramount Theater) as you move into the Theater District, vibrant culinary offerings from an array of Asian traditions in Chinatown, and finally, independent boutiques and sophisticated, chef-driven restaurants in the South End.
Although there is no center for education on this street any longer, School Street’s name couldn’t be more appropriate.
It’s the site of the country’s first public school, Boston Latin. In 1645, a wooden schoolhouse was constructed here in an attempt to offer public education to all residents. Poor families often had to pull their children out of school at an early age to work, so Boston Latin became known as a public school for Boston’s more privileged families.
Ironically, more than a few Boston Latin dropouts went on to become world-famous. Benjamin Franklin left as a teenager so he could work in his brother’s print shop. Henry Knox, a future patriot, also had to terminate his Latin education early. John Hancock and early rabble-rouser Samuel Adams (also the cousin of future president John Adams) were other alumni. Today, an ornate brass and ceramic mosaic embedded in the courtyard in front of Boston’s Old City Hall commemorates the legacy of the school that now operates in the Fenway neighborhood and remains the pride of the city’s educational system. Students are still required to take four years of Latin in order to graduate.
How to best explore: School street is very short—only about one city block. Take it in while you walk The Freedom Trail; it follows King's Chapel and Burying Ground, and precedes the Old Corner Book Store.
Mt. Vernon Street
Residential development of Beacon Hill began in earnest in the early 19th century, but the area we now know as Beacon Hill was originally three hills: Mount Pemberton, Beacon Hill and Mount Whoredom.
The name of the latter hill left nothing to the imagination and was the site of several brothels particularly favored by officers in the British army. “There was also a Mount Whoredom in London, where the Royal Artillery had its training ground," Bell said. "So that’s what the British officers liked to call it.”
For his part, Washington was decidedly embarrassed by it. “Washington called it Mount Horam—a biblical name—because he couldn’t bring himself to say the other name,” said Bell.
Atop our former lasciviously titled hill, Mt. Vernon Street cuts past the Massachusetts State House, continues through the upscale block known as Louisburg Square (Senator John Kerry lives here, and Louisa May Alcott used to) before heading downhill to Charles Street.
Mt. Vernon Street was given a name designed to appeal to prospective property buyers. In another nod to the general, it recalls his own Virginia estate. After all, Mount Whoredom may have been marketable for a certain demographic, but it wasn’t land buyers.
Neighborhood: Beacon Hill
How to best explore: In season, both Historic New England (through its Beacon Hill Walking Tours) and Boston By Foot, host informative and fun guided adventures through this most posh neighborhood, in season, which is usually May through October. Otherwise, check it out between visits to Boston's Museum of African American History and shopping or lunch along Charles Street.
State, Court and Federal Streets
Immediately following the American Revolution, Boston’s 18th-century inhabitants did not want to be reminded of British rule. Accordingly, they changed many of the street names that had been imported from the old country—much like the name of our region, New England.
King Street turned to State Street. Queen Street turned to Court Street. Long Lane, named after a famous road in London, was renamed Federal Street.
Another of the names to go was Hutchinson Street, because of its connection to one of the most reviled politicians in Colonial history. Governor Thomas Hutchinson was a hard-line opponent of the Sons of Liberty, the activist group of which members included Samuel Adams, Paul Revere and John Hancock. Hutchinson attempted to enforce the Tea Act, the tax legislation that ultimately triggered the Boston Tea Party, and two of his sons were merchants who held consignments for the shipment of tea that was dumped into Boston Harbor. Today, it’s called Pearl Street.
Curiously, a street with a direct connection to British royalty remains to this day. Hanover Street in the North End was named for King George I, who came from the House of Hanover.
Neighborhood: Downtown and Financial District
How to best explore: Old State House and the site of the Boston Massacre is the star attraction on State Street. Incidentally, much of State Street as it exists now used to part of Long Wharf. Follow it right to the water for dinner at the Chart House, John Hancock's former counting house. Federal Street runs out of Post Office Square in Boston's skyscraper zone, so there's not much for travelers to see and do here.
Newbury Street, plus Arlington through Hereford Streets
Before the Back Bay became a neighborhood of expensive Victorian-era homes and chic shopping, it was submerged under the waters of Boston Harbor.
During the Revolution, General Washington, who was originally encamped in Cambridge, crossed it when he first invaded to reclaim Boston.
By the mid-19th century, the city had a demand for space, so more than 1,000 acres of the salt marsh area was converted into solid ground.
The landfill project started in 1857 near Boston Common and over the next 25 years an urban grid of parks and wide boulevards emerged. Combined with the elaborate development of nearby Copley Square, the Back Bay greatly enhanced Boston’s continental—many would even call it “British”—nature, despite having sent the Brits packing less than 100 years earlier.
When it came time to name the newly formed streets, Bostonians looked back across the pond for inspiration. The two-mile stretch that has become Boston’s most fashionable avenue was named Newbury Street, recycled from one that had been scrapped with the retitling of Washington Street. Likewise, Marlborough Street, parallel to Newbury, was reborn.
The Back Bay’s alphabetically arranged cross streets, perpendicular to Newbury and Marlborough, bear the monikers of English earldoms: Arlington, Berkeley, Clarendon, Dartmouth, Exeter, Gloucester and Hereford.
The one exception is Fairfield Street. Though there is no record of snob appeal being an official real estate plan, it’s clear that city planners longed to retain their royal connection. “A lot of the Brahmans were Anglophiles,” explains Allison. “They saw themselves as part of the upper class world.” Fittingly, the Back Bay became the most popular neighborhood in the city, considered, at the time, more exclusive than Beacon Hill.
Neighborhood: Back Bay
How to best explore: Leisurely stroll up Marlborough Street and then back through the Commonwealth Avenue Mall (green space, not shopping), which runs parallel. You'll have worked up an appetite, so stop for lunch at one of the cafes on Newbury Street and then shop this posh place's independent fashion stores, European designers and more.