OPS Boston streets Pi Alley Photo by Joseph Runci, Boston Globe Nov 26, 67 / bw
Pi Alley might be the oldest byway in Boston, but don’t ask any of the thousands who use the 8-foot-wide walk-through where its name comes from.
Joseph Runci/Globe Staff/File 1967

One of the city’s oldest byways, frozen in time

Brian Schweizer has worked in Pi Alley for 12 years, but how the downtown shortcut got its name is a mystery to him.

“I have no idea,” Schweizer said at Archie's Place, a small restaurant tucked off the walkway’s uneven red bricks.

“I don’t, either,” said Solomon Ketema, a Pi Alley Garage employee who wears a polo shirt with the alley’s name stitched on the front.

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Don’t feel bad, guys. Alleys are mysterious by nature, this one more than most.

Considered one of the oldest byways in Boston, Pi Alley has a long, murky past that leaves the true origin of its name open to interpretation and guesswork.

“I used to think this was a place where they baked pies,” said Walter Williams, who commutes from Norwell.

People made their way through Pi Alley.
People made their way through Pi Alley.
Lane Turner/Globe Staff

“I would just assume it’s the 3.14 math number,” offered Charles Blizard, 24, of Dover.

For a city that prides itself on its past, the etymology of Pi Alley — a narrow pedestrian bee-line that runs from Washington Street to Old City Hall — is a head-scratching helping of obscure urban legend. Even the proper spelling has long been in dispute.

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“Is it Pi Alley or Pie Alley?” The Boston Globe asked in 1920.

Nearly a century later, the answer remains elusive. What’s not disputed is the historical importance of a street at the heart of Boston’s development through the centuries, as well as part of the most direct route from Beacon Hill to Long Wharf.

As one of the oldest streets in Boston, the alley has witnesssed centuries of history, including in August 1920 (left) when crowds linded the street hoping to collect on their 90-day notes at the nearby office of one Charles Ponzi. People made their way through Pi Alley (right).
As one of the oldest streets in Boston, the alley has witnesssed centuries of history, including in August 1920 (left) when crowds linded the street hoping to collect on their 90-day notes at the nearby office of one Charles Ponzi. People made their way through Pi Alley (right).
Globe file (left) and Lane Turner/Globe Staff

John Winthrop, a founder of the Massachusetts Bay Colony, lived nearby. Boston’s first beer-pouring inn opened here in 1634. Charles Ponzi worked his pyramid scheme in the area. A movie theater and myriad bars have come and gone. And rambunctious Newspaper Row, a fixture until the mid-20th century, kept the neighborhood buzzing.

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It’s that legacy — competing newspapers set cheek by jowl along a claustrophobic stretch of Washington Street — that points to what many Bostonians consider the most likely explanation for Pi Alley.

“Pi,” a spelling used by Benjamin Franklin as a young printer, refers to jumbled bits of small, lead type upended or scattered during the painstaking process of setting the letters for printing.

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Instead of sorting through the mess, piece by time-consuming piece, the “pi” sometimes was shoved in a typesetter’s pocket or tossed out the composing-room window. For many years, the legend goes, showers of pi rained on the alley below.

The Boston Herald once occupied a building on the alley, as did the Boston Post. And the Globe covered the news from across the street. There was never a shortage of pi, and never a shortage of typesetters, pressmen, reporters, and editors jostling down the alley to hoist a beer at the Bell in Hand, which once was located here.

Boston , MA - 07/10/18 - Pedestrians pass the entrance to Pi Alley on City Hall Avenue. Pi Alley might be the oldest byway in Boston, but don't ask any of the thousands of people who use the 8-foot-wide walk-through where its name comes from. Is it 'pi,' the magical mathematical number? Short for 'pie,' as in dessert? Or 'pi,' the bits of lead type that spilled from the overstuffed pockets of typesetters who shuttled between the composing rooms along old Newspaper Row and the alley's bars? The answer might never be known. (Lane Turner/Globe Staff) Reporter: (Brian MacQuarrie ) Topic: (12piialley)
Pedestrians passed the entrance to Pi Alley on City Hall Avenue.
Lane Turner/Globe Staff

If pi wasn’t falling from windows, it almost certainly was spilling from the pockets of typesetters groping for change to buy another round.

That’s the story that Kale Rogers has heard, and he’s done plenty of research. The 24-year-old owner of Spyce, a popular new restaurant on the alley where robots do the cooking, said he became fascinated by the site and dug into its past.

“It was a personal mission to understand what the area is about,” said Rogers, who was raised in small-town Oregon. “This area is super-cool for history.”

Peter Drummey, librarian of the Massachusetts Historical Society, added that the name game is super-complicated. Pi Alley’s murky nomenclature has confounded Bostonians for generations.

“I suspect there is no ‘right’ answer,” Drummey said. “And it goes along with my general suspicion that sometimes the logical answer to a historical question may not be the correct answer.”

Bicycles were parked recently in the alley, the name of which may be tied to the cith’s newspaper past.
Bicycles were parked recently in the alley, the name of which may be tied to the cith’s newspaper past.
Lane Turner/Globe Staff

According to Drummey, the Boston Street Laying-Out Department recorded the byway in 1910 as Pie Alley, which it called “a colloquial name by reason of the number of restaurants formerly in the alley.”

The passage had previously been listed as Williams Court, a name the city traced back to 1788 or 1789. The department “then unhelpfully notes that the name ‘Williams’ was accepted by the city in 1862 and then ‘rescinded’ in 1864, although it continued to appear in lists of Boston street names,” Drummey said.

Today, the official designation is “Pi,” which Drummey, ultimately, finds more probable than the edible explanation.

“It seems hard for me to believe, given that the section of Washington Street . . . onto which Pi Alley opens was long at the heart of the publishing and newspaper district of Boston, that this name is not from the printers’ definition,” Drummey said.

That’s the conclusion now held by Williams, the Norwell commuter who thought the alley was named for pies until his grandfather, Walter Francis, set him straight.

Francis, who died three years ago at age 101, had been an engraver at the Globe and Herald who knew his history first-hand, Williams said.

It’s pi, not pie, Francis told him. And it’s definitely not 3.14.

“He told me he used to throw them out,” Williams said of the jumbled type. “They’d toss them out the window.”

Now, perhaps, the debate can be tossed out the window as well.