New Book Looks at City’s 50 Oldest Buildings, Including One on Pinckney Street

A new book that looks at the 50 oldest buildings in the city includes only one on Beacon Hill, which admittedly came as somewhat of a surprise to the author.

“I figured there would have been a least a couple of them, but Beacon Hill as a neighborhood kind of appeared out of nowhere around 1800,” said Joseph M. Bagley, the city’s archeologist and author of “Boston’s Oldest Buildings and Where to Find Them” (2021 Brandeis University Press). “The reality is if I had made it ‘Boston’s 100 Oldest Buildings and Where to Find Them,’ at least half of them would be in Beacon Hill or in Charlestown.”

Coming in at #34 on Bagley’s list of 50 is Beacon Hill’s sole entry – the Glapion-Middleton House at 5 Pinckney St. (circa 1786).

In 1786 – just two years after Massachusetts abolished slavery – two Black men purchased an undeveloped lot at the corner of Pinckney and Joy streets, and they built the house at 5 Pinckney St. between 1786 and 1787.

Col. George Middleton was a free Black man who fought in the Revolutionary War as the leader of the all-Black rebel militia company, as well as a horse tender by profession, wrote Bagley, while Glapion was an abolitionist, who, in 1796, helped organize the Boston African Benevolent Society to support Black communities facing white resistance to integration.

Middleton and his wife, Elsey March, moved into the house at 5 Pinckney St. with Glapion, and when Glapion married Lucy Hawkins in 1793, the four of them apparently lived there together. This curious living arrangement, along with historic records and accounts, have led to the theory that Middleton and Glapion were both gay men, said Bagley, and as a result, their home at 5 Pinckney St. is the only building in the book with a possible LGBTQ connection.

“A challenge with unrepresented and unrecorded history is often the only way is to back-engineer and read between the lines,” Bagley said. “Unfortunately, that can lead to some guesswork and maybe even inaccuracies, but it’s the only way we’re going to come even close to getting there.”

Middleton and Glapion added two other buildings at 1 and 3 Pinckney St., respectively, which extended the structures to the corner of Joy Street – an area that was then, Bagley wrote, “the core of the free Black community in Boston.”

The two buildings later served as an addition to the men’s main residence at 5 Pinckney St., which, Bagley describes as a two-story wooden building with four bay windows that has the distinction of being one of 11 remaining wooden structures in a neighborhood made up largely of brick buildings.

In 1855, the three properties were transformed with the demolition of the middle structure at 3 Pinckney St. and its subsequent replacement with a four-story brick building similar in character to the neighboring row-houses.

In the 1930s, 5 Pinckney St. became the Pinckney Club, a private establishment, while 1 Pinckney St. was transformed, wrote Bagley, into “an Italian restaurant that catered to Boston’s bohemian residents.”

A private home today, 5 Pinckney St. is a Boston Landmark, as well as a stop on Boston’s Black Heritage Trail.

“The house wasn’t on my radar when I started researching with a list of buildings from the state,” said Bagley, who besides serving as the city’s archeologist since 2011, is also a Boston Landmarks Commission staff member. “I’d taken a photo of it, but wasn’t sure if it would make the cut. Then, I found the National Park Service website that put it in the 1780s, so that put it in the moment where it had to be in the book.”

As an archeologist, Bagley said he focused on the chronology of the properties from the time they were built until the present, rather than on their architectural elements, in his book. Still, he admits, it wasn’t always possible to determine the buildings’ exact dates of construction by examining deeds, probates and other available data.

And since only 13.5 percent (16,319) of the city’s 121,000 buildings had been surveyed for the Massachusetts Historical Commission’s historic building inventory as of the book’s publication, Bagley wrote, “some of Boston’s most hidden old buildings may have been missed,” so subsequently, his list of Boston’s oldest buildings might be altered or refined over time.

In fact, Bagley said prior to the book’s publication, he was sure to make his publisher aware that the list could eventually change, if previously unknown historic buildings are uncovered in the city, or if published information come under scrutiny as new findings come to light.

Bagley’s latest book, which he wrote as a companion volume to his first book, 2016’s “A History of Boston in 50 Artifacts,” begins chronologically with Blake House, a two-story building located at 735 Columbia Road in Dorchester that dates back to 1661, predating the city’s second oldest structure, the Paul Revere House in the North End, by around 19 years.

The Old State House (#7, 1713); Union Oyster House (#9, circa 1716); Old North Church in the North End (#13, 1723); Old South Meeting House (#16, 1729); Faneuil Hall (#18, 1742); the Shirley-Eustis House in Roxbury (#19, 1746); King’s Chapel (1750); the Warren Tavern in Charlestown (#31, circa 1780); and Memorial Hall in Charlestown (#45, 1791) all make the cut as well, and the 50th building on Bagley’s list is the Salem Turnpike Hotel at 16 Common St. in Charlestown, circa 1794.

When he was researching his first book, Bagley said he discovered an online inventory of historic buildings and was able to download a list of all of them in Boston, which he was subsequently able to narrow down by date. He then compiled a list of the 100 oldest buildings in the city and posted it online, and that soon gained traction.

“People liked it and shared it,” said Bagley of the impetus for his newest book.

Sue Ramin, director of Brandeis University Press, wrote: “The idea of writing a practical guide book that gathered Boston’s oldest buildings together in one place was as appealing as the book is useful. I loved the fact that it’s not only a guide book, but a reading book and a beautiful book to look at and browse in. And he took most of the photographs himself!”

Additionally, Bagley’s “unique perspective as an archaeologist gives us insight into the lives of these buildings, the changes they have undergone, and the efforts made to preserve them,” added Ramin.

Meanwhile, Bagley wants would-be readers to know his book doesn’t just focus on the 50 oldest buildings in Downtown Boston but instead covers the entire city.

“The buildings are not only downtown, but they’re all over the city,” Bagley wrote. “Nine neighborhoods are represented in the book. We hit Roslindale, Mattapan, Brighton, Allston, Roxbury, Jamaica Plain – they’re all in there.”

Joseph M. Bagley’s “Boston’s Oldest Buildings and Where to Find Them” is available at, as well as at local bookstores and from Amazon.

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