Christopher Gray, historian, writer, avid letter writer to the Gazette from the Republic of Chappaquonsett, and for 28 years the author of the popular Streetscapes column in The New York Times, died on March 10. The cause was complications from pneumonia. He was 66.

His letters weighed in on matters weighty and small, from his love for “the blue green stains in our sinks” to bicycle safety and humorous swipes against McMansions. In one letter he suggested that the Vineyard adopt less standard road signs to combat speeding. “We need entirely different signs, like, This Road Established 1844 — What’s Your Hurry?”

The first Streetscapes column appeared in 1987 and it was quickly apparent that this was much more than fodder for architectural nerds. Mr. Gray’s subjects ranged from the Harvard Club to the history of traffic lights, from courthouses to row houses, from grand dame buildings to eyesores. Taken together, appearing every Sunday in the real estate section, they represent both the timeless and the passing of time in New York city, breathing so much life into the urban landscape that it rivaled the teeming masses who lived there.

In Mr. Gray’s own words, appearing in his final column on Dec. 26, 2014, he described his decision to take the job this way: “Rather than take up the work of a poet or a cabdriver, I decided to go for the big money: architectural history.”

In a column about the Empire State Building entitled Not Just a Perch for King Kong, he described how in 1929 a group of investors floated the idea of docking dirigibles, some up to 800 feet long, by tying them to the top of the tallest building in the world at the time. The idea never really got off the ground, and New York was saved the trials of having the Hindenberg float high above midtown.

His column on the history of bathtubs and bathing in the city began this way: “The evolution of personal sanitation in New York was slow. Mary Mason Jones, a distant relative of Edith Wharton, is said to have had the first bathtub in the city in 1818, in her house on Chambers Street.”

He could also dive deeply into the vocabulary of architecture like no other: “The anthemion and its close cousin the palmette together constitute the secret handshake, the coded lapel pin, the whispered password of the resurgent classical movement.”

Christopher Stewart Gray was born on April 24, 1950 in Kansas City, Mo. When his parents divorced, he moved to New York city with his mother, getting an early education in his life’s work just by walking from his home on 56th street to school or visiting his mother’s office at Harper’s Bazaar. As an adult, before turning to writing and researching, he worked as a seaman, a cabdriver and a substitute mail carrier. He graduated from Columbia in 1975 with a bachelor’s degree in art history. Soon after he opened the Office for Metropolitan History and later began writing, first for Avenue Magazine and House and Garden, and then for The New York Times.

Fittingly, he met his wife Erin thanks to a bit of historical architecture.

“I was a student,” she said, “trying to save a building from demolition. I wrote some articles on it, included my phone number and asked if anyone wanted to help me with it. Christopher called and offered to help. The building, which was originally the New York Cancer Hospital and at the time was the Towers Nursing Home, still stands today.”

The couple married in 1980.

Erin Gray, maiden name Drake, had ties to Martha’s Vineyard and the couple enjoyed summers at their seasonal home off Lambert’s Cove Road in Vineyard Haven with their children Peter and Olivia.

“This was his happy place for sure,” Erin said. “He wasn’t a beach person or a classic sportsman. His idea of a nice Vineyard day was reading on the screened porch. And we used to row out on the water to see the sunset.”

He also traveled about the Island in a classic 1950 Studebaker. More than just a taste for classic cars, this was a nod to family: Mr. Gray’s grandmother was a Studebaker.

Christopher Gray leaves behind a large body of written work. In addition to his columns he wrote several books. However, words alone were not enough for him. He also left his bones.

In an unusual move, something that surprised even his family, he bequeathed his skeleton to his high school alma mater, The St. Paul’s School. This is not as easy as it may sound.

“I thought he was kidding,” his wife said, referring to when he first brought up the idea about a year before he died. “But then he got me and the children to sign off on the idea.”

First the family checked with St. Paul’s to see if they actually wanted Mr. Gray’s skeleton. The school was enthusiastic. But then came the problem of the particulars.

“This was a relatively new topic for me,” Mr. Gray’s wife said. “Christopher had suggested using Skulls Unlimited International. There really is such a thing. But they wouldn’t do it.”

In the end the Smithsonian stepped in to help with the procedure and is monitoring the process. The hope is that everything will be ready by next June, which would coincide with Mr. Gray’s 50th reunion.

“It’s a part of the continuum I guess,” Erin Gray said. “But what that really means I don’t know.”