Downtown Windsor

The March 2016 issue of FLASHBACKS, “Peak Windsor,” looked back at the history of Windsor’s hilltop. After the issue went to press, I spoke with John Boyle, now of Dalton, who grew up there after his father bought the now-vanished Berkshire Trail Café. What follows is an edited and illustrated version of our conversation. Susan Phillips

John Boyle: “My father acquired the property in 1946. The tower was already gone by then, I don’t know what happened to it. But the footings are still there.

“The business was called the Berkshire Trail Café. My father owned it with my mother from 1946 til the early '60s…it was a basic roadhouse. People were just starting to fully engage in driving automobiles in the late forties early fifties. People would come up out of Adams and Pittsfield and drive up to these roadhouses. They had them in Savoy, Windsor, Hinsdale...a lot of the hill towns. There aren’t many left.

“There was a pool table, bumper pool. The TV, that was a draw. Then there was a jukebox, and beverages. That was about it. We didn’t serve food.

“The Volskys lived nearby, and they were regulars. Olive Volsky painted the mural behind the bar. It was a big painting. On one side, there was a picture of a huge bear. The bear was standing upright on its hind legs, with a deer that had just been slain at its feet. On the other side were a couple of Indian braves. It was kind of a stand-off. Who was going to get the deer?

“Growing up, I didn’t hang out in the café when it was open, that wouldn’t have been allowed. But we did live there, in the apartment upstairs…And I went to Crane Community School right there across the street. I remember a friend telling me years later, ‘I used to envy you because you lived downtown.’ Downtown Windsor! Me and Ken Estes, we were the lucky ones, we never had to ride the school bus.

“After the Crane School, I went to Dalton High, we were the last class to graduate from the old high school in 1961.”

Boyle told me his parents sold the café and bought the residential property next door at 35 Savoy Road. They sold the café to a group of owners who operated it under the name The Alibi for four or five years. After the business closed, the building was abandoned for some years, until Henry Estes acquired it and had the Windsor Volunteer Fire department burn it down for practice in 1973.

I would love to know more about the Berkshire Trail Café and its later incarnation, The Alibi. The business must have played a big role in our community, as a central gathering place for residents and visitors from nearby towns. If you have memories or pictures to share, I will add them to the story.