I was asked by the editor of Stockbridge Updates to write my memories of growing up and living in Stockbridge. During most of my teen years, I was at boarding school. My college years were spent at a tri-semester college in Iowa. It was in Iowa at a drive-up burger place when I changed my mind about never returning to Stockbridge. 

My roommate, Charlie Allen, asked me, “Did you hear what that guy just said on the radio?” I said I had not and he said, “This guy said, ‘Let me tell you about the town of Stockbridge Massachusetts’.”

I told him he must be mistaken. Stockbridge was nothing more than a run-down hotel only operated in the summers and a bunch of entitled grandchildren of old rich people.

I did eventually hear Arlo Guthie’s “Alice’s Restaurant.” Curious, I returned to my hometown in February 1969. I ended up working at the newly re-opening Red Lion Inn. Stockbridge was much different town from what it is today.

There are thousands of memories I have of Stockbridge during the late sixties, early seventies and eighties. As I think back, one rises to the surface first.

I was reluctantly bartending in the Lion’s Den. One evening before it became busy, off-duty Police Chief Bill Obanheim and his fellow officer Eddie Iacobucci (sp) bellied up at the bar. They ordered their standard favorite Seagram’s Crowne Royal and Seagram’s 7. 

After a while they were ready for their third drink. The phone behind the bar rang. I picked it up and assured the caller they had reached the “Lion’s Den.” 

I listened and told the caller, “Hold on.” I stretched the cord down to where Obie was sitting and handed it to him. 

He said, “This is Bill.” After a silence, he yelled, “They did what?!” He said to Eddie, “We need to go!” They downed their new drinks and left.

Now this was a time before marijuana was legal. Earlier that day Officer Obie’s son Billy had been arrested for growing weed behind a Select Woman’s house in town. What happened next is a friend of Billy’s got into the Police Station, took a shotgun, and blasted open the locked door to the one cell in the Town Jail. They both escaped and have never, to this day, been apprehended. That is the story of the one and only Stockbridge jail break.

I also urge others who grew up here to contact Carole Owens at Stockbridge Updates. I am sure their perspectives are different from mine, and their memories and stories deserve telling, if for no other reason than to give current day residents some perspective on what came before their time here.

Editor’s note: As the village grows and changes, SU is asking all of you to submit a Stockbridge story. We had something special here. It was, indeed, Stockbridge exceptionalism. While we may not be able to hold on to it, we can record it for posterity — as the saying goes.