I have lived most of my life on the right side of the law. I say most, because almost all of my alternative encounters with law enforcement have come on Martha’s Vineyard. It’s a ‘record’ stretching all the way back to my teenage years. I don’t know why this happens. Perhaps it’s about summer vacations or driving habits honed on Island roads, or just being in the wrong place at the wrong time. But there it is.

When I was 17, I was eager to show off my Dad’s 1967, yellow and black Camaro and its lusty 327 engine. With a stick shift on the floor and a now-classic, road-racing look, it was a muscle machine that I had little understanding of. Standing outside the Casino at a West Chop dance that summer, I saw my friend Freddie Johnson and offered to take him on a ride around the West Chop loop. The result: a ticket and a blurb in the police reports in the Vineyard Gazette.

Another encounter, which never made the news, involved another of my father’s pet cars. The year was 1965. It was summer and my license was new. I offered to take my sailing friends Margie and Carol up-Island in my father’s 1959 powder blue, Mercedes 190 SL convertible, another future classic car. As we breezily moved top-down into Chilmark along Middle Road all traffic had disappeared, so Margie and Carol hiked themselves up onto the back of the car and dangled their legs down onto the seat. A police car suddenly appeared in the rear view mirror, so I quickly turned up a long driveway going up far enough so that Middle Road nearly disappeared, and turned off the engine.

The police car whisked by. We sat and waited a bit, then I backed down to the road and smartly turned to the right in the opposite direction of the dreaded cruiser. Minutes later, though, I was handing my license to an intense Chilmark policeman. He looked at me straight in the eye, and deeply intoned: “Son, I know every driveway in Chilmark, and you don’t belong in any of them. Your registration please?”

I didn’t have it, my father did. The officer, not amused, said, “Meet me back here at Beetlebung Corner in an hour with that registration or you’ll be in deep trouble.”

I returned home to Vineyard Haven in a panic. How was I going to get the registration from my father without causing an inquisition? I walked into the house trying to appear calm as a sunny day, but inside was a tempest. After some casual conversation, I gently suggested to my father that perhaps it would be a good idea to have the registration in hand. With his dad instincts suddenly on high alert, he bellowed: “What happened?”

“Oh, Schuyler!” my mother said. “Don’t be so suspicious!” She drew out the last word with a dramatic emphasis (SUS-SPI!-shus) so much so he immediately quieted down.

Reprieved, I quickly accepted the sacred card, shoved it in my pocket and ran back out to the car.

“Picking up Margie again,” I yelled.

I had just enough time left. As I eased the Mercedes up to Beetlebung corner, there was the cruiser with the Chilmark officer leaning up against it. I gave him the registration and left with a stern warning.

Most memorable, however, was the police raid on the house I was living in during the summer of ’69. Located on the corner of State Road and Look street in Vineyard Haven, it was ideal summer living for college kids. Instead of paying room rent, we each paid $12/week for a bed. The beds were everywhere — in the dining room, the attic, even the garage in which the owner put concrete down on the dirt floor and popped in a few more bed frames. At all hours of the day and night there were upwards of 15 to 20 kids there who spilled out onto the front porch, the lawn and second-story porch. And it being the 60s, rumors quickly flowed about marijuana and other sundry ingredients in use. Which there was.

The summer continued smoothly until early August when, while sitting in the kitchen, I heard sirens and saw flashing lights surround the house. It was a police raid and our house was one of five residences searched that night. People panicked and started flushing toilets, throwing things out the windows and racing around not knowing what to do.

I was ordered to go to my room on the third floor where I had to put my hands up on the wall and was frisked. Next, my suitcase was turned upside down on the bed. My roommate remarked to the officer, “Don’t worry, he’s a tennis pro. You won’t find anything there.”

And indeed, as the officer shook the bag, out tumbled sweat socks, jocks, shirts, shorts and tennis balls. The cop looked at me disapprovingly, dropped the bag on the bed and walked on to other rooms.

Most people survived the night, and the following week, while half the house left for the three-day music fest at Woodstock, news about the Island-wide raids appeared on the front page of the Gazette. I moved out and went to the house of a friend in Oak Bluffs and lived there quietly for the rest of the season.

A year later, though, the final chapter to that overflowing episode appeared in the movie Woodstock. There, up on the big screen, as I sat in a darkened movie theatre in Philadelphia, was one of my Island friends, Sue S. Her radiant face filled the entire screen, her sun-streaked hair cascading down to her shoulders in curls framing her face as she smiled a wide, innocent smile that summed up all that was good and beautiful about that youthful summer — an image burned into my imagination that 55 years later lives there still.

David Lott lives in Vineyard Haven.