Years ago I wrote a column about my notorious, crazy and fearless water-borne antics as a teenager. Most of these occurred in a 1960s-vintage Boston Whaler in and around Marblehead Harbor. And most of the negative outcomes from my antics were due to excessive speed. Fortunately – for a while, anyway – my friends and I, like Butch Cassidy and the Hole in the Wall Gang, escaped the authorities by zooming away into remote coves and hiding amongst the zillions of other white 13’ Boston Whalers in Marblehead. My dad had a good idea who “Butch” was, though, and finally put an end to my nefarious activities by painting a diagonal red stripe down the side of my Whaler. My days were numbered.
Adulthood brought with it a slightly heightened degree of risk aversion on the water. But there was the occasional incident where things could have gone awry, and, but for the grace of God, didn’t. Here’s one from 25 years ago:
1. Five men, in the dead of winter, wind blowing 15 knots from the southwest, sailing a 15’ Bullseye sailboat three miles across open water to spend the night on an offshore island with an exposed pier and no float.
It seemed like a good idea at the time.
And it was amazing how much freeboard we had, even with all our gear loaded “below decks.” Our gear? Food, warm clothes, even a guitar. We knew no one but the caretakers would be on the island in the winter. And we knew there was no float out there, as there was no harbor. So we towed a tired Bombard inflatable, figuring we’d pick up a mooring off the pier and ferry each other and our gear ashore.
It seemed like a good idea at the time.
We learned that when hands get wet in winter they don’t work very well. We learned that there were no pennants on any of the moorings, and that rigging a line was slow work with numb hands. We learned that getting from a loaded-down daysailer into a partially uninflated inflatable in a rolling sea and hanging on with numb hands was difficult. We learned that using those same numb hands to row in with half the crew was possible, but only because it was downwind. And we learned that rowing back alone was seemingly impossible, but one of us did it just the same. And, finally, we did all this because in our rapidly maturing minds we realized that we had no choice, as the daylight was leaving us and it would have been a wet, interminable, upwind slog back home in an overloaded boat.
We all stood shivering on the lonely pier and looked back at the little boat as it bounced in the rolling seas. “You’re sure you can get into Steve’s cabin, Dave?” someone asked, shivering. “Otherwise, long night out here. This place looks abandoned.”
“And what if it blows up even more tomorrow?” someone else said, looking at the bedraggled Bombard perched on the top of the pier. “How are we going to . . . ”
“You don’t ask those questions,” I said.
Our sodden expeditionary force turned to trek up the long pier and head across the island to where we knew Steve’s cabin was situated.
“Jeez, someone’s here, walking toward us,” one of us said.
“It’s Jack,” someone else said, laughing.
“Who?”
“You know, from ‘The Shining.’”
“Don’t creep me out.”
It was the caretaker. “Been watching you through the binoculars,” he said as we got face to face. “Couldn’t believe my eyes. Little sailboat out this time of year. Couldn’t believe my eyes.”
“We have permission to stay in Steve’s cabin,” I said.
“Okay. Why don’t you come into the caretaker’s house and warm up, first. It’s a half mile across the island to get to Steve’s.”
So we went in. The caretaker was silent, and acting a bit odd, kind of tweaking his head a bit, eyes fluttering occasionally.
“Could use a drink to warm up after that,” I said, mostly to make conversation. He didn’t look at me at first, then turned and stared into my eyes.
“Drinking and being alone out here don’t mix too good, I found,” he said. Out of his earshot (I hoped), some of our crew were making “Here’s Johnny” comments to each other. “So you’re alone?” I asked. “Alone out here all winter? I thought it was a couple caretaking.”
“There was,” he said. “Didn’t work out. She lost it. Had to be taken off,” he said as we entered the main room of the cottage. The first things I noticed in there were handwritten sheets of paper everywhere. And I mean EVERYWHERE. I sauntered over to one clump of pages and peered down, nonchalantly trying to decipher the writing. He saw me.
“Trying to figure out what happened. Writing stuff down,” he said. “Trying to get my head together.” Then he sat down by a stack of his papers, tuned us all out, and became absorbed in the contents.
“Oh,” I said. “Well, we better mosey along before it gets totally dark.”
Two of the crew made head gestures at me, meaning “Let’s get OUT OF HERE.”
And so we trekked to Steve’s cabin, got in okay, lit a fire, cooked dinner, had cocktails, and Joel played his guitar. It sounds relaxing, doesn’t it? Five good friends, all secure in a cozy log cabin for the night. Nothing out there but the sound of the wind whistling around us, the shutters chattering. Nothing at all. Except the caretaker.
“Here’s Johnny!”
Dave Roper’s new novel, “Rounding the bend: The Life and Times of Big Red,” was released in mid-June and is available from Amazon.com and Barnes and Noble.



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