While docking in Edgartown to fill up on supplies, the venerable whaling captain James Longsail once noted, “You will no sooner find affordable lodging on Martha’s Vineyard than you will find a whale riding a bicycle.” Well, fifteen years ago on a hot August evening, despite Captain Longsail’s predictions, I did find a bed and breakfast that was not only affordable, but also accepted Saturday night–only stays and required no advanced reservation. Built in 1873, this Victorian town house was then run by the husband and wife team of Michael and Mary McCormack. It features thirteen rooms, each with its own private wash basin and toilet, a uniformed staff, and in perhaps the most unique feature of the inn, the McCormacks offered free car service that would pick you up anywhere you happened to be on the Island at any time. So while I have yet to spot a cycling whale, I will never forget the night I spent in that quaint place with the most peculiar of names – the Dukes County Jail and House of Correction.

An image of me lying in a jail cell on Martha’s Vineyard keeps flickering through my head. Nothing leads into the image – no flashes of an arrest or scenes of being fingerprinted. And nothing follows it. It’s just an isolated image playing over and over. Jail on Martha’s Vineyard . . . jail on Martha’s Vineyard. . . . It makes no sense. It’s like finding a stripper’s pole in your grandmother’s house. Jail is a place where bad people go to do even worse things to each other. Martha’s Vineyard is a place to load up on cocktails while enjoying an ocean view. Never the twain shall meet. Unless . . . this is all a dream.
    
Yes! Of course! This is one of those rare moments when I realize I’m dreaming while I’m still dreaming. It has to be. Martha’s Vineyard doesn’t even have a McDonald’s; how can it possibly have a jail? Heck, they don’t even have real cops here, just a bunch of college kids hired for the summer to make sure we don’t roll through stop signs.

So I open my eyes, confident – nay, almost cocky – that the absolute last place on earth I’ll find myself is in a jail on Martha’s Vineyard. In the upstairs bedroom of my parents’ home, nestled safely in bed? Probably. Passed out in Santa’s Workshop under a baccarat table? Probably not. Jail on Martha’s Vineyard? Never.

Holy Mother of God

I’m in jail on Martha’s Vineyard!

I close my eyes again and lie perfectly still. I’m not sure what I’m doing, but I think – and I’m not proud of this – but I think I’m trying to get back into my dream. “Of course, if this is still a dream, it’s now a dream of us waking up in jail after having a dream of us being in jail,” I point out to myself. “And I’m not sure dreams can break the fourth wall like that.”

Shhh, I have to sleep.

“We’re also hung over,” I say. It’s true. My clothes are damp with sweat, a dried trail of drool runs from my cheek to my ear, and my brain feels like someone is taking its blood pressure. “Can people be sweaty in their dreams?”

Stop thinking!

But it’s useless. I’m awake and I’m not falling back to sleep. I open my eyes again. I’m lying on a red mat in a cell that looks just like the ones I’ve see on TV – about six by eight feet, with three walls of chipped cinder block and one wall of heavy iron bars. There’s nothing Vineyard-y about the place. No teak. No scrimshaw. No “I’d rather be playing tennis” embroidered pillows.

My next thought is that my parents are going to kill me, or at least never let me use their place again. “My house, my rules!” is what my dad always says. And while I’m sure that his list of rules, which includes “Leave clean sheets on the beds,” “Replace any food you eat,” and “Put MVY dump stickers on all trash bags,” doesn’t specifically make mention of “Don’t get thrown in jail,” I’m also pretty sure that it’s implied.

Then I think, “What the hell am I thinking?” I’m in trouble here, and not the “I-hope-my-parents-don’t-find-out” kind of trouble, but the “Get-my-father-on-the-phone, I’m-in-trouble!” trouble. I’m locked up, in the can, the joint, the pokey, up the river. Granted, it’s on Martha’s Vineyard, but jail anywhere is serious. And – and this is a very big and – I still don’t know what I did to get here.

The last thing I remember, I was sitting on our porch, enjoying a bottle of Southern Comfort. I was with a friend. The friend left. I opened another bottle and . . . poof! . . . I’m here, which leads me to believe that either, (A) The Martha’s Vineyard police are not only real, but an elite corps of highly trained ninjas who creep onto people’s porches, knock them unconscious, and drag them off to jail, or (B) I drank so much that I blacked out and subsequently did something really, really stupid.

Unfortunately, the answer is never (A).

I lean my back against the wall, pull my legs toward me, and rest my forehead on my knees. I close my eyes, peer into the darkness, and imagine that I’m in outer space, surrounded by nothing but quiet and blackness. I’m trying to go back in time, trying to remember anything that might have happened between that second bottle and jail.

Anything. Anything at all. Anything.

Then I hear it, a voice, distant and muted: “The Inn.”

I immediately recognize the voice as Last Night Me: “We went to The Inn.” Yes! I want to grab Last Night Me by the collar, shake him, and say, “Tell me everything!” But I can’t. I know the drill. He’ll shut down. Last Night Me needs to be coaxed and coddled. At night, he might be this crazy uncle on speed, getting into fistfights and dancing on tabletops, but in the morning, he’s Slothful Sheepish Man-Idiot. Think Lenny from Of Mice and Men, which, unfortunately, makes me George.

“What happened at The Inn, Lenny?”

“Ummm . . . I remember there was a guy with a moustache, George.”

“What about the guy with the moustache, Lenny?”

“He was angry, George.”

Oh, this is not good. This Inn employs a bunch of college kids for the summer. Two years ago, I partied with some of them in their living quarters. It was a lot of fun. Of course, I had also been invited and there had also been a party.

“Well, no kidding he was angry, Lenny. You were trespassing! What else can you remember?”

“There was a guy with a moustache, George.”

“Yeah, I know about the guy with the moustache. What else?”

“He was angry.”

Argh! That’s it. That’s all I’m going to get from Lenny/Last Night Me: (1) I went to The Inn, (2) An angry guy with a moustache was there, and (3) Now I’m in jail. I just need to fill in the blanks. It’s like doing a Mad Lib: I went to The Inn. Angry guy with moustache. Now I’m in jail.

 I went to The Inn and made an ass of myself. Angry guy with moustache called the cops. Now I’m in jail.

Given my situation, this is probably the best-case scenario. Talk about your low expectations: I hope I made an ass of myself. And I really do hope this, because the other possibilities only get worse.

I went to The Inn and stabbed angry guy with moustache. Got arrested for manslaughter. Now I’m in jail.

I doubt I did something this bad, but it’s a possibility. That’s one of the drawbacks of blacking out – you don’t 100 percent know. My sole defense to any accusation lobbed against me is, “That doesn’t sound like me.” But really, until two minutes ago, barging into The Inn drunk didn’t sound like me either. Until six months ago, trying to steal a bulldozer and drive it down Newbury Street in Boston didn’t sound like me. Nor did throwing a TV through a hotel window or peeing in the corner of a Yo-Yo Ma concert. Yet apparently I did all these things, because apparently when I’m drunk, I’m quite the idiot.

“Oh, God, please let me have just made an ass of myself,” I catch myself whispering. “Don’t let me have done something really bad.” It feels weird to be praying, but I have to. I can’t get sent off-Island to a real prison. I won’t survive. Some lifer is going to ask me, “Where’d you last do time, boy?” and I’m going to have to say, “Martha’s Vineyard.” He’ll kill me. (Well, first he’ll make me his wife, then he’ll kill me.) I have to remember to at least say Dukes County. “I did a stint at the Duke,” I’ll growl, making sure to add, “and remember, that covers not only the Vineyard, but also the Elizabeth Islands as well.” He’ll kill me quicker.

“Rise and shine.” It’s another voice. This one is loud, authoritative, and definitely not coming from inside my head. It’s a cop. I can see him through the bars. “Oh, please, God, let me just have made an ass of myself,” I start up again. “I promise to never drink like that again if you just please let me out of here. Please. . .please. . . .”

“You ready to start behaving?” the cop asks. I nod. He unlocks the cell door and motions for me to step out. I follow him down a corridor to an admitting desk. Two more cops are there. I hear something about “protective custody” and “no further consequences.” I sign a piece of paper. I have no idea what it says. It could be the deed to my parents’ house. I don’t care – “Enjoy the view, officers!” – because for the first time in nearly seven hours, I’m a free man; and despite being asleep for all but thirteen minutes of those seven hours, I’ve learned lessons to last a lifetime. Thanks in part to the Dukes County Jail and House of Correction.

The End (sort of).

I really wish that “last a lifetime” line was true. It would have made a nice ending to what’s essentially a coming-of-age story. Unfortunately, upon walking out of jail, I found myself in Edgartown. And while the police might be happy to pick you up anywhere you happen to be on the Island (in my case, I was in Vineyard Haven), they aren’t too keen about dropping you back off. So I was forced to hitchhike home.

“That is awesome,” said the guy who picked me up, after hearing about my night of incarceration. Then he leaned behind the passenger seat, reached into a Styrofoam cooler, and handed me an ice-cold beer. “Welcome back to society, man.” And that’s when I realized one very important thing: I had a jail story. Cool! In fact, to be a man – a real man – you have to spend at least one night in the can. It’s called earning your stripes. I pity the boy who doesn’t have a jail story. He probably pees sitting down, too.

Twenty-five minutes later, I was dropped off in Vineyard Haven. It was 8:30 on a Sunday morning and I was already three beers in. And unfortunately, it would be another four years and one major incident involving two bouncers, my head, and a New York City sidewalk, before the lesson of this story would finally (finally!) last me a lifetime.

The End (hopefully).