The Blowout Sail, or: A tale of the greatest race on Earth

Originally written in spring 2005, Milan, Italy. Revised October 2019.

I’m sure there are many civil, gentlemanly model boat races on calm inland waters throughout America. Chrysler-driving old men and cornflake-fed children in Polo shirts gather on a lichened pine dock to launch factory-painted balsa sloops and ketches, tending them with sticks and perhaps a radio controller. At the drop of a flag, the craft totter and slurp through the wavelets to a pink mooring ball, arriving in a tidy flotilla of white nylon sails and politely wagging telltales. Golf claps and spilled lemonade are the only action from the sidelines.

The Annual Whippoorwill Yacht & Rocket Club 1-Meter Challenge Commodore’s Cup at Menemsha Pond on Martha’s Vineyard was of a different ilk. There were no store-bought models at The Boat Race, as we called it, and nary a telescoping antenna was to be seen. The waters were spared the wake of propellers and jet drives. None of these things were allowed. But anything else was–anything.

The home-brewed craft of the 1-Meter Challenge were on their own, under power of sail, when The Gun went off and the skipper released their hold on backstay and shroud. It was a matter of sheer ingenuity versus the chaotic forces of Nature, a fiendishly magnificent tango of Man and The Elements as each duct-taped yawl and Kryloned catamaran slogged across that salt pond one way or another on Columbus Day weekend. We skippers, and our very pride, were at the unfettered mercy of the deep. The Chrysler drivers did well to steer clear.

And O, that Gun. Police Chief Tim Rich showed up every year with his carbide cannon and enough shot to start the races and invade the Comoros in one go. Once this blunderbuss rang out over Menemsha Pond, every set of ears from Devil’s Bridge to Duxbury knew a heat had begun. In my kid years, I would run and hide behind a nearby pickup truck when I heard the call of the bullhorn, my Old Man hollering, “ready on the line!” The ensuing blast was a punch in the vitals. I feared the gun as a child. I revered it as an Adult.

Every year, The Boat Race saw wilder and wilder nautical concoctions as kids and adults alike went to astronomical lengths to eke the most they could out of the fall breeze with as little monetary expense as possible. The auburn sands of Menemsha Pond’s Red Beach would be crowded with craft christened Dumptique and Legobeast. Some remained nameless. Seagull feathers stuck into a piece of former styrofoam cooler, A&P shopping bags with locust twigs as spars atop lashed-together soda bottles, and all manner of plastic window insulation and Saran Wrap found their way to Red Beach.

The hardcore salts, usually old-time Vineyard beach bums who wore wetsuits under their Sunday bests and whiskered former longliners who had seen more presidential administrations than movies, would show up with laboriously hand-wrought craft of uncanny detail and incredible prowess over the water. Folks of the plastic-bottle school would ooh and aah as they cleared a path. Wetsuited kids clambered in and out of their fathers’ rusty panel vans and through the tall grass in excitement.

The run-up to Zero Hour was a contagious mania as the north wind bit our noses and made our flip-flopped feet and bathing-suit-clad legs shiver. The veterans would mosey about the sand, recalling Races past with kindred spirits. The kids ran down the beach and basked in it all. On Race Day, theirs was a playground like no other child in the world had. Classic Vineyard, the real old guard. We were all nutcases. Good nutcases. Somebody always had a good story about someone else from way back when. No one was jealous or scornful, there were no ugly rivalries. Down-islanders, off-islanders, no matter. They were all as good as family. For that long-awaited Sunday in Gay Head, everyone was a friend, everything was allright, and we were all equal, no matter what we brung.

For every ten zany new creations that graced the shoreline that day, there was one hale-and-hearty veteran craft. In particular, the WYRC/John G. Early Contractor and Builder entry Udder Shock, a foam-hulled catamaran skippered by the wily old Eric Ropke, had seen year after year of brave yet unsuccessful participation. Her name derived from the twin rudders cut and painted to resemble bovine anatomy. The John Early crewmembers were surpassed only by Molière for their highbrow humor. Shock was never an odds-on favorite, but on the line, she was an institution.

I had in my corner a strong contender. Having earned my share of victories in the Children’s class in years previous with my brave and storied sloop Day-O, winning many a free half-pepperoni/half-cheese pizza from Primo Lombardi’s Chilmark Store, entry into the Adult division meant I had to likewise up the ante. Pop and I had pored over the bandsaw for hours on end, with five-minute epoxy and Elmer’s wood glue crusted on our fingers, pink styrofoam dust in our scalps, as we created my new craft. She would be christened Triumph. A sloop-rigged trimaran of exactly one meter LOA, her triple-layered polystyrene hulls sealed to a fine sheen with clear epoxy, her top decks finished in matte black Rust-Oleum, her sails made of lightweight mylar, she would be a force to be reckoned with on the pond.

Triumph’s maiden voyage in 1995 was less than spectacular. First-revision bugs led her left, right, even in reverse, and out to the middle of the pond in various heats, at the mercy of the chase boat. A meager fourth-place final standing was all I could muster in her first year; not even good enough for the free sundae at Cozy’s. I had to improve if I was to uphold my reputation. I had by then gained real piloting skill in the crucible of competitive sailing, and my knowledge of points of sail and seamanship were harpoon-sharp. I meticulously analyzed Triumph’s behavior under all sorts of conditions, tweaking the set of her sails, the angle of her rudders, and the weight of her ballast. Every so often, she summoned the power of fire and brimstone, tearing like a mad Rottweiler from my hand, toward first-mate Jesse’s waiting grasp. Any victory I enjoyed was shared with him, my perennial sidekick on the line. As the race seasons passed and Triumph improved steadily, we would test and re-test there in the razor-edge grass of Red Beach’s shallows, until we were sure she was ready. In that year of 2000, we were prepared to accept all comers.

We would be on a stiff beam reach that day, my favorite point of sail. Triumph was at her best there, her three hulls cleaving the spitting waters as her red and yellow sails filled and threw her forward on a vicious streak. The damp mid-autumn air tumbled over the dunes and smacked the water’s surface. The souls gathered along the great long finger of road to Red Beach, pickup beds displaying proud efforts. The Old Man was hard at work with the other race officials, dividing every entrant into one heat or another. Participants strolled the russet shoreline, inspecting their competition and needling one another. Some donned waders to ward off the sting of the seaweed-clogged water. Herbie sat at the registration table down on the sand, handing out the number decals. Triumph was Number Eight.

Electricity was in the air now. The Chief was downshore with The Gun, ear to his two-way radio, awaiting the first heat. Mothers sat on beach blankets on the chilly sand with coolers of sandwiches and Coca-Cola. At least forty tales of the ‘70s had already been told. Nylon string was carefully wound and unwound from cleats fashioned from brass screws and eyelets—the final adjustments could make or break a heat.

For some, those last tweaks could mean the difference between a life of anonymity among the motley roster of skippers, or a legacy of eternal glory etched in shining brass. To the overall fastest craft across the line that day would go the prize of Line Honors, with a sizable monetary and alcoholic purse. More importantly, though, the skipper’s name and year of victory were emblazoned on a brass plaque affixed to the hallowed Commodore’s Cup. It was a beautiful wooden sloop on a stand, once owned by the late, legendary WYRC Commodore Gordon Otis, the story of whom was written in Bacardi and brown acid on the pages of Vineyard mythology. To have one’s name on The Cup was to be ordained to the highest order of reverence by Gordo, the God of Good Times himself. At the commencement of every Challenge, a solemn dedication and moment of silence was given in Gordy’s honor, sailor and spectator alike knowing that he would look down and see us through another one. I had no ambitions of my name gracing The Cup; it was the domain of the elders, the salts, the Big Dogs. I was too green yet. Or was I?

Jesse and I had butterflies the size of Cessnas in our stomachs. The Star-Spangled Banner was sung by a local voice, the spectators wound up in anticipation. Triumph was calibrated with the precision of a space vehicle rendezvous. Her mylar sails luffed loudly as she sat in her cradle, her popsicle-stick weathervane twiddling on its spindle.

The first scrappy heat of the Adult Monohull class stood in the piercing cold pond, perpendicular to the shoreline, a great tableau of plastic, canvas, and wood stretching out into the turbid water. Plovers and gulls swooped overhead. My Old Man stood at his official post in the parking lot overlooking the beach, bullhorn in hand. The race officials encircled him, clipboards grasped in trembling and wind-seared hands, VHF radios poised for signals from the chase boats and finish line. John Early radioed to Chief Rich to stand by. The Old Man raised his horn. “Skippers, ready on the line!” A pause. Muttering on the VHF. Nocturnal silence.


The Gun went off with a rib-socking report. The first armada of styrofoam sloops and balsawood brigs careened, meandered, and luffed their way down the course. Spectators crowded the seaweeded tidal pools of the shore while cameras clicked. A bellowing obbligato of whoops and hollers accompanied every capsizing and loss of course. Bottle rockets went off. Hot glue seams gave way, masts came unstepped, shrouds snapped, feathers flew, booms slapped back and forth in the fitful puffs. Men groaned in anguish and the chase boat dashed after the wayward craft. The race was on.

Heat after heat burned on, until finally the multi-hullers were called upon. The first heat saw Triumph turn in a formidable performance, an easy 2nd place finish, soundly securing my slot in the elimination rounds. First-mate Jesse and I were feeling good.

Then, without warning, the heretofore cooperating wind shifted ninety degrees to the east. Boats on the course went wild, unable to fill their sails with the direct headwind no matter how close-hauled they were. Good Lord, what were we going to do? The officials scrambled for a solution. Hastily, they reconfigured the course to head away from shore rather than run alongside it. But not only had the wind shifted, it had picked up considerably. The chase boat would have to be particularly deft, lest any rogue craft boom on for Quitsa or the dreaded tidal currents of the Menemsha Channel. The deciding heats were on, and the skippers frantically recalibrated their rudders and sheets for severe conditions. Jesse and I staggered back and forth in the shallows, doing our level best to re-set Triumph. The Old Man advised the use of the storm jib, which we tied off and set in record time. The moment was at hand.

The tension was thick like a summer morning’s fog rolling across the beach. Teeth chattered on the line as we awaited The Gun. Eric and Udder Shock stood beside me at the ready. Her war-torn paint finish and rusty fittings spoke volumes of the battles she had fought so valiantly. Though ornery, she was light and swift, and under the right conditions she would be a worthy adversary. We stood, set like steel traps.


It was as if Gordo had come down from the clouds and tied our boats to the bumper of his ‘65 Chevy Impala and sent it all the way. Udder Shock and Triumph tore from our grasps with an unprecedented vigor. The two had at last met one other’s match. Triumph never hesitated, her sails ballooning and pushing her forward with all the energy of a Niagara power station. The two of us had a commanding lead over the rest of the field. As the two craft rocketed towards the finish, it became harder to tell which was in front. As time crept onward and the two multihulled demons struggled for glory, it appeared that Triumph had gained the upper hand. Sweet Jesus, this could be it. Shock did not give up by any means, though. If I were to win, it would not be by much. My Triumph had to throw down as much thrust as she could gather. Her sails were set for a close reach. Her rigging creaked and vibrated under the relentless October wind. She was a thunderbolt. This was it, the home stretch.

And then, calamity. Just on the verge of the finish line, Triumph’s storm jib exploded violently under the pressure of the howling easterly wind. The bursting of mylar echoed across the pond. My jaw was agape. Gasps and moans. At the last second, she lost just enough momentum to yield the checkered flag to her arch-rival. Triumph had taken a noble second place, going down in a blaze of glory. She was taken back to shore by the chase boat, her jib shredded, decks covered in salt spray, hardened from the fiercest race she had yet seen. I was proud.

But the saga was not over. After all the prizes were handed out, every large pizza and dinner at the Home Port awarded, it came time to announce Line Honors. There were the usual rumors of past champions taking the prize; Spa Tharpe, Ridge White. Not this time. The Old Man read the race report. The winner, he said, had registered the fastest time across the line in the entire history of The Commodore’s Cup. Jesus God, who could it be?

“Eric Ropke and Udder Shock!”

The crowd went berserk. No one could believe it. Eric had done it. Gordo had chosen him. After so many years of Runner-Up, Udder Shock was now a coronated Victor–and the one to rule them all.

Triumph had stared down the barrel of Fate that year. A mere whisker of distance, a shred of mylar, and a good dose of Fortune’s wiles had kept her from legend in the annals of the Yacht & Rocket Club. Though I was happy the Cup would stay in the WYRC family that year, I was in a state of incredulous lament. So close. We pondered what might have happened if, if, if. We knew that it was the Commodore telling me to keep the faith, that one never knows which way the wind will blow at Red Beach.

The pickups and wagons were loaded up with another year’s troupe of skippers and craft, off to celebrate somewhere in the woods of Gay Head, drinking to the victory and the tragedy, the lore and legend of the Race. The Gun would lay silent for another year, the waters of the pond would lap gently at the lobster buoys and daysailers. Summer would come and go. We nutcases had another year to add to the great storybook, another year to recall wild tales of yore, another year back in drydock. Our grand symphony of sail and mast, of cries from the shallows to a runaway boat and ecstatic cheers as another one crosses the line, the choruses of father and son, of sister and brother waiting for the roar of The Gun, the ballet of hulls on the foam, the primeval duet of two crafts bow-to-bow racing to the end, as ever, would be back.

Postscript: Triumph would go on to win Line Honors at the 2006 1-Meter Challenge.

Author: Bunny Butler

I'm the last of the good old-fashioned steam-powered trains.

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