The ‘citiots’ are coming.
Having spotted a herd of fanny packs on the horizon, I sent a fistful of golden chocolate doubloons raining down on the throng of incoming tourists. Beside me, my classmate, Dory—named, ironically enough, after the fishing boat—bellowed “Ahoy, matey!” in a quasi-pirate accent. Adjusting the feathers on my skull-and-crossbones cap, I surveyed the incoming wave of urbanites—families who, having wormed their way out of the Big Apple, now zigzagged through my sleepy, one-traffic-light-town.
Mustering up an “argh,” I rifled through the treasure chest behind me before stepping forward into the heart of the Maritime Festival to distribute my beaded necklace bounty. In the air, the briny aroma of freshly shucked littleneck clams was spread by the harbor breeze, while farther down the street North Fork chefs wielded ladles in hopes of ousting the reigning “Chowder King” from his throne. Beyond the shoreline, Greenport Harbor was dotted with every boat imaginable—from snapper-strewn dinghies to 100-foot yachts boasting oversalted names like Nauti-Buoy and The Codfather.
From the corner of First and South, a musician crooned Billy Joel’s “The Downeaster Alexa”—“There ain’t no island left for islanders like me…”—in hopes that her siren’s song would lure the beloved Long Islander’s boat back into harbor. Trailing the melody, I found myself face-to-face with a sign that read “Bootleg Alley.” All at once, I was transported back in time to the lawless, booze-infused days of the Roaring 20s—to Prohibition Greenport.
In 1854, a twelve-year-old Portuguese cabin boy named Manuel Claudio embarked on a 2,335-mile journey from Portugal’s Azores Islands to Greenport Harbor on the whaling vessel, Neva. After docking, Manuel spent the next sixteen years of his life setting sail from Greenport. In 1870, Manuel finally decided to anchor himself permanently in the seafaring village, opening a namesake dockside tavern at the end of Main Street, Greenport.
By the 1920s, Claudio’s—at this point run by Frank Claudio, Manuel’s nephew from Portugal—had transformed the sleepy village of Greenport into a booming smuggler’s cove. An upscale ground-floor restaurant, top-floor speakeasy, and underground bootlegger’s beacon, Claudio’s proudly spent the Prohibition years at mayhem’s helm. Sitting on stilts over Greenport Harbor, Claudio’s is now infamous among locals for its twelve-year history of ushering in moonlight bootleggers who, after dodging law enforcement, would slip their schooners under the waterfront restaurant. The contraband—hoisted through a trap door, which still exists behind the bar—was then routinely transferred via dumbwaiter to top-floor speakeasy patrons. During raids, patrons sent their “water glasses” down and out of sight on the dumbwaiter. Local rum running ran so rampant, in fact, that the federal government established a U.S. Coast Guard base in Greenport in an attempt to keep the town’s illicit activity at bay. Nonetheless, Greenport preserved its status as a leading stop on the booze run from the Caribbean to New York City, and is even rumored by Claudio’s current proprietor, Bill Claudio Jr., to have once been graced by the notorious gangster Bugsy Siegel. When the termination of Prohibition in 1933 finally brought an end to the $40 million bootlegging industry, Greenport Village was left in—and with—good spirits.
Leaving Bootleg Alley, I found myself scouring the doubloon-littered pavement for stray bottle caps, which glinted in the September sunlight. Nowadays, a different breed of rapscallion wreaks havoc on the village streets. Midnight often finds the village drunk reeling through Bootleg Alley to the soundtrack of clanging bottles pilfered from restaurant dumpsters—keeping anti-Prohibition spirits afloat, one might say. Though Greenport may now attract more seagulls than Siegels, its crooked past lives on.
Following Front Street back to the center of the Maritime Festival, I surveyed the sea of costumed locals around me—the bearded pirates and iridescent mermaids and squirming baby flounders. Soon, I found my gaze drifting toward the smorgasbord of restaurants that pay homage to Greenport’s seafaring history. Boasting a miscellany of nautical names, these local hubs include Scrimshaw, The Harbourfront, Crabby Jerry’s, The Clam Bar, Deep Water Bar and Grille, and—of course—the locals’ late-night favorite, The Frisky Oyster.
And yet, by moonlight boozy crowds always flock back to Claudio’s—suspended over the infamous rum running mooring grounds of decades past while swaying to “Sweet Caroline.” Good times never felt so good—(“so good, so good”)! Beyond the pier, adjacent to the parking lot, a roundabout hides in the shadows. When a gibbous moon peeks through a curtain of clouds, one can just make out the asphalt’s faded strokes of turquoise. Bathed in moonlight on the village road, there is none other than a helm.