Not everybody wants to rule the world; I would settle for the mere mastery of time and space. And when Tears for Fears plays on the radio, I can almost achieve such feats, as the memories of Shelter Island in the summer of 2015 come flooding back, and with them a sensory overload that reverses the catalyst of the olfactory’s ability to trigger the mind; I can smell the vegetative stagnation of the July heat and refreshing salt of Gardiner’s Bay in the sparing breeze. While the rest of Long Island came to a standstill in the blazing sun and tourist traffic, Shelter Island gleamed across the water as a beacon: isolated, reticent, nostalgic, and often five degrees cooler; the perfect place to settle the morose persona one takes on during the peak season of the Hamptons.
On Tuesday afternoons, I’d load up my little four-cylinder Honda with my aunt’s collection of ’80s compilation CDs, my Kelpie companion Delilah, my best friend John, his mother Carol, and a case of domestic beer; shortly thereafter navigating the crowded streets of Sag Harbor en route to the ferry slip in North Haven. “Two passengers, round trip, please,” I’d regretfully request aboard the South Ferry — a fleet of small but stout vessels sporting four lanes for vehicles: one on the port side, three on the starboard, separated by the bridge with a passenger cabin beneath it. Though adorned with “No Smoking” signs, Carol would pull a Seneca from her blue pack and flick the flint as John and I anticipated our brief stint of “getting out of Dodge” for the evening.
As the gate opened, I’d turn the ignition and release the parking brake, grinning from ear to ear as we darted off the ferry, fresh air flowing through the moon-roof as John suggested we “wave hi to Billy,” passing the former residence of Billy Joel where we had done a landscaping job a few years prior. There was no time to stop and reminisce about mulching, we were bee-lining for the Whale’s Tale, a small joint packed with fun for the local kids, featuring an 18 hole mini-golf course, arcade, and ice cream parlor. If we were particularly hungry, we’d split an appetizer from the snack bar, but most trips we’d hold off for a parking lot beer on our way out. I’d usually insist on stopping to admire a polished motorcycle with a sidecar, before advancing on our usual route to the North; what it must feel like to cruise the winding back roads on such a machine!
Splitting the island up the middle, we headed to Dering Harbor, the least populated village in the State of New York, with 11 residents recorded in the 2010 Census. The sparse numbers are nothing new, as the village’s inception initiated with ten signatures of its incorporators: seven men and three property owning women, in September of 1916, though it would be another year before New York granted women the right to vote on municipal matters, and four years before the 19th Amendment was ratified. Early officials were tasked with converting houses that had been supplemental and thus dependent on the Manhaset House Hotel — which had burned down due to a lightning strike — into an independent village. Today it sits nestled between the boat yards that dot the coast of Shelter Island, a name which too has roots tied to the Manhaset tribe, stemming from the translation of its native title Manhansack-aha-quash-awamock, meaning “island sheltered by islands.”
From Dering we would continue to the East, through the Gardiner’s Bay Country Club, riding the hills and hugging the curves of shaded roads that reminded me of my childhood in rural Connecticut, stopping at every beach along the way to explore the shoreline and crack another can. Every now and then we’d take to the water to cool off, laughing like children baptized in the golden light reflecting off the bay. One such spot yielded a view of the Bug Lighthouse between the reeds, its lamp previously known to me only from the sands of Cedar Point County Park. We couldn’t afford much time at any location, however; there was more to see, and a ritual to fulfill at Ram Island.
Getting to Ram Island requires one to drive this marvelous narrow strip of beach bordered by rocks and osprey towers, where the sand clings to everything: socks, shoes, floorboards, frizzled hair, and worn out tires. We frequently pulled off to admire the weathered stretch of pavement that connected the rest of Shelter Island to this little slice of secluded paradise, boasting the gorgeous Ram’s Head Inn on a luscious grassy hill that fetches $300-$400 per room per night. On the Southwest corner, at Reel Point, I’d usually surrender the keys and admit to the onset of inebriation, where Carol would chuckle as she shook her head and gripped the steering wheel. We elected to polish off a majority of the blue cans rattling around the back seat, and bid farewell to the view of our own East Hampton on the horizon. It was surreal to see all that we had escaped, where the roads were backed up for miles, towel space on the beaches were fought over, and prying eyes never would have allowed such a public display. After skimming rocks and bantering for a while, and giving Delilah some much deserved exercise and sniffing time, we cleaned up the cans and cranked up Mr. Mister as we pulled away.
From here Carol would return West, via the Southern route that we may continue circling the island clockwise, in search of various suitable locations to witness the melancholic sunset which marked the passing of another afternoon of our weekly “staycation.” By now, as the alcohol was coursing through our veins, we divulged our deepest sentiments, met with motherly advice, a barrage of curse words, and carefully seeded dirty jokes to break up the mood; Carol was the perfect host. She doled out harsh realities whether they were sought or not, and uplifted spirits with off-color remarks when she knew a change in pace was required. Her gravely voice walked a razor-thin line between “oh, honey” and “hey, f*ck-o,” depending on the situation at hand. All the while she positioned us closer to the glorious splendor of painted scenery. We were a small dysfunctional family.
Kissing Rock was one of our usual sunset spots: a boulder down a steep dead-end street just beyond Quinipet Camp & Retreat Center, which was painted with an American flag tribute for 9/11, partially submerged on its Western side. Delilah would suss out critters in the tide line and crunch on the occasional shell, as Carol remarked “oh, its beautiful, honey… Very nice.” We would often bounce back and forth from there to West Neck Point, a dusty peninsula with a view of Noyac, making jokes about Belvedere Avenue and our affinity for vodka along the way, making a customary stop at one of the dead ends along Peconic Avenue.
Silver Beach was another favorite; a place of remarkable beauty, littered with tiny sailboats and kayaks, and endless rows of seaside goldenrod, bustling with bumble bees and butterflies. The sun would fall so peacefully over the vacated picnic tables as the last beach-goer shook off the remnants of salt and sand and disappeared. It always felt like we were alone here, like solitary survivors inheriting the Earth’s grandeur.
On the evenings we had a little extra jingle in our pockets, we’d seek closure at Crescent Beach, at a bar and restaurant aptly named Sunset Beach. A luxurious spot for cocktails, the restaurant featured multilevel bars, ping pong tables, and fire pits in the back. On one lucky occasion we witnessed the pressure tests of a firefighting boat with water canons affixed to the bow. Being a week night, empty seats haunted the lower portion of the venue. Nevertheless, with John’s cousin Russell in tow for one particular endeavor, we enjoyed a rare indulgence of top shelf liquor in our polo shirts, pretending to be the tourists we usually detested.
Once the orange hues had sunk below the horizon, we would invariably retreat to the Dory, a local staple which boasted appreciation for blue-collar workers on the island. It was full of our favorites: deep fried appetizers, hand crafted burgers, local seafood to die for, and open pool tables. Above the entrance, illuminated by neon signs, perched the bow of a dory, paying homage to the whaling and fishing history of Eastern Long Island. We signed on to an “industry night” discount program, still in the trial phase, aimed at the working class who catered to the weekend crowd. The beer and well prices were tantalizing, and we made sure to buy Carol dinner as payment for playing chauffeur and shrink, the leftovers of which I saved for Delilah, who lay patiently in the backseat of the Civic across the street, sprawled out in the cool night air.
Running the show was Jack, a rather cumbersome man in suspenders, who spent the greater part of each night puffing on a fat cigar just beyond the front door, greeting patrons and watching the main drag that ran through Shelter Island Heights. He was a pleasant, personable man; on our first encounter we thought he was just another customer. But he was indistinguishable from the Dory itself; this was his pride, and he paid attention to every detail. Some days he stood behind the bar, some days he discussed business in the quiet dining room, and some days he tended the stool, catching the opine of his crowd. We shared gratitude for the food and service, and discussed politics and photography with one of his bartenders: a young woman on a work visa from Bulgaria. She often greeted us with a smile, and invited us back as we packed our styrofoam containers and stumbled to the door after Carol would remind us “oh, honey, I need to get back to Aunt Ivy.”
I confess that when I first started reflecting on this brief era in our lives, I couldn’t recall what brought it to an end. Thumbing through photographs and listening to old songs had inspired me to put it into words, and the deeper I dug, the more the harsh reality dawned on me. On our last night together at the Dory, as we were nearing our usual departure time, Carol’s phone rang. She hung her head low and shook it back and forth, “oh no, oh no, oh no.” She was shocked yet somber, and refused to lift her body from the counter for several minutes. John and I already knew the cold truth: Aunt Ivy had passed away, and with her left the roof over Carol’s head — the remnants of our stability; the world changed in an instant.
We shared one last ferry ride home together, spending the following week stowing Carol’s life in boxes, sifting through rooms packed with decades worth of thrifty belongings in the scorching heat. With nowhere to stay in the Hamptons on a working-class salary and such short notice, we moved into a tent at Cedar Point County Park, where at sunset we could look across the water and see Reel Point from another perspective; Shelter Island was now nothing more than a dream, frozen in time.
As fate would have it, Carol too would pass away five months later, cementing our adventures as the last summer we would all share as our little dysfunctional family. The ’80s music would forever change, to remind me of those brief weeks rather than the decade they originated from. While I’ve traveled back to the island since, it has never been the same, but with the right mixture of photographs, playlists, and domestic beer, I can briefly master time and space; closing my eyes and breathing in that salty air, as the wind blows across my face to the ticking of that four-cylinder engine. Once again, for just a moment, I’m as free as I was in those days.