2018 Dan’s Literary Prize Winner: ‘The A Train to Montauk’ by Cassandra Spiss

Long Island Rail Road LIRR train
Photo: Peter Titmuss/123RF

August in New York City has the strange and ominous feel of a coming death. The air hovers above, stagnant and heavy and the smell of overheated concrete pulses through the endless streets. The last remaining weekends of the summer are plagued by the feeling of abandonment as New Yorkers flee in droves to escape the rising temperatures. The Hamptons, Fire Island, Woodstock, anywhere but here.

If you rode the A train on any Friday afternoon like I did, you could see them clamoring into the station like little moths to a lamppost. They filled the train cars with their desperation. Straw hats peeking out through the corners of luggage teasing the rest of us like little children looking out through the backseats of minivan windows.

And finally, when the doors opened at 34th Street, like a gasp, they ran out to catch the Long Island Rail Road. The rest of us quickly darting glances to find empty seats and then heaving a sigh of relief as the train finally pulled out of Penn Station.

I watched this scene repeatedly with fascination growing up, always wondering about this place called The Hamptons and these stately people who raced off there. With each passing Friday afternoon of my childhood, it grew in mystery. The name alone, plural instead of singular, seemed intentionally vague as though it were a place so illustrious; it had to be given an alias. I had learned bits and pieces about it growing up in Brooklyn Heights.

The Heights was the kind of neighborhood where you would certainly know people who summered out East. The kids at school talked about it and at the consignment shop I worked at on Pierrepont Street; there was a woman who sold chicken pot pies she baked in Sagaponack. In the fall when her husband would bring her chocolates from Paris wrapped in pastel colored tinfoils, she would donate them to the cashiers at the shop so as to avoid the calories. I happily ate them, imagining these elegant women of the Hamptons, slim waists, gardening in silk dresses while their pies cooled on light washed marble counter tops.

While I was lucky enough to get out of town in those brutal city summers, my family never headed to the Hamptons. Aside from the fact that we were probably the least wealthy in a wealthy neighborhood, my parents just weren’t really the type. My father wore the same bright green gardening clogs for 20 years and he would scrape the mold out of jam jars to salvage the rest of it. My mother loved canned soup and she always packed sandwiches on white hamburger buns for car rides.

We spent our summers at my mom’s cottage on Rhode Island, eating clam cakes and scouring the tide pools for hermit crabs. It was the house she grew up in, her grandfather had built it with his own hands using money he’d won at an auction. We sat all day at the beach in Narragansett, scraggly haired and always a little bit sunburnt. In our tiny cabana my mother would send us down to the ocean to collect seawater so that we could boil lobsters at night. We were always the last to leave. It was simple and sweet and I loved it, but I was always curious about this place out east.

Once I graduated from college and started my first job in the city, my train rides resumed and I was reminded again about Hamptons summers. I pretended not to care as an ex-boyfriend secured a share house with some of his friends and posted photos on Facebook that I stared at over freeze pops on my Ikea sofa downtown, the heat, creaking up into the 90s, our shitty air conditioners heaving with all their might in the background.

As August approached, my roommates and I grew listless with each passing weekend until a friend came up with the suggestion that we take a hotel room in Montauk. Although the room was meant for two, she was certain all five of us could fit and, even better, the price was hard to beat.

That next Friday, instead of looking for a seat on the A train, I exited at 34th Street with the hoards of other New Yorkers, feeling a bit like a traitor, but also too preoccupied to care. As the packed train rushed from one station to the next, the feeling of excitement was overwhelming, like children on their last day of school, it was hard to remember a time when summer felt so young.

Southampton, Bridgehampton, East Hampton; the names of this secret place finally started to unravel, and by the time we arrived in Montauk I felt like I had traveled a world away from New York City. Our hotel room was, as to be expected, scratchy sheets, old carpets, quilted floral bedding, but we were elated to be here, regardless of the fact that we had been told Montauk wasn’t really considered the Hamptons.

We were instantly seduced. It was beautiful, yes, but there was an energy to it, a low hum of excitement that weaved its way through those tipsy star-covered evenings like sand sliding just through your grasp. Where Montauk had settled into her rough beauty, we discovered the Hamptons to be meticulous in her upkeep.

Perfectly hedged driveways, rows of brightly colored hydrangeas, impossibly beautiful people in long gauzy dresses dancing drunkenly in the moonlight like something you would read about in a Fitzgerald novel. We watched the sunsets nearly swallow us whole across from Gosman’s Dock, drank cheap liquor at the Memory Motel and sank our toes into white sand beaches.

Like a bad romance, I felt awkwardly out of place but still hopelessly enamored. We had discovered with little trouble what made this place so intoxicating and almost as quickly as we had left, we were already making plans to return.

Monday mornings back at my white-walled cubicle felt like coming down from a bad drug. The sound of printers spewing out inane memos and Nancy microwaving her Lean Cuisine exactly at noon, as she always did, seemed impossible next to the memory of the weekend. We needed to go back.

And so it began that the Hamptons became a place we knew. We learned where to get the best lobster roll, which beaches you could park at and how to properly order a BBC at Cyril’s. We spent the rest of that summer and many thereafter dangling our fingers out of cab windows after a long night of dancing, the sweet ocean breeze drying our perspiration.

We watched sunset after sunset at places I can’t recall, and perhaps, more likely, they no longer exist. We kissed boys whose names we would never remember at clambakes we were not invited to.

I am 35 now. We are driving out east, just nearing County Road 111. The clouds are moving overhead effortlessly and deliberately like boats navigating the sound. Soon we will be met by the Stargazer sculpture, which sits on a farm on the east side of the road. I Googled it once to learn its name and discovered that the artist had meant for it to portray the connection between Earth and Heaven.

That seemed like the perfect way to mark the shift between Central Long Island, with its fast zooming highways and 7-Elevens, to the lush, loopy roads of the Hamptons. I have been coming here for almost 10 years now.

My husband and I fell in love one summer at a share house. We bought a little home on Toppings Path and sold it. We had a baby. We discovered over the years that this place that seduced us with its beauty had more layers and depth to it, the more you loved it.

We didn’t come for the parties, or the restaurants, we weren’t invited anyway. We came and will always come back for that indescribable way that an old lover is sewn into your memories like a perfume you can never forget.

As we turn towards Butter Lane, I can see them, piling off the LIRR, luggage in hand, waving frantically to loved ones, we round the corner, and just like that, they’re gone.


“The A Train to Montauk” by Cassandra Spiss won the $7,500 Grand Prize in the 2018 Dan’s Papers Literary Prize for Nonfiction. Read all about the Gala Awards Ceremony at Guild Hall and Dan’s Literary Festival here.

2018 Dan's Papers Literary Prize for Nonfiction winner Cassandra Spiss
2018 Dan’s Papers Literary Prize for Nonfiction winner Cassandra Spiss, Photo: Barbara Lassen

Cassandra Spiss is a writer and entrepreneur. She has worked in the tech startup space and has written for several online publications. She more recently served as a Front Page Editor for Yahoo news, and prior to that helped launch a women’s finance website for Citigroup. She is a graduate of the University of Pennsylvania and lives in Brooklyn with her two young sons (one expected to arrive any day now) and husband, Lukas Spiss.

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