After a busy week in the office of Bernard Olcott & Associates on the 33rd floor of the Pan Am building, it was time to close up shop on Friday afternoon. It was July 1966, the pavement outside was soft from the searing heat of the sun. Summertime transforms Manhattan into a tropical sweaty island, albeit with world-class dining and entertainment options.

We strolled back to Dad’s large efficiency apartment at the Peter Cooper Hotel on 38th and Lexington, grabbed our stuff for the weekend, and took the 7 train out to Long Island City where Dad kept his car, the “horsemobile” – see image below – during the week. Like a Canada Goose in periodic migration, every weekend we plied our way east away from the hot shimmering city onto the Southern State Parkway until it emptied out on country roads. (This was before the Long Island Expressway was extended to Riverhead.) There, we followed Hot Water Road from Manorville all the way down to Route 27, making a left in Eastport. Through picturesque villages with quaint cottage-like storefronts, we wound our way past Katrina’s Deli (the logo was a haunting blond girl wearing a Viking-styled horned helmet), Go Kart tracks, and roadside ice cream parlors with high peaked roofs.

Chrsyler 300

1961 Chrysler 300G.  The “Horsemobile.”  This car was the bomb!

We had been going to Southampton every summer that I could remember. Long Island, whatever else you want to say about it, is a place of great variety. On the western end, it hosts two substantial parts of New York City and both its airports. However, once you cross the Queens-Nassau line, space seems to open up, revealing meadows of soft luscious grass, bunnies hopping and feeding gently, fireflies lifting and hovering, and streams of cooler air, even in the summer. Some people think that “Long Island” only starts past that Queens-Nassau line and are surprised to learn that the island in fact stretches from the Verrazano Narrows all the way to Montauk Point. A roommate of mine at Tufts, Roger, was one of these. He came from Brooklyn and was persuaded that there must be a “canal” (or something) separating Queens from Nassau.  There is no canal or wall, for that matter, just a municipal line.  I am sure that he would also be surprised to learn that his native Brooklyn (and all of Long Island for that matter) must have been a rabbit kingdom for thousands of years; the coney in the place name “Coney Island” is actually an archaic English word for hare.

As Dad drove the “horsemobile” that night, a Rheingold Big Mouth beer secured firmly between his legs, I asked him about the first time he came to Southampton.

It was in the 1940s, about the time he had been skiing furiously every weekend at Franconia Notch, NH. In the summer of course you need to find something else to do. Together with his girlfriend at the time – I’ll call her “Miss Sporty” – they hatched an evil plot (whenever you hatch plots, they are by definition “evil”) to bike from Queens the entire length of Long Island out to the end, Montauk Point. The equipment available at the time were of course quaint Schwinn bicycles, with a convenient basket in front and a bell on the handlebars to warn off errant pedestrians. Leaving first thing on Saturday morning and making maybe 13 miles an hour, they hoped to reach Montauk by sundown. And then the plan was to bike back the next day.

Bernard Olcott 1946

Dad with a date in the 1940s.  She is probably not the Miss Sporty in this story, but no way to tell for sure.  This girl seems to be wearing a Russian royal emblem on her dress.  A Russian soirée?

So this little sports trip was to involve an overnight, he explained. He took a swig from his Big Mouth, his face and hands faintly illuminated from the “horsemobile’s” instrument cluster.  I could see the push button transmission buttons behind him, off his left side.


Now in the 1940s, motels by the highway were far and in between. There were no Motel 6s, no “light left on” for the weary traveler (and traveling companion). Hell, there weren’t many highways. The most dependable lodging to be found in towns and villages of the époque was the ubiquitous rooming house, typically owned and operated by a matriarch who answered to “Mrs. Battle Ax.” This lady would be damned if she was going to open her doors to unmarried couples looking to fool around and turn her place of decency into a “flop house.” Especially on Saturday night!

Dad had considered this problem with his usual guile and cunning. He devised the following elegant solution: Miss Sporty accompanied him to the jewelry store the day before the trip where they ooed and awed over a few engagement rings and – wink wink – bought one taking care to keep the receipt in case the engagement fell through. They set off for Montauk early the next morning, steering their bikes into the rays of the rising sun. They must have spent a great day admiring the increasing charm of the villages and fields as they headed progressively ever eastward.

Finally, they arrived in Montauk and found a rooming house by asking around. Mrs. Battle Ax welcomed them inside. “Newly married are you?” “Yes, we biked out from New York City this morning,” gushed Dad. “Oh, you poor dears must be tired,” said Mrs. Ax, her maternal instincts flashing hot like a menopausal shock 20 years previous. Dad and Sporty signed the registry as “Mr. and Mrs. Bernard Olcott.” After a sumptuous feast of lobster and Rheingolds, giggling insanely about how they pulled a fast one over on Mrs. Ax, they retired back to the rooming house to fool around. On a Saturday night. The loudest part must have been the laughing.

Listening to Dad’s story, I looked out the window to see a parade of quaint villages passing by. Westhampton, Quiouge, Quogue, East Quogue, and so on. Each town more beautiful than the last.  No wonder he came back. I wondered aloud if all of New York State was comprised of such successions of picturesque towns on pleasant rural 2 lane highways. “No,” he said, “this was special.” After he married wife no. 2 (my Mom) in 1955, he came back to Southampton each summer, making it the family summer home.

Mom and Dad at MC

The only known picture of my Mom (Wife no. 2) and Dad together.  The Meadow Club, Southampton, 1955.  (My Grandmother Margo Alain and Albert Moakler can be seen in the background, awaiting their turn to be photographed).  Photo taken by Irving Cantor.

Through my Grandmother, he met the players in the village, among them Ivan Obolensky, who welcomed the young couple and later sponsored my Dad for a membership at the Southampton Yacht Club. My folks rented a little cottage on Meadowmere Lane, the same place that the Gould family used to rent year in and year out. He bought a pretty lot on the corner of First Neck Lane and Ox Pasture Road. But then suddenly, the marriage was over in 1962. Dad figured that he didn’t need the lot after all and sold it, clearing a couple of thousand dollars – a tidy sum in 1962. (Too bad, that same lot today would fetch millions).

First Neck Lane

The lot on First Neck Lane on a beautiful late spring day in 1961. Notice the horsemobile parked on the right, in the distance.


The same lot on a beautiful late spring day 55 years later.  The tree on the left has the same limb structure.

We pulled into the pebble driveway late that July night, the tiny stones rattling under the horsemobile’s tires. We had arrived at our Southampton home on South Main Street which circa 1966 was — surprise, surprise — an old Victorian rooming house!  The clapboard house is still there today next to the Rector’s house (it was Reverend Foster in the 1960s) at St. John’s Church; of course today it is nicely renovated.  Back then it was a quaint old Victorian farmhouse, with a welcoming porch and green shutters.  And the battle ax?  An elderly woman in an housedress named Mrs. Fordham, who smelled oddly of baby powder.   The rooms upstairs were simple and clean, two single beds with an old sink in the room.

And 35 years later, I found myself at a Victorian rooming house with my own children, for ski weekends at Hunter Mountain.  (Today we call them “Bed & Breakfasts“).  The past really does connect with the future!

Next Week: Southampton Weekends in the mid-1960s!


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