Southampton, NY – April 2018

The Hamptons seem mystical to me.  I have visions of the wealthy shopping in pristine villages and frolicking on diamond studded beaches closed to everyone but them.  I think of parties, decades of parties, the Great Gatsby.  I’ve been almost afraid to go there, keeping the Hamptons and their mystique at a distance.

That changed one summer, when my boyfriend decided to run the Southampton half-marathon, and wanted me to come along and cheer him on.  It meant getting up at 3 a.m. to get ready in time to board the Hampton Jitney on 4nd street in Manhattan for the two hour ride that would get us to the start of the race on time.  So I did it, sleeping on the bus, at least until dawn broke and you could see more outside the bus window.  I am always fascinated by how the scenery changes from dingy city buildings, to cramped suburban duplexes, to breezy, beachy villages as one travels east through Long Island.

We got off the bus at Southampton and walked to the middle school, where he picked up his race number and positioned himself at the starting line.  I blew him a kiss good-bye as he started off to run the 12 mile course.  Then I had another two and a half hour wait.  To pass the time, I head off by myself to find access to the beach somewhere.  I always imagined secluded, private beaches one could only gaze at from a distance, if at all.  However, maybe as we were near the downtown of Southampton or near the middle school and in a public area, I found it quite easy to head straight down the runner’s path (after the runners of course!) and turn down Old Town Road which led straight to a public entrance to the beach, not more than a 30-40 minute walk away.


Beach in Southampton, NY

The view in the morning light was magnificent.  There I was, taking off my sneakers and sinking my toes deep into the soft sand, as I strode down to the shore.  The large expanse of clean, powdering sand was marked only by the treads of beach vehicles that had rampaged in the dawn.


I had the beach to myself, save a few residents walking their dogs along the surf that morning.  Behind me the grassy dunes were dotted with multi-million dollar beachfront properties.


I strolled along the surf, gazing out into the ocean, letting the foamy waves roll over my feet as I walked.


It was peaceful, but I could not help feeling I was trespassing somehow – it was all so secluded and felt private.  I decided to turn around and head back to the point of my entrance, and not tarry on the beach too long.  A group of neighbors walking their dogs together that morning were alongside me as I exited.  They got into their black BMW SUVs, shouting good cheer to each other before they drove off.

I put my sneakers back on, and walked to the finish line, where after another 40 minutes or so I finally spotted my honey ending the race, panting and sweating.  His face was etched in pain, until he saw me cheering him on and then a big grin spread across it as he crossed the finish line.

Now it was time to explore Southampton together, at least the downtown area.  Food was our destination.  As we walk down to Main Street, I noticed several signs that pointed to how historic Southampton is – it’s the first settlement in New York, settled in 1640, the oldest English colony in the State of New York.  I tried to imagine what the town must have been like when settlers first lived there, going about their lives in cottages and perhaps going to the shore to harvest oysters?


When we reached downtown, I forgot all that quickly as we walked down pristine and tree-lined Main Street, with black and white shuttered small designer shops.  Surprisingly, not too many cafes or restaurants in the immediate area.  We decided to have brunch at 75 Main (75 Main Street, Southampton, (631) 283-7575,, where I enjoyed a delicious filet mignon beef hash with a poached egg.  The restaurant was swarming with runners that day, and the frenzied servers ran about getting all the orders in.  The patio doors were wide open, and the warm summer breezes wafted in.  It was the perfect place to have brunch on such a lovely day.

Afterwards, we walked through the area, eager to do some rich mansion “window-shopping”, but that was not to be the case.  Most lots we walked past were lined with greenery stretching it seemed half a mile high, with locked gates and security cameras visible.  There was no way to see past all of it to the houses tucked away inside the properties.  However, any residents we happened to walk by were very friendly, waving to us and wishing us a good day; we may as well have been from down the road, they were so welcoming.  Perhaps, some day!

On the bus ride home, I mused about how I felt – even though I’d only had glimpses of the life there, the glimpses shone bright.  Secluded, yet welcoming, the Hamptons still seem out of reach and distant, yet in an American way, they tell you – this is possible.  It beckons to be explored more.

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