Sixty-Something: The One Night Every Hamptons Home Is Glowing

The Hamptons consist of many small hamlets each with a unique characteristic all its own. Many of the homes are diverse in their styles from historical to ultra-modern in design. Some are small one floor cottages, others are multi-million dollar expressions of enormous wealth. However, there is one night when all of them glow, when everybody is home and in many cases having a party. It’s not Christmas and it’s not New Year’s Eve; it is the Sunday night before Labor Day.

Before living up-island I lived in the Springs, in East Hampton Village and finally in Montauk. I fondly remember noting the jovial atmosphere of the Sunday night before Labor Day. It’s like a graduation night for the whole community. The next day some folks will be boarding private jets, Jitney buses, LIRR trains, Ubers and their own family cars for the ride from summer vacation homes back to their other existence. The locals, on the other hand, are celebrating the end of their time of experiencing what they consider that yearly invasion of “Citidiots” all over their sleepy historic communities. They even have an expression for the day after Labor Day. They refer to it as “Tumbleweed Tuesday!”

There are even a few venues serving beverages on Route 27 where the locals sit and watch the “Labor Day Car Parade,” of vehicles loaded with bikes, suitcases, surfboards, kayaks, and beach chairs along with 4-5 people heading west leaving the Hamptons until next year’s summer season.

But on the Sunday night before Labor Day, there are BBQs, family get-togethers, final walks to the beaches for campfires and yes folks in their rooms packing suitcases, too.

I have a tradition of making it a point to sunset sail in Gardiner’s Bay on that Sunday evening before Labor Day. This year it was a magnificent September 1st evening with a pleasant breeze with a hint of the fall in its coolness. My sailing season stretches from May until November but there is no sight from the Gardiner’s Bay like this particular Sunday night because every home is lit up with the lights on in every room all along the shores of the Bay. Most nights perhaps one out of five homes are occupied. Even weekends in July it’s three out of five, but on the Sunday before Labor Day it seems like all are lit up. Even from way out in Gardiner’s Bay, if the wind is blowing the right way you can hear music playing, dogs barking, and children’s voices from the beaches lining the shore just after sunset. All summer long there are fires on the beach usually with folks huddled around them taking in the sky, the stars, the view, the air along with the magic of a crackling fire’s flames. On the Sunday before Labor Day there just are so many more.

It is really like the whole Hamptons community is graduating from the summer season of 2019 and saying celebrating in unison.

Now the second-home owners who rent their homes all summer long will be occupying the Hamptons and in many cases annoying the locals even more then the summer visitors. Starting now, however, with the still warm weather of September into October, parking will be easier in Sag Harbor, Southampton Village, East Hampton Village, Montauk, Westhampton and Hampton Bays. The town beach parking lots will not be filled with cars. The roads won’t have lost drivers either speeding or going too slow, and reservations will no longer be needed at restaurants. On the back roads only one of five homes will be lived in full-time and in certain sections mansions will be deserted.

However, on the one Sunday night before Labor Day all over the Hamptons every light in almost every room of almost every home seemed to be on.