Sixty-Something: The Hamptons’ Transformation from August to September

Years back the saying used to be that September in the Hamptons was the best kept secret. Then slowly but surely that secret was out. September is the month that the folks who are the nuts and bolts of the Hamptons really get to enjoy all the east end has to offer, without the rudeness huge crowds can create.

Beach parking is no longer a problem, even on the warmest and sunniest of weekend days. Choice seats at favorite restaurants are available without a wait. Parking in the town lots and even on the streets is easily available. The only negative is the rush hour traffic to and from the east end that still happens in the morning and the evening. After all, people still go to work daily in September.

In the next few weeks many stories will be posted about “Tumbleweed Tuesday,” that being the name locals have given the Tuesday after Labor Day. The change of the seasonal rental and vacation folks exiting the east end is that drastic.

When the bar/restaurant Nichols was in its heyday on the north side of Route 27 in Wainscott, a crowd would gather at the outside seating and just enjoy a cocktail while they watched the mass exodus of cars heading west with bicycles and beach chairs strapped to the roof or rear of the car. The local patrons, many loyal Sag Harbor golfers, would watch, sip their drinks and just smile for hours.

Folks who live in Montauk will now be able to park and shop at the local IGA with ease after Labor Day. That will be true all over the east end. Gone will the long lines due to people buying $700 worth of groceries then intensely checking the bill.

However, then there is the return of the rental home owners to do their post season victory lap as they move back into their rental second homes. It’s time for them to enjoy their summer vacation in September in the Hamptons. You can overhear them conversing with fellow second home owners who rent out the homes about how much revenue they received, could have ascertained or turned down. They compare damages done to the house and changes they will attempt to make in the off season.

September 2022 is going to be a pivotal time on the east end. With the Covid pandemic phenomenon now in retreat how will the east end respond? Will inflation continue to financially tag the local hourly wage earners? Will home values continue to rise, or stabilize or even get soft? One truly doesn’t know, but one thing folks sixty-something in age know is that rarely does living life anywhere get less expensive over time.

Back as a child I used to really enjoy an ice-cold coca cola in those special coke bottles out of the vending machines for ten cents. You put that shinny little dime in that coke machine and out with that certain noise came the very cold coke bottle. The vending machine had the bottle opener right next to where to put the dime in. Then we were told about a sugar shortage and the drink price went up to twenty-five cents and has kept on going up, no matter what the sugar market is.

Now that September is right around the corner that doesn’t mean the busy days before Labor Day wind down. Actually it is quite the opposite. The bigger private jets and helicopters are now arriving at the airports. Also, the more expensive and exotic cars seem to be appearing on the town roads.
You can’t help but notice all the lights seem to be on at the largest south of the highway homes late into the night along with huge private lawn parties.

I have a sailing ritual every Sunday night before Labor Day. I have a friend named Andrew who comes out to sail with me. We sail and if it is warm enough take a sunset swim at Sammy’s beach. Then, when it gets dark we slowly motor across Three-Mile-Harbor. While cruising we observe all the lights on in all the rooms. It is the one night all of the homes are lit up.

The lit up homes along the shore line create a Christmas eve effect. Then the following Tuesday night, all around the harbor at least three quarter of those homes are dark. They stay dark every evening until the next Memorial Day.