Sixty-Something: Will I See You in September?

Some people who adore summer always wish that August in the Hamptons could go on forever. They love the good weather, the fun, the galas, the parties, dining outdoors, and of course, going to the beaches. Yet there are only 31 days in August and when they are up, many have kids that are going back to school or college, while rental home folks head back to their primary homes and their careers.

There is always the feeling of things one must do before summer ends. Places to visit, whether they be beaches, restaurants, Shelter Island, Block Island, across the canal in either direction. For too many, summer ends on Labor Day weekend.

The annual September surprise in the Hamptons is that, technically, summer doesn’t end until September 22nd, and September summer days have a unique quality all their own. The wild cards for this time of year are the rental homeowners who finally get to use their Hamptons homes. You see them joyfully experiencing The East End lifestyle they wisely invested in.

The Tuesday after Labor Day is called “Tumbleweed Tuesday”  because of the quietness after the huge volume of summer folks leave. Also, Tumbleweed Tuesday is, in fact, the beginning of rental homeowners’ season. Why? Because, usually on Labor Day, there is a long line of vehicles loaded up with bicycles, surfboards, and roof racks heading West on Route 27 as the summer rental and second homeowners head back to their full-time lives. Yet on that same day, there are cars coming east with folks who owned the rental homes and now are on their trek to enjoy them. They are coming out East to repossess their dream homes and enjoy their investments while perhaps spending some of that rental money they pocketed.

A great warm, sunny day on the east end of Long Island is always enjoyable, whether it be in June or early October. Sometimes the feeling of overcrowding can ruin that wonderful feeling at a Hamptons beach or park. That’s just not the case in September.  It’s such a relaxed, down-four-notches atmosphere you sometimes feel like it’s the Virgin Islands off-season.

Finding parking spots in all the villages post-Labor Day right in front of where you want to go is always pleasant. Food shopping becomes quicker, easier, and more friendly as there are no long lines of impatient “type A” folks on the cash register line. 

Yet as the saying goes, “There are always a few weather days of the previous and next month in every month.” In September, sweatshirts, fleeces, and light sweaters come out of storage. I always remember that first day I start wearing long pants daily again. It’s hard for me to say goodbye to my favorite go-to summer shorts! Same thing with the sandals. How about the day you must start wearing socks, not because you are wearing a suit but because it’s cold? Those days usually don’t start until late October.

There is always the human element. Such as watching longtime friends head west until next year. People you see every summer. Ones whose company you enjoy and will miss. Folks you sail with or go to the beach with. People you will miss. 

In closing, I must share my favorite bizarre, upscale end-of-the-summer rental home story. A few years back, pre-covid, a South-of-the-Highway Hamptons ultra-luxury rental made the news when after Labor Day, the actual homeowners were less than thrilled when discovering the summer occupants installed a highest quality basketball half court on their driveway without permission. There was a lawsuit to have it removed. The rental folks just couldn’t understand the outrage saying the basketball court increased the property’s value. The basketball court was removed.

Slowly but surely, the large yachts that fill Sag Harbor’s docks will leave for Portofino and Palm Beach. The folks who sail late into the fall will not notice any change until the sun sets earlier and earlier. For many boaters like me, we don’t spend our time in the Hamptons but in Gardiner’s Bay. Will I be seeing you in September?