As someone who has lived in the Hamptons for most of my life, I can always tell when summer is over: suddenly, it becomes incredibly easy to get around.
In July and August, I automatically have to build traffic into almost everything I do. Drives that should take 15 minutes can take considerably longer, parking becomes challenging, and there are typically long lines everywhere.
But luckily, once the fall season settles in and the Hamptons have entered their offseason, I can get in my car and go anywhere I want with ease.
Sure, the quiet comes with tradeoffs, but I wouldn’t want to be anywhere else in the colder months.
The hotels are more relaxing once the summer rush ends.
When I take a summer staycation at a hotel in the Hamptons, my schedule is packed with dinners, beach time, events, and shopping. So, if I ever want to really enjoy the local accommodations, I prefer to do so in the winter.
Once it gets colder, I can take the time to truly enjoy the property, sit by the fireplace, and have a gourmet breakfast without rushing.
Some of my favorite places to stay are the Maidstone and the Baker House 1650, both located in East Hampton. I also love Gurney’s Montauk Resort and Seawater Spa, which offers fixed-price meals at the restaurant and hosts mixology classes throughout the offseason.
It’s also much easier to go out to eat.
I don’t even attempt to dine out on summer weekends, when many of my favorite spots are packed. However, during the offseason, I love that I can check out restaurants I wouldn’t otherwise visit in the warmer months.
Even though many restaurants close down during the offseason, I love checking out places that do stay open year-round, including Bistro Été in Water Mill and Almond in Bridgehampton, both of which are among the most popular eateries in the Hamptons.
Out in Montauk Village, the Montauk Bake Shoppe is famous for its fried jelly croissants, but during the summer, it can be so busy that I rarely even attempt to get one. In the quieter months, I can stop in without delay.
There’s still plenty to do — but you need to know where to look.
There are considerably fewer events in the offseason, but that doesn’t mean nothing is happening.
Since the beaches are dramatically quieter in the fall, I love surfing in October and early November, while the water is still warm enough. Later in the season, I like to go on seal-watching hikes and cozy wine tastings.
Many establishments also host a variety of events and activities throughout the quieter months. Guild Hall continues to have films, exhibitions, talks, and performances, while Sag Harbor Cinema has screenings. The latter also hosts HarborFrost, a fun outdoor winter celebration that features hot cocoa, ice dancers, and live music.
I also enjoy going to Buckskill Winter Club for outdoor ice skating with my family and playing indoor tennis at Sportime Quogue.
The holidays are one of my favorite times to be here.
Once the Hamptons International Film Festival and Sag Harbor American Film Festival are over in the fall, the community quickly transitions into the holiday season — one of my favorite times to be here.
East Hampton, Bridgehampton, and Sag Harbor in particular are very festive. The trees lining the villages are lit, and I always look forward to seeing light displays and holiday decor throughout the community.
The hardest part about the offseason is making a living.
Because the Hamptons economy remains highly seasonal, there is considerably less work in many industries during winter.
Weather events like a snowstorm can create opportunities for people through shoveling and property management work, but it’s not really possible to build an entire year around the hope that it’ll snow.
In my case, I own an event production company, so with the area extremely quiet, I have to get a little creative.
Winter is when I do a lot of work to prepare for the summer, including client outreach, partnerships, travel, and planning.
During the offseason, I take my work with me to New York City, Miami, Palm Beach, parts of California, and increasingly, internationally.
I wouldn’t want summer in the Hamptons to last all year.
I find it fascinating how often people ask me what it’s like to live in the Hamptons year-round.
It reminds me of when I visited Block Island in Rhode Island, once in March and another time in August. It was the same place, but it almost felt like two completely different destinations. That’s how I think about the Hamptons.
Winter has its drawbacks. Farmers’ markets close, there are fewer events, some restaurants disappear until spring, and there is less work.
That being said, I don’t see the offseason as the lesser version of the Hamptons. After all, I can go to dinner spontaneously, play tennis indoors, surf in October, and have a relaxing staycation.
I’ve learned to appreciate the quiet, because in the blink of an eye, the summer crowds will be back and the busy season will start all over again.