Travel Tales: The Hamptons

I was under the impression that you had to helicopter your way out to the Hamptons, but planes, trains and automobiles are the way to go. Whether you’re driving or biking, Route 27—known as the Montauk Highway—is the main two-lane artery stretching 100 miles east from Manhattan. One of the most important lessons I learned is that it’s important to be kind to your traffic neighbors, which means laying off the horn; it’s likely that you’ll become well acquainted with them in the thick traffic patterns. Instead of driving, I opt for the communal feeling of the Hampton Jitney or hop on the LIRR (Long Island Rail Road) for a scenic ride.

Prior to the 20th century, visitors to the Hamptons were few and far between. The “Hit the Sunrise Trail” campaign of the 1920s successfully encouraged Hamptons travel, thanks to help from the transportation efforts of the Long Island Rail Road. 

Over time, what is considered to be the Hamptons has expanded to encompass many towns including Montauk, West Hampton, South Hampton, Bridgehampton and Amagansett.

Hampton beaches contain a quality of purity and innocence. The crisp lines of the sky layered with the ocean and the silky off-white sand draw you right in. Choose from laidback public beaches, a luxury resort property or a quaint beach chalet off the beaten path.

Most of the homes found in the Hamptons are cottages or grandiose manors. My favorite houses are the dilapidated dwellings that have been restored into million dollar mansions. The best part: they retain a slightly ramshackle essence for authenticity. Almost all Hamptons quarters seem to be surrounded by green gardens—some overgrown, others perfectly manicured—but none without plush, deep green lawns as part of the landscape.

The Hamptons is known for its part-time and full-time residents. From Jerry Seinfeld, Martha Stewart and Steven Spielberg to the swank soirees taking place on P-Diddy’s yacht, a slew of Hollywood A-listers can be seen in their splendor or their moments of just being ordinary. Bump into them on a grocery shopping escapade or fighting a ticket for double parking!

Before the Hamptons became a hub to devotedly gaze into the lives of the rich and famous, it was a bohemian sanctuary for artists, including Jackson Pollack and Willem de Kooning. Writers and historians including Shelby Foote and Doris Kearns Goodwin found their peace of mind off the beaten path.

My favorite Hamptons legends are the eccentric and congenial mother-daughter duo, both known as Edie Beale. Their shabby East Hampton digs is the stage where the late relatives of Jacqueline Bouvier Kennedy Onassis exhibited their esoteric but loveable charm.

Life as a lighthouse keeper might be lonely, as portrayed in the Montauk Point Lighthouse Museum, but the first lighthouse in New York State imparts a stunning view of the coastline.

Museum lovers will also appreciate the Whaling Museum in Sag Harbor. Housed in a Greek revival mansion built in 1845, the museum displays 100-year-old genuine whale jawbones, tools and weapons of whalers, and whale oil samples.

There is something for everyone in the Hamptons, especially when it comes to food. Aside from the backyard barbeques and park clambakes, there’s a nice collection of restaurants, many of which feature fresh local seafood as the primary ingredient.