A Romantic Beach Weekend in East Hampton
Table of Contents
Story and photos by Jeanine Consoli (unless otherwise indicated)
As a native New Yorker, I loved the energy of working and playing in Manhattan, except during the summer months. The “Dog Days of Summer,” the hottest days of the year, meant that weekends called for getting away from all that asphalt.
My favorite destination close to the city was the Hamptons. Maybe you’ve heard of them?
The Hamptons are a series of beach towns along the South Fork of Long Island, that start in the village of Westhampton, and stretch 46 miles east to “The End,” also known as Montauk.
Popular as a playground for the rich and famous, the area has been the backdrop for movies and television shows featuring the colossal beachfront mansions and the fabulous summer party scene. But, that is only a small slice of life out east.
The area’s history goes back to the early settlers who farmed and made their living off the land and the sea. The combination of the old and new, rural, and upscale beaches by day and vibrant life at night makes this an ideal location for a getaway. I chose to stay in East Hampton, but all the towns and hamlets offer things to see and do just a short drive along Montauk Highway.
East Hampton’s Historic Past
East Hampton was the first settlement in New York with the purchase of Gardiner’s Island in 1639 from the Montaukett tribe. Later, East Hampton was settled in 1648 (before New York City had its charter) by farmers and fishermen looking to make a new life. The 34 settlers, originally from different New England towns, were sold land titles by Connecticut governors who purchased the parcel from the Montauketts.
It is said that early settlers adopted the laws of the Connecticut Colony and had strict religious beliefs. Witches and witchcraft trials were prevalent hundreds of years ago, but unlike Salem, Massachusetts, its reputation changed. After the railroad was built from Long Island to Bridgehampton in 1870, it was, and still is, a refuge from city life stresses for the artistic and wealthy. Some of the oldest families can trace their lineage back from 10 to12 generations. East Hampton still has remnants of its seventeenth-century beginnings reflected in its historic windmills and the first Presbyterian Church founded in 1648. This idyllic town has so much to offer.
Getting There
The Hamptons are accessible by train, bus, or car from Manhattan. The drive is about 2-3 hours (depending on traffic). The train from New York is really convenient and leaves from Penn Station. The Montauk Branch of the Long Island Railroad has various stops in the Hamptons.
There are a few bus lines with different amenities and price points as well. Check these three companies to choose the best option for you: Hampton Jitney, Hampton Luxury Liner, and Hampton Ambassador. There are ferries from Connecticut and flights from various area airports.
Stay in a Historic Inn
The Hedges has a storied history that is over 300 years old, beginning with the arrival of William and Rose Hedges, who fled from Maidstone, England to Massachusetts and later, to East Hampton. Generations of Hedges lived on the meadowlands that were appointed to William and prospered as farmers, whalers, and cobblers. One descendant, Matthew Hedges, fought with 5,000 fellow villagers in the American Revolution. The barn at the back of the property, as well as the cellar, have a fascinating history. The cellar was once a stop on the Underground Railroad.
It wasn’t until 1873 that the house received two additional floors and became a boarding house for John Hedge’s wife Caroline to run. Her visitors were famous residents of New York and Philadelphia, who repeatedly returned for her cooking and warm hospitality. Caroline made The Hedges a treasured landmark, which is now listed in the National Register of Historic Places.
The Hedges has 13 gorgeous, renovated rooms with en-suite bathrooms and daily continental breakfast served in your room or a multi-course version downstairs in the sunny dining spaces indoors and out. Executive Chef Jenny Lilja is happy to prepare a picnic for any outing or help find a great place to eat out.
The Inn strives to meet all of your needs, including passes for the best beaches, equipment to lend, and suggestions for seeing and doing. They even provide free yoga (and equipment) on Saturdays and Sundays (weather permitting).
We chose to stay in a bed and breakfast, but there are so many unique inns and hotels. This link will give more information about other lodgings in East Hampton.
Things to Do in The Hamptons
The beaches are the biggest draw, and there are five terrific options in East Hampton. Main Beach is a public beach with lifeguards, a snack bar, and bathrooms. There is a fee to park, but you can get on any of the beaches for free if you walk or ride a bicycle. If you stay at an inn or similar lodging in the village, you may receive passes to park for the duration of your stay. Discover the other beaches – Egypt Beach, Georgica Beach, Two Mile Hollow Beach, and Wiborg Beach that require a parking pass but are stunningly beautiful. Other than Main Beach, you will have to bring snacks and drinks. There are plenty of great options in town to grab provisions to make a picnic lunch. Below are some other fun ways to enjoy more of the Hamptons.
Main Beach Expeditions offers surf camp, private surf lessons, kayak, SUP, and daily surfboard rentals.
Visit Wolffer Estate for a wine tasting on their veranda. Long Island is the only region on the East Coast to grow European vinifera grapes, and the wines produced here are outstanding. Reservations required.
- Charter a Fishing Boat. Lady Grace Charters offers full or half-day trips, including tackle and bait. They have various excursions, including a tuna and a striped bass charter.
- Learn how to sail. Sail Montauk provides private charters, lessons, and rentals. There is nothing more romantic than a sunset sail.
- Indulge your inner cowboy at Deep Hollow Ranch, the oldest working ranch in the United States.
- Montauk Downs State Park Golf Course is a public course if you want to play a round. Head to the main website and search for Montauk Downs for information on tee times and availability.
- The shops and art galleries on Main Street in East Hampton are a fun diversion. From designers to local Hamptons merchandise you can find anything you want or need.
Where to Eat in The Hamptons
There is no shortage of exceptional dining in all the villages and hamlets in the Hamptons. It depends on what you are looking for and your price point. If you have a car and want to travel, there is no better place to get a lobster roll than at two popular roadside stands, the Clam Bar or The Lobster Roll in Amagansett. Further out in Montauk, there are several dockside restaurants with views of Block Island Sound.
Gosman’s offers seafood favorites in three different spots on their famous dock – The clam bar, the Topside, or the traditional restaurant.
There are some great spots in town like Sam’s, a local pizza restaurant where locals and celebs have rubbed shoulders since 1947. If you are looking for something a little more upscale but still casual, try Cove Hollow Tavern. This East Hampton restaurant offers a lovely Mediterranean inspired menu. The limited outdoor section has a few well-placed tables and indoor seating if there is inclement weather. The food, candlelight, and warm, helpful service make this a perfect choice for a relaxing evening.
It's Time to Plan Your Perfect Visit to The Hamptons
A weekend is the perfect amount of time to feel refreshed and relaxed while enjoying some of the best experiences in East Hampton. If you stay longer, you can travel up and down Montauk Highway and enjoy more of what the Hamptons is known for. Enjoy gorgeous sand, incredible food, art, music, and maybe a sighting or two of your favorite celebrities.
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Jeanine Consoli is a freelance travel writer, photographer, and foodie based in Washington Crossing, Pennsylvania. A retired elementary school teacher, she used her summers to feed her passion for travel and kept journals of all the destinations she explored. Today, Jeanine is working as a writer full-time. She loves uncovering the history and understanding the culture of each location, including the local flavors of each unique place. She has traveled extensively in the United States and Europe and is excited to keep adding to the list, finding unique sites that are off the beaten path both at home and abroad.