Site Loader
Second House Montauk

On the Montauk HIghway, across from the condos sits the Second House. The oldest structure in Montauk, Long Island. We visited the house whilst staying in the Hamptons back in the summer of 2010.

Montauk sits at the tip of Long Island in the area most commonly known as the Hamptons. The area is now known for its beautiful beaches and celebrity sightings, Montauk originally belonged to the Indian Algonquian tribe when European settlers arrived in the 1600s. (read more about the Montauk history.)

Second house was built in 1746, at a time when Montauk was used primarily as grazing pastures and 30 years before the signing of the declaration of independence.

After the Indians, came the shepherds. In the year 1701, four white shepherds tended the large number of cattle, sheep and horses belonging to East Hampton and neighboring towns. First, Second and Third Houses were built on Montauk for the use of these shepherds, who were called Keepers.

“Second House: the House with the Interesting Story”
Excerpt from article by Mrs. James Tyson (Caroline Kennedy) 1930 “Montauk Light” (borrowed from Montauk Historical Society.)

Second house is named simply because it was the second house to be built on the plot.

The house now stands as a museum open to visitors showing the house as it would have been furnished back in the day.

What you see is a charming small house, furnished comfortably but simply. A place that looks charming in the sunshine but no doubt would have been cold in the winters as the wind whipped across the fields from the sea.

Most visitors to Montauk would drive straight past this little house and not realise it is here. Even on TripAdvisor, Second House only ranks #21 of 42 things to do in Montauk! Other historic visits include Montauk Point Lighthouse, and the Deep Hollow Ranch, which is the oldest cattle ranch in the United States.

The History of Montauk

Montauk is a hamlet located on the eastern tip of Long Island, New York. It has a rich and varied history, dating back to the arrival of the Montaukett tribe in the 17th century. The area was later settled by European colonists, who established a thriving fishing and whaling industry in the 18th and 19th centuries. During World War II, the town became a strategic military base, and the Montauk Air Force Station was established. Today, Montauk is a popular tourist destination known for its beautiful beaches, outdoor recreation opportunities, and charming small-town atmosphere.

Despite its popularity, Montauk has managed to maintain a laid-back and unpretentious vibe that sets it apart from other upscale beach towns. Whether you’re looking to relax on the beach, explore the great outdoors, or indulge in some local seafood, Montauk has something for everyone.


I am Jay, the founder of Wine, Travel and Song. UK based, I set this blog up in 2016 to share my passion for food & drink, travel and music - Wine, Travel & Song. In these posts I share some of my passions in the hope that it may inspire you to go there, eat that or listen to this. In return I hope you will comment and share recommendations of where to go, what to eat and what to listen to!