Under New Ownership, The Ram's Head Inn Is Quietly Reimagined

A historic property famed for hosting a post WWII gathering of nuclear scientists, including father of the atomic bomb Robert Oppenheimer, The Ram’s Head Inn was owned by a local Shelter Island family for over forty years before it was sold at the peak of the COVID pandemic to a new owner, real estate investor Aandrea Carter.

It was Carter’s very much accidental visit to the inn via boat weeks earlier that was her first introduction to the scenic seaside hotel. The unplanned stop on her tour of local waters set in motion Carter’s interest in purchasing the classic 4.3 acre property perched above Coecles Harbor. 

“We’re on the boat and it’s six hours later, and we’re all feeling a little hijacked. The last stop was [The Ram’s Head Inn], but we all forgave the captain because many of us hadn’t been there before. I fell in love immediately with the property … pulling in by boat, coming into Coecles Harbor, and all of a sudden you turn the corner and there it is,” recalled Carter. “It’s a pretty stunning view from the water.”

According to Carter, who resides part-time in Sag Harbor, it was only after the “kind of quick deal” was sealed that she learned the previous owners, the Eklund family, had been trying to sell for years.

She closed on the property, she said, on March 18, 2021, and, after a whirlwind cosmetic renovation and property-wide reboot, it opened under her ownership twelve days later.  

Carter’s interest stemmed from her career turning around older properties and restoring them to their original glory. She is the president of The Carter Group, a real estate investment firm based in Kansas City, MO.

According to a biography of Carter on her company’s website, she is an investment real estate broker with “extensive experience assisting clients buying and selling multi-million dollar investment properties.

She has owned and operated over 200 investment properties, ranging from investment housing projects to commercial office buildings. She is also an expert in re-marketing under-valued property through rehabilitation.”

The Ram’s Head Inn was sold to Carter for $7.95 million dollars in 2021. She said she’s never before owned a hotel, bar, or restaurant. 

The sale was just one of several in recent years that have seen established, name-brand properties on ferry-dependent and traffic-light free Shelter Island change hands; namely, The Chequit (also sold off by the Eklund family) and The Pridwin, two of the most popular hotel destinations in town, were purchased by new owners who have re-imagined these classic properties for a new generation.

All of which is sending a pretty bright signal that Shelter Island, nowadays, is very much Hamptons-adjacent, and the influx of monied investors and second-home owners has opened the door for more marketable approaches to visitor-ship and hospitality.

For Carter, however, the potential to return the Ram’s Head Inn to its former glory, and to make it an even more inclusive hub for community events, is part and parcel of her takeover.

She said she’s well aware of Shelter Island’s exclusivity, and wants in fact to leverage it to create a worthy destination for diners, hotel guests, and also larger groups seeking privacy and beach-side comfort.

The hotel, built in 1919, is still the same traditional, wind-swept structure on a hill, a sort of grand dame on the narrow causeway that leads to Big Ram Island. Aside from the aesthetic updates – Carter said she “touched every inch” of the hotel’s 12,000 square feet – the difference has primarily been in the vision.

From re-conceptualized guest and dining experiences, to pickleball courts, to seafood boils and picnics on the lawn, to working farms on-site, the Ram’s Head Inn wants to be a multi-purpose destination that can accommodate groups big or small, and do so concurrently with other events and activities taking place across the sprawling property. 

Yet, the charm of The Ram’s Head Inn, and Shelter Island in general, has always been its ability to resist change. The smallest of the five East End towns is still very much a place where time yawns at itself.

The pace is languid, the access is limited to boats, ferries and motor-travel, and it can feel very much a world apart, spiritually-speaking, from the mainland. Carter said she wants people who “discover” the Island to keep it that way.

“I think Shelter Island is a bit of a time capsule, and it needs to be. This is a very special community and it is a destination … the ferry is a reset for people, you go from work mode to vacation mode, it gives everyone an opportunity to catch their breath.”

A big part of the allure of the Carter-owned Ram’s Head has been Executive Chef Joe Smith, a Shelter Island native who Carter said she was lucky to retain. “People think he’s a new chef because the food is so very different now,” she said. “He’s not new, he’s just been unleashed. I literally said, ‘Joe, please make what you want.”

On-site organic gardens and local farms are the sources for his menu, which Carter described as “farm-to-sea-to-table organic American cuisine.” The venue also holds weekly foodie events like a seafood boil and a picnic on the lawn.

Yet, the hotel’s most romantic draw remains its remote location-nested-in-a-remote-location, distraction-free setting. It’s what drew Oppenheimer and other scientists to a meeting of American physics giants at the hotel in what is now known as the first Shelter Island Conference, held in early June of 1947. 

“We also have those types of meetings,” said Carter. “Think-tank-type meetings where we’re not allowed to talk about who’s staying here and what they’re talking about. We are the site for that kind of activity.”

That’s also due to keeping the property open year-round, said Carter, to accommodate the inn’s place as a venue for seminal family and community events.

“People want to see these old buildings maintained,” said Carter. “Especially a historic one like this. It’s the site of so many weddings, important birthdays, memorial services. We want to be open as needed because this place is part of the family scrapbook on Shelter Island.”

The Ram’s Head Inn is located at 108 Ram Island Drive, Shelter Island. For more info, visit: theramsheadinn.com