I first started going to Shelter Island in the late ’90s when I met my husband, Glenn. His family owned a historic, seasonal hotel there, the Pridwin. I had spent time in the Hamptons, but I had never heard of Shelter Island. So, when I met Glenn and learned that he had grown up there, in this place that sits pincered between the North Fork and South Fork of Long Island, I was completely intrigued.
The first time I visited was during the off-season, probably in April, and we stayed in the hotel before it was open for the summer. We were the only guests there and it was quite an experience – a little spooky, but very romantic. I thought the island was beautiful – like a hidden treasure. It had been there, right before my eyes, so close to Manhattan, and I hadn’t known.
Over the past 20 years or so, Shelter Island has become increasingly popular. That’s down to a combination of factors, but one of the most significant was André Balazs opening Sunset Beach [hotel and restaurant]; that popularised the island. And then, with the prices of property in the Hamptons becoming – I don’t even think astronomical is the right word – people started looking at the North Fork and the ultimate jewel, Shelter Island, as an alternative.
For many, it is still the anti-Hamptons. It’s less ostentatious and has a more New England feel. You can only reach it by ferry, too, and that is prized by the inhabitants, as it keeps the island quieter and less crowded. Having that little extra step to get there has saved the island from overdevelopment and has allowed it to keep its identity.
I love the topography of Shelter. It’s amoeba shaped, and if you’re on a bike you don’t have to go far – like five, 10 minutes – until you hit the water, no matter where you are on the island. There’s so much beachfront and the water is just the perfect temperature.
A third of the island is a nature preserve called Mashomack, which is really special; and there’s another large portion of the island that’s part of another land trust, called Sylvester Manor. The Sylvesters were the first European settlers on the island (the island was home to the indigenous Manhansett people for millennia). It was one of the largest slave-holding plantations north of Virginia, and it is now a pioneering educational farm wherethey practice sustainable farming and interweave lessons about its history with art programming, and music concerts. Having that connection to history, culture and the land makes the place really dynamic and unique.
When I am in Shelter Island, I feel like I have travelled back in time. There’s this kind of innocence and optimism. And it’s friendly and safe – such a contrast from Manhattan.
So, it’s not surprising that people come and visit from all over the world. They can still stay at the Pridwin, which Glenn’s family owned and ran for many, many years. We recently partnered with Cape Resorts, who did a transformative renovation of the property, adding some cottages, enlarging rooms, updating the entire facility. It’s truly gorgeous and a wonderful place for us. We have a house nearby, but we love to entertain at the Pridwin. It’s our home away from home.
The island is a great place to visit; wonderful if you’re a couple and brilliant for families with kids. There’s so much do on the island. You can go to the beach, of course, or if you like to be more physically active, cycling is very popular, and there are tennis courts and two golf courses – one public and one private.
There is also boating, all sorts of boating. In addition to sailing and motor boating, many of us enjoy kayaking and paddle boarding. There are so many inlets and connective waterways. And on land, if you are on a bicycle, you can get everywhere. I love to ride my bike, almost as much as I love to drive “Big Red”, my 1970 Buick Electra convertible.
You can find out about the Pridwin Hotel and Cottages at caperesorts.com; and see what’s on at the Stephen Friedman Gallery at stephenfriedman.com
