A trip to Shelter Island, just outside New York

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Shelter Island occupies an awkward position, less than half a mile from the laid-back North Fork of Long Island, but also about the same distance from the South Fork, i.e. the Hamptons. Old fortune families who have summered on the small island for generations, as well as the 2,500 year-round residents, view the crowds of the Hamptons as the residents of East Egg watched those of West Egg in “The Great Gatsby”. There is always the fear that flashy new money will jump through the water and spoil their quiet paradise.

One summer about 10 years ago, my wife and I stayed at the Chequit Inn, a charming, old-fashioned Victorian hotel in Shelter Island Heights. We rented bikes and rode the entire 29-square-mile island, which is 90 miles from New York City, or so, exploring beaches and sleepy coves, admiring summer cottages and hitting the only supermarket in the island for sodas and snacks. Everything about this place was chic, casual and timeless.

Then, this spring, I learned that the Pridwin Hotel and Cottages, Shelter Island’s largest hotel and a mainstay since 1927, was becoming a major renovation under new ownership. It followed the recent sale and refit of the two the check and the Ram’s Head Inn, another nearly century-old hotel. Was glitz coming to Shelter Island?

At the beginning of June, I undertook a two-day visit to find out. I left my apartment in Brooklyn at 10 a.m. and by 12:30 p.m. I was driving my car on the North Ferry to Greenport (the South Ferry connects the island to the South Fork).

I rebooked a room at the Chequit. The hotel has been renovated inside and out and now features an inviting patio, a new Asian-inspired restaurant, and a beach beige color scheme instead of the old, dull green colors and white. At $400 a night (on a Monday, no less), it was way more expensive than the funky old Chequit. But he had not been transformed into Nikki Beach all the time, and I found the same relaxed atmosphere. I practically settled into my room on the second floor, which had a bird’s eye view of the harbour.

Shelter Island can be seen apart from the Hamptons, but it’s an equally affluent enclave that caters to travelers with means. Prices were particularly high, even prohibitive, in this summer of record inflation. I spotted a $45 lobster roll on a lunch menu and paid $7 for a bottle of water and a cookie. With half a dozen hotels on the island, the Chequit was the cheapest of the three I considered.

Staying in Greenport and taking a day trip to Shelter Island used to be a more affordable option, but as this town has become more popular with city dwellers during the pandemic, hotels there have become almost as expensive, with an average of around $330 a night.

But one thing was still a bargain: renting a bike from Piccozzi Bike Shop, down the hill from my hotel in the village of Dering Harbour. I paid $25 for four hours and had 10 times the fun having fun all afternoon.

First, I cycled to Mary Eiffel, a cafe and market in the village popular with islanders and tourists. I ordered a sandwich then cycled to find a picnic spot along the harbour.

After lunch, I walked up Harbor Lane, discovering a neighborhood of luxury homes perched on the cliffside; cycled the more rural middle section of the island on cracked and uneven roads; and rode east to Menhadn Way, a semi-secret beach known to locals and officially designated as a landing town, not a beach. The inhabited parts of the island offered a certain manicured beauty, but it was common to make a bend or turn right at a junction and find yourself in a landscape of rugged beauty. Wild climbing roses bloomed all over the dense foliage and I continued to breathe in the scent as I rode.

Finally, I stopped in the city center, as it is, with its municipal buildings, its bank and its other services, to visit a magnificent second-hand bookstore, black cat books. The shop, which moved from Sag Harbor 10 years ago, offers a wide selection of art, design and photography titles, as well as fiction and other genres, and it’s easy to spend an hour in browse it.

After returning the bike, I returned to Marie Eiffel’s, where I bought an ice cream sandwich and sat on the deck behind the cafe, watching the boats dance in the harbour. A sign posted on a fence admonished “No Cell Phone Chatter,” which made me smile, but I still had the deck and the view all to myself.

This feeling of being alone on the island would happen again and again during my short stay. For example, I went to Reel Point just before sunset. It is accessed via a causeway to Ram Island, a piece of land that stretches from the main island to Gardiner’s Bay. At the southeastern tip of Ram Island, a thin strip of barrier beach — coil stitch – advances in the water. The unobstructed view of the sea, sand and sky was magnificent, and only me and the piping plovers could enjoy it.

That evening, I lingered on Ram Island for dinner at Ram’s Head Inn, which has a new owner and a new restaurant focused on farm-to-table fare, but otherwise looks alike. A 17-room country inn clad in cedar shingles, it sits on four and a half acres overlooking the water. Adirondack chairs were lined up in the large backyard and faced west to watch the sunset. For the price of my dinner (salmon, a glass of pinot grigio, and dessert for $73, plus tip), I enjoyed the million dollar view. (The cheapest room at the time of my stay was $440 a night, with a shared bathroom.)

In the morning, back at Chequit, I woke up to a rooster crowing and the sun rising through my window. I wanted to start early: I had planned to hike Mashomack Nature Reserve, over 2,000 acres of tidal creeks, oak forests, freshwater marshes and fields. Forty years ago, the Nature Conservancy and the people of Shelter Island banded together and bought what was private land, keeping nearly a third of the island out of developer hands.

Mine was the only car in the parking lot. Hikes range from 0.2 miles to 4.4 miles, and the trails connect so you can piece together longer walks. I mapped out a route that took me through forest and along the edge of a tidal stream, before opening out into a wide field. Climbing roses lined parts of the path and a breeze lifted their familiar sweet scent.

Before leaving the island, I swung all the way west to The setting sun on the beach, where 25 years ago hotelier André Balazs bought a run-down motel and restaurant and turned it into a sexy resort of the same name that draws an international party crowd, much to the chagrin of the old guard. It was the first sign of the upstarts. (Rooms range from $479 a night on weekdays to $899 a night on weekends.)

Just down the road is the Pridwin, a large white box with a deep front yard overlooking the bay. The hotel was purchased by Cape Town Resortswhich has a proven track record in taking over historic properties, such as Congress Hall in Cape May, NJ, and Baron’s Cove in Sag Harborand revive them.

Glenn Petry, whose family has owned the Pridwin since 1961 and has partnered with Cape Resorts, told me he felt some pressure from the islanders to keep the hotel’s appearance, even at amid major renovations (it’s open to July guests; rooms will cost upwards of $500 a night in season).

“There is no doubt that there are changes going on on Shelter Island,” Mr Petry said. “It’s certainly led by the real estate market.”

While driving and biking around the island, I had noticed freshly cleared construction sites in wooded areas, which would soon become new vacation homes. Maybe because I visited during the week, or maybe because peak season hadn’t fully started, but Shelter Island, to me, even amidst these changes, still felt sleepy and uninhabited.

I was hoping to come back in 10 years and say the same thing.

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