A Trip to Shelter Island, Just Outside of New York City

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Shelter Island occupies a delicate position, being less than half a mile from Long Island’s laid-back North Fork but also roughly the same distance from the South Fork — i.e., the Hamptons. The old-money families who have summered on the small island for generations, along with the 2,500 year-round residents, regard the Hamptons crowd much the way the residents of East Egg looked upon those of West Egg in “The Great Gatsby.” There is always the worry that the flashy new money will skip across the water and spoil their quiet paradise.

One summer 10 years ago or so, my wife and I stayed at the Chequit Inn, a Victorian-era hotel in Shelter Island Heights that was charmingly outdated and casual. We rented bikes and rode all over the 29-square-mile island, which is 90 miles from New York City, give or take, exploring drowsy beaches and coves, admiring the summer cottages and hitting the island’s only supermarket for sodas and snacks. Everything about the place felt chic, relaxed and timeless.

Then, this spring, I learned that the Pridwin Hotel and Cottages, the biggest hotel on Shelter Island and a mainstay since 1927, was getting a major renovation under new ownership. It followed the recent sale and overhaul of both the Chequit and the Ram’s Head Inn, another nearly 100-year-old hotel. Was glitz coming to Shelter Island?

In early June, I set off on a two-day visit to find out. I left my apartment in Brooklyn at 10 a.m., and by 12:30, I was driving my car onto the North Ferry at Greenport (the South Ferry connects the island to the South Fork).

I again booked a room at the Chequit. The hotel has been refurbished inside and out and now features an inviting patio area, a new Asian-inspired restaurant and a beachy beige color scheme instead of the old colors, dingy green and white. At $400 a night (on a Monday, no less), it was much more expensive than the funky old Chequit. But it hadn’t been turned into Nikki Beach by any stretch, and I found the same relaxed vibe. I practically checked myself into my second-floor room, which had a view down to the harbor.

Shelter Island may see itself apart from the Hamptons, but it’s a similarly wealthy enclave that caters to travelers with means. Prices were especially high, even prohibitive, in this summer of record-high inflation. I spotted a $45 lobster roll on one lunch menu and paid $7 for a bottle of water and a cookie. With half a dozen or so hotels on the island, the Chequit was the cheapest out of the three I considered.

Staying in Greenport and day tripping to Shelter Island used to be a more affordable option, but as that town has become more popular with city dwellers during the pandemic, hotels there have become nearly as expensive, averaging around $330 a night.

But one thing remained a bargain: renting a bicycle at Piccozzi’s Bike Shop, down the hill from my hotel in the village of Dering Harbor. I paid $25 for four hours and got 10 times that back in pleasure just bumming around all afternoon.

First, I cycled over to Marie Eiffel, a cafe and market in the village popular with islanders and tourists alike. I ordered a sandwich then pedaled off to find a picnic spot along the harbor.

After lunch, I rode up Harbor Lane, discovering a neighborhood of fancy houses perched on the cliffside; cycled down the island’s more rural midsection on cracked, uneven roads; and rode east to Menhadn Lane, a semi-secret beach known to locals and officially designated a town landing, not a beach. The settled parts of the island offered a certain manicured prettiness, but it was common to go around a bend or turn right at a crossroads and be in a landscape of untamed beauty. Wild rambler roses were blooming everywhere in dense foliage and I kept inhaling the fragrance of them as I rode.

Finally, I stopped into the town center, such as it is, with its municipal buildings, bank and other services, to visit a wonderful used book store, Black Cat Books. The shop, which moved from Sag Harbor 10 years ago, has a large selection of art, design and photography titles, as well as fiction and other genres, and it’s easy to spend an hour browsing.

After I returned the bike, I went back to Marie Eiffel, where I bought an ice cream sandwich and sat on the deck behind the café, watching the boats bob in the harbor. A sign posted on a fence scolded “No Cell Phone Chatter,” which made me smile, but I had the deck and view to myself anyway.

That sense of being alone on the island would happen repeatedly during my short stay. For instance, I drove out to Reel Point just before sunset. It’s reached by going over a causeway to Ram Island, a chunk of land extending off the main island into Gardiner’s Bay. At Ram Island’s southeasterly point, a thin sliver of barrier beach — Reel Point — juts into the water. The open view of sea, sand and sky was stunning, and it was just me and the piping plovers to enjoy it.

That evening, I lingered on Ram Island to have dinner at the Ram’s Head Inn, which has a new owner and a new restaurant focusing on farm-to-table dishes, but otherwise looks much the same. A 17-room country inn clad in cedar shingles, it’s situated on four and half acres overlooking the water. Adirondack chairs were lined up in the big backyard and facing west to take in 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 bath.)

In the morning, back at the Chequit, I woke to a crowing rooster and the rising sun through my window. I wanted to get an early start: I planned to hike Mashomack Nature Preserve, more than 2,000 acres of tidal creeks, oak woodlands, freshwater marshes and fields. Forty years ago, the Nature Conservancy and the residents of Shelter Island banded together and bought what had been privately owned land, keeping almost a third of the island out of the hands of developers.

Mine was the only car in the parking lot. The hikes range from as short as .2 miles to 4.4 miles, and the trails connect so you can piece together longer walks. I plotted a route that took me through forest and along the edge of a tidal creek, before opening into a vast field. Rambler roses lined parts of the trail, and a breeze kicked up their sweet, familiar scent.

Before I left the island, I swung all the way west to Sunset Beach, where 25 years ago, the hotelier André Balazs bought a dilapidated motel and restaurant and turned it into a sexy beachfront resort of the same name that draws an international party crowd, much to the old-guard’s displeasure. It marked the first sign of the arrivistes. (Rooms go from a low of $479 a night on weekdays up to $899 a night on the weekend.)

Just down the road sits the Pridwin, a big white box with a deep front yard overlooking the bay. The hotel was bought by Cape Resorts, which has a track record of taking historic properties, like Congress Hall in Cape May, N.J., and Baron’s Cove in Sag Harbor, and reviving them.

Glenn Petry, whose family has owned the Pridwin since 1961, and who has partnered with Cape Resorts, told me he felt a certain pressure from islanders to retain the look and feel of the hotel, even amid the extensive renovations (it opens to guests in July; rooms will be more than $500 a night in season).

“There’s no question that there’s change afoot on Shelter Island,” Mr. Petry said. “It’s definitely being led by the real estate market.”

Driving and biking around the island, I’d noticed freshly cleared building sites in wooded areas, soon to become new vacation homes. Perhaps because I visited during the week, or perhaps because the high season hadn’t fully begun, but Shelter Island, to me, even amid these changes, still felt drowsy and unpopulated.

I hoped to come back again in another 10 years and say the same thing.