Shelter Island feels chic, relaxed and timeless

Shelter Island occupies a delicate position, less than half a mile from Long Island’s laid-back North Fork, but also about the same distance from the South Fork, ie the Hamptons. The old money families who have spent generations on the small island, along with the 2,500 year-round residents, view the Hamptons crowd much as the residents of East Egg viewed those of West Egg in “The Great Gatsby.” There is always the worry that the flashy new money will jump over the water and spoil their quiet paradise.

A summer or ten years ago, my wife and I stayed at the Chequit Inn, a Victorian-era hotel in Shelter Island Heights that was charmingly outdated and casual.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 the 18-square-mile island, which is 90 miles from New York City, give or take, exploring sleepy beaches and coves, admiring the summer cottages, and visiting the island’s only grocery store for soft drinks and snacks. Everything about the place felt chic, relaxed and timeless.

Then, this spring, I learned that the Pridwin Hotel and Cottages, the largest hotel on Shelter Island and a mainstay since 1927, was a a major renovation under new owner. It followed the recent sale and overhaul of both the check and the Ram’s Head Inn, another nearly 100 year old hotel. Did glitter come to Shelter Island?

In early June I left for a two day visit to find out. I left my Brooklyn apartment at 10:00 AM and at 12:30 PM I drove my car to the North Ferry in Greenport (the South Ferry connects the island to the South Fork).

I booked another room at the Chequit. Renovated inside and out, the hotel now features an inviting patio, a new Asian-inspired restaurant and a beachy beige color scheme instead of the old 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 changed in Nikki Beach anyway, and I found the same relaxed atmosphere. I practically checked myself into my second floor room, which had a view of the harbor.

Shelter Island may see itself apart from the Hamptons, but it’s an equally wealthy enclave catering to travelers of the means. Prices were particularly high, even unaffordable, in this summer of record high inflation. I saw a $45 lobster roll on a lunch menu and paid $7 for a bottle of water and a cookie. With about six hotels on the island, the Chequit was the cheapest of the three I considered.

In the past, staying in Greenport and a day trip to Shelter Island used to be a more affordable option, but as that city becomes more popular with city dwellers during the pandemic, hotels there have become nearly as expensive, averaging around $330 per night.

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

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

After lunch I drove up Harbor Lane and discovered a neighborhood of pretty cliffside houses; cycled through the more rural center of the island on cracked, uneven roads; and drove east to Menhaden Lane, a semi-secret beach known by locals and officially designated a boat dock, not a beach. The solid parts of the island offered a certain manicured beauty, but it was common to take a bend or turn right at a crossroads and be in a landscape of untamed beauty. Wild rambling roses bloomed in dense foliage everywhere, and I continued to inhale its scent as I drove.

Finally, I stopped in the city center, as it is, with its municipal buildings, bank and other services, to visit a wonderful second-hand bookshop, Black Cat Books† The store, which moved out of Sag Harbor 10 years ago, carries a great selection of art, design, and photography titles, as well as fiction and other genres, and it’s easy to spend an hour browsing.

After returning the bike, I went back to Marie Eiffel, where I bought an ice cream sandwich and sat on the deck behind the cafe to watch the boats bobbing in the harbor. A sign on a fence read “No Cell Phone Chatter,” which made me smile, but I still had the deck and view to myself.

That feeling of being alone on the island would reoccur during my short stay. So I drove to Reel Point just before sunset. It can be reached by going over a causeway to Ram Island, a stretch of land that extends from the main island into Gardiner’s Bay. On the southeastern tip of Ram Island, a thin stretch of barrier beach – reel point – sticks in the water. The open view of sea, sand and sky was breathtaking, and only me and the plovers enjoyed it.

That evening I lingered on Ram Island to dine at the Ram’s Head Inn, which is under new ownership and a new restaurant that focuses on farm-to-table dishes, but otherwise looks much the same. A 17-room country inn, clad in cedar clapboards, located on four and a half acres overlooking the water. Adirondack chairs were set up in the large backyard and facing west to enjoy the sunset. For the price of my dinner (salmon, 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 per night, with a shared bath.)

In the morning, back at the Chequit, I awoke to a rooster crowing and the sun rising through my window. I wanted to start early: I planned to walk Mashomack . Nature Reserve, over 2,000 acres of tidal creeks, oak forests, freshwater swamps and fields. Forty years ago, the Nature Conservancy and the residents of Shelter Island bundled and bought together what had been private land, leaving nearly a third of the island out of the hands of developers.

Mine was the only car in the parking lot. The walks range from just 0.2 miles to 4.4 miles, and the trails connect so you can compose longer hikes. I plotted a route that took me through the woods and along the edge of a tidal creek, before opening into a vast field. Rambler roses lined parts of the trail, and a breeze blasted their sweet, familiar scent.

Before leaving the island, I meandered all the way west to Crescent Beach, where 25 years ago hotelier André Balazs bought a run-down motel and restaurant and turned it into a sexy beach resort called Beach at sunset that attracts an international party crowd, much to the dismay of the old guard. It marked the first sign of the arrivals. (Rooms go from a low of $479 per night on weekdays to $899 per night on weekends.)

A little further on is the Pridwin, a large white box with a deep front yard that overlooks the bay. The hotel was bought by Cape Resortswho has a track record of taking historic properties, such as Convention Center in Cape May, NJ, and Baron’s Cove in Sag Harborand breathe new life into 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 maintain the look and feel of the hotel, even during the extensive renovations (it opens to guests in July; rooms are over $500 per night in season).

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

As I drove and cycled around the island, I had noticed newly cleared construction sites in wooded areas, which were soon to become new holiday homes. Maybe because I was there during the week, or maybe because peak season hadn’t quite started yet, but to me, even in the midst of these changes, Shelter Island still felt sleepy and uncrowded.

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