Shelter Island is in a delicate location, less than 0.5 miles from Long Island’s laid-back North Fork, but about the same distance from the South Fork, the Hamptons. Old-money families who have spent the summer on a small island for generations, along with 2,500 residents annually, join the Hamptons crowd and East Egg residents in “Great Gatsby” with West Egg residents. I think they are looking the same. There is always concern that flashy new money will jump over the water and ruin their quiet paradise.
About 10 years ago, one summer, my wife and I stayed at a charming, outdated and casual check-it-in at a Victorian hotel in Shelter Island Heights. We rent a bike to ride the entire 29-square-mile island 90 miles from New York City, explore sleepy beaches and coves, view summer villas, and become the island’s only soda and snack supermarket. went. I felt that everything in the place was chic, relaxing and timeless.
And this spring, I learned that Pridwin Hotel and Cottages, the largest hotel on Shelter Island and the flagship since 1927, is undergoing a major refurbishment under new ownership. This followed the recent sale and overhaul of both Chequit and Ram’s Head Inn, another hotel with nearly 100 years of history. Did the glitz come to Shelter Island?
In early June, I set out for a two-day visit. I left my Brooklyn apartment at 10am and was driving to the North Ferry in Greenport by 12:30 (South Ferry connects the island to South Fork).
I booked Chequit’s room again. The interior and exterior of the hotel have been refurbished to feature a cozy patio area, a new Asian restaurant and a beach beige color scheme instead of the old dingy greens and whites. At $ 400 a night (and less on Mondays), it was much more expensive than the funky old Chekit. But it didn’t turn into Nikki Beach at once, and I found the same relaxing atmosphere. I actually checked in to the room on the 2nd floor overlooking the harbor.
Shelter Island may seem like a departure from the Hamptons, but it’s also a wealthy excursion, serving travelers with the means. Prices were particularly high and even exorbitant this summer with record high inflation. I found a $ 45 lobster roll in one lunch menu and paid $ 7 for bottled water and cookies. There are about half a dozen hotels on the island, and Chequit was the cheapest of the three hotels I thought of.
A day trip to Shelter Island by staying in Greenport was previously a more affordable option, but as the town became popular with city dwellers during the pandemic, the hotels there became about as expensive, 1 The average night stay was about $ 330.
But one was a bargain. It’s about renting a bike at the Picozzi bike shop down the hill from my hotel in the village of Daring Harbor. I paid $ 25 for 4 hours and regained 10 times more joy just by bumping all afternoon.
First, I went by bicycle to Marie Eiffel, a village cafe and market popular with islanders and tourists. I ordered a sandwich and pedaled to find a picnic spot along the harbor.
After lunch, I boarded Bahrain and discovered a luxury residential neighborhood by the cliff. Cycling in the central part of the countryside rather than the island on cracked and even roads. Then headed east to Menhadon Lane, a semi-secret beach known to the locals and officially designated as the town’s landing point, rather than the beach. The island’s settlements provided well-maintained cuteness, but it was common to turn around a corner or turn right at an intersection to enter a landscape of pristine beauty. Wild rambler roses bloomed everywhere in the dense leaves, and I continued to breathe their scents while riding.
Finally, we stopped by the town center and visited Black Cat Books, a great second-hand bookstore with services such as the city hall and banks. Relocated from Sag Harbor 10 years ago, the shop offers a wide selection of art, design and photo titles, as well as fiction and other genres, making an hour of browsing easy.
After returning the bike, I returned to Marie Eiffel, bought an ice cream sandwich, sat on the deck behind the cafe and watched the boat sway in the harbor. She smiled when she was scolded by her sign on the fence saying, “I don’t have a cell phone chat,” but she was looking at herself with a deck anyway.
The feeling of being alone on the island recurred during my short stay. For example, I drove to Lille Point just before sunset. It reaches across the causeway to Lamu, a mass of land that stretches from the main island to Gardiners Bay. At a point southeast of Lamu, a thin sliver on Barrier Beach — Lille Point — juts out into the water. The open view of the sea, sand and sky was amazing and only I and the plover enjoyed it.
That night I stayed on Lamu Island and had dinner at Ram’s Head Inn, which has a new owner and a new restaurant focused on cooking from farm to table, but otherwise it looks almost the same. A 17-room country inn covered with cedar shingles, located on a four-and-a-half-acre site overlooking the water. Adirondack chairs lined up in a large backyard, facing west to watch the sunset. At the price of dinner (salmon, glass of Pinogrigio, $ 73 for dessert, chips), I enjoyed the views for millions of dollars. (The cheapest room during my stay was $ 440 per night and the bus was shared.)
Returning to Chequit in the morning, I woke up to the rooster crowing and the sun rising through the window. I wanted to get off to a quick start. I planned to hike the Masomak Nature Reserve, over 2,000 acres of creeks, oak forests, freshwater wetlands and fields. Forty years ago, the residents of Nature Conservancy and Shelter Island united to buy private land, leaving almost one-third of the island out of the hands of the developers.
Only my car was in the parking lot. The hike ranges from 0.2 to 4.4 miles and the trails are connected so you can join long walks together. Before entering the vast fields, I planned a route through the woods and along the edge of the tide cove. Some of the trails were lined with rambler roses, and the breeze evoked their sweet and familiar scent.
Before leaving the island, I shook west to Sunset Beach. Twenty-five years ago, hotel owner André Balazs bought a dilapidated motel and restaurant and turned it into a sexy beachfront resort of the same name that captivates international party spectators. Great for the discomfort of old guards. It showed the first signs of arrival. (Rooms range from $ 479 per night on weekdays to $ 899 on weekends.)
Just below the road is Pridwin, a large white box with a deep vestibule overlooking the bay. The hotel was acquired by Cape Resorts, which has a proven track record of reclaiming and reviving historic buildings such as Congress Hall in Cape May, NJ and Baron’s Cove in Sag Harbor.
Glen Petrie, whose family has owned Pridwin since 1961 and has partnered with Cape Resorts, told me that he felt some pressure from the islanders to maintain the look and feel of the hotel during major refurbishments. (July; rooms will be over $ 500 per night during the season).
“There is no doubt that changes are happening on Shelter Island,” Petrie said. “It is definitely led by the real estate market.”
As I drove around the island and rode my bike, I realized that the newly cleared construction site in the woods quickly became a new villa. Perhaps because I visited that week, or because the high season hadn’t begun completely, Shelter Island felt still drowsy and underpopulated among these changes.
I wanted to come back 10 years later and say the same thing.