Shelter Island occupies a fragile place, being lower than half a mile from Long Island’s laid-back North Fork but additionally roughly the identical distance from the South Fork — i.e., the Hamptons. The old-money households who’ve summered on the small island for generations, together with the two,500 year-round residents, regard the Hamptons crowd a lot the way in which the residents of East Egg seemed upon these of West Egg in “The Great Gatsby.” There is at all times the fear that the flashy new cash will skip throughout the water and spoil their quiet paradise.
One summer time 10 years in the past or so, my spouse and I stayed on the Chequit Inn, a Victorian-era lodge in Shelter Island Heights that was charmingly outdated and informal. We rented bikes and rode all around the 29-square-mile island, which is 90 miles from New York City, give or take, exploring drowsy seashores and coves, admiring the summer time cottages and hitting the island’s solely grocery store for sodas and snacks. Everything in regards to the place felt stylish, relaxed and timeless.
Then, this spring, I realized that the Pridwin Hotel and Cottages, the largest lodge on Shelter Island and a mainstay since 1927, was getting a major renovation beneath new possession. It adopted the current sale and overhaul of each the Chequit and the Ram’s Head Inn, one other practically 100-year-old lodge. Was glitz coming to Shelter Island?
In early June, I set off on a two-day go to to discover out. I left my house in Brooklyn at 10 a.m., and by 12:30, I used to be driving my automotive onto the North Ferry at Greenport (the South Ferry connects the island to the South Fork).
I once more booked a room on the Chequit. The lodge has been refurbished inside and outside and now options an inviting patio space, a brand new Asian-inspired restaurant and a beachy beige shade scheme as an alternative of the outdated colours, dingy inexperienced and white. At $400 an evening (on a Monday, no much less), it was way more costly than the funky outdated Chequit. But it hadn’t been changed into Nikki Beach by any stretch, and I discovered the identical relaxed vibe. I virtually checked myself into my second-floor room, which had a view down to the harbor.
Shelter Island may even see itself aside from the Hamptons, nevertheless it’s a equally rich enclave that caters to vacationers with means. Prices had been particularly excessive, even prohibitive, on this summer time of record-high inflation. I noticed 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 motels on the island, the Chequit was the most affordable out of the three I thought of.
Staying in Greenport and day tripping to Shelter Island used to be a extra reasonably priced choice, however as that city has develop into extra standard with metropolis dwellers in the course of the pandemic, motels there have develop into practically as costly, averaging round $330 an evening.
But one factor remained a cut price: renting a bicycle at Piccozzi’s Bike Shop, down the hill from my lodge within the village of Dering Harbor. I paid $25 for 4 hours and received 10 instances that again in pleasure simply bumming round all afternoon.
First, I cycled over to Marie Eiffel, a restaurant and market within the village standard with islanders and vacationers alike. I ordered a sandwich then pedaled off to discover a picnic spot alongside the harbor.
After lunch, I rode up Harbor Lane, discovering a neighborhood of fancy homes perched on the cliffside; cycled down the island’s extra rural midsection on cracked, uneven roads; and rode east to Menhadn Lane, a semi-secret seaside identified to locals and formally designated a city touchdown, not a seaside. The settled elements of the island supplied a sure manicured prettiness, nevertheless it was frequent to go round a bend or flip proper at a crossroads and be in a panorama of untamed magnificence. Wild rambler roses had been blooming in all places in dense foliage and I stored inhaling the perfume of them as I rode.
Finally, I ended into the city middle, equivalent to it’s, with its municipal buildings, financial institution and different companies, to go to an exquisite used e-book retailer, Black Cat Books. The store, which moved from Sag Harbor 10 years in the past, has a big choice of artwork, design and pictures titles, in addition to fiction and different genres, and it’s straightforward to spend an hour looking.
After I returned the bike, I went again to Marie Eiffel, the place I purchased an ice cream sandwich and sat on the deck behind the café, watching the boats bob within the harbor. A signal posted on a fence scolded “No Cell Phone Chatter,” which made me smile, however I had the deck and consider to myself anyway.
That sense of being alone on the island would occur repeatedly throughout my quick keep. For occasion, I drove out to Reel Point simply earlier than sundown. It’s reached by going over a causeway to Ram Island, a piece of land extending off the principle island into Gardiner’s Bay. At Ram Island’s southeasterly level, a skinny sliver of barrier seaside — Reel Point — juts into the water. The open view of sea, sand and sky was beautiful, and it was simply me and the piping plovers to take pleasure in it.
That night, I lingered on Ram Island to have dinner on the Ram’s Head Inn, which has a brand new proprietor and a brand new restaurant specializing in farm-to-table dishes, however in any other case appears to be like a lot the identical. A 17-room nation inn clad in cedar shingles, it’s located on 4 and half acres overlooking the water. Adirondack chairs had been lined up within the massive yard and dealing with west to take within the sundown. For the value of my dinner (salmon, a glass of pinot grigio and dessert for $73, plus tip), I loved the million-dollar view. (The most cost-effective room on the time of my keep was $440 an evening, with a shared bathtub.)
In the morning, again on the Chequit, I woke to a crowing rooster and the rising solar by means of my window. I wished to get an early begin: I deliberate to hike Mashomack Nature Preserve, greater than 2,000 acres of tidal creeks, oak woodlands, freshwater marshes and fields. Forty years in the past, the Nature Conservancy and the residents of Shelter Island banded collectively and purchased what had been privately owned land, holding virtually a 3rd of the island out of the palms of builders.
Mine was the one automotive within the parking zone. The hikes vary from as quick as .2 miles to 4.4 miles, and the paths join so you’ll be able to piece collectively longer walks. I plotted a route that took me by means of forest and alongside the sting of a tidal creek, earlier than opening into an unlimited discipline. Rambler roses lined elements of the path, and a breeze kicked up their candy, acquainted scent.
Before I left the island, I swung all the way in which west to Sunset Beach, the place 25 years in the past, the hotelier André Balazs purchased a dilapidated motel and restaurant and turned it into a horny beachfront resort of the identical identify that attracts a world get together crowd, a lot to the old-guard’s displeasure. It marked the primary signal of the arrivistes. (Rooms go from a low of $479 an evening on weekdays up to $899 an evening on the weekend.)
Just down the highway sits the Pridwin, a giant white field with a deep entrance yard overlooking the bay. The lodge was purchased by Cape Resorts, which has a monitor file 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 household has owned the Pridwin since 1961, and who has partnered with Cape Resorts, instructed me he felt a sure stress from islanders to retain the feel and appear of the lodge, even amid the intensive renovations (it opens to company in July; rooms might be greater than $500 an evening in season).
“There’s no question that there’s change afoot on Shelter Island,” Mr. Petry mentioned. “It’s definitely being led by the real estate market.”
Driving and biking across the island, I’d seen freshly cleared constructing websites in wooded areas, quickly to develop into new trip properties. Perhaps as a result of I visited in the course of the week, or maybe as a result of the excessive season hadn’t totally begun, however Shelter Island, to me, even amid these modifications, nonetheless felt drowsy and unpopulated.
I hoped to come again once more in one other 10 years and say the identical factor.
