Shelter Island occupies a fragile place, being lower than half a mile from Lengthy 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 best way the residents of East Egg seemed upon these of West Egg in “The Nice Gatsby.” There’s at all times the concern that the flashy new cash will skip throughout the water and spoil their quiet paradise.
One summer season 10 years in the past or so, my spouse and I stayed on the Chequit Inn, a Victorian-era resort in Shelter Island Heights that was charmingly outdated and informal. We rented bikes and rode everywhere in the 29-square-mile island, which is 90 miles from New York Metropolis, give or take, exploring drowsy seashores and coves, admiring the summer season cottages and hitting the island’s solely grocery store for sodas and snacks. Every little thing in regards to the place felt stylish, relaxed and timeless.
Then, this spring, I discovered that the Pridwin Resort and Cottages, the most important resort on Shelter Island and a mainstay since 1927, was getting a significant renovation beneath new possession. It adopted the latest sale and overhaul of each the Chequit and the Ram’s Head Inn, one other almost 100-year-old resort. Was glitz coming to Shelter Island?
In early June, I set off on a two-day go to to seek out 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 resort has been refurbished in and out and now options an inviting patio space, a brand new Asian-inspired restaurant and a beachy beige shade scheme as a substitute of the previous colours, dingy inexperienced and white. At $400 an evening (on a Monday, no much less), it was far more costly than the funky previous Chequit. But it surely hadn’t been changed into Nikki Seaside by any stretch, and I discovered the identical relaxed vibe. I virtually checked myself into my second-floor room, which had a view right down to the harbor.
Shelter Island might even see itself other than the Hamptons, however it’s a equally rich enclave that caters to vacationers with means. Costs have been particularly excessive, even prohibitive, on this summer season 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 lodges 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 was a extra inexpensive choice, however as that city has turn out to be extra common with metropolis dwellers throughout the pandemic, lodges there have turn out to be almost as costly, averaging round $330 an evening.
However one factor remained a cut price: renting a bicycle at Piccozzi’s Bike Store, down the hill from my resort within the village of Dering Harbor. I paid $25 for 4 hours and obtained 10 occasions that again in pleasure simply bumming round all afternoon.
First, I cycled over to Marie Eiffel, a restaurant and market within the village common 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 recognized to locals and formally designated a city touchdown, not a seaside. The settled elements of the island supplied a sure manicured prettiness, however it was widespread to go round a bend or flip proper at a crossroads and be in a panorama of untamed magnificence. Wild rambler roses have been blooming all over the place in dense foliage and I stored inhaling the perfume of them as I rode.
Lastly, I finished into the city heart, equivalent to it’s, with its municipal buildings, financial institution and different providers, 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 simple to spend an hour searching.
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. An indication posted on a fence scolded “No Cell Telephone Chatter,” which made me smile, however I had the deck and think about to myself anyway.
That sense of being alone on the island would occur repeatedly throughout my brief keep. As an example, I drove out to Reel Level simply earlier than sundown. It’s reached by going over a causeway to Ram Island, a piece of land extending off the primary island into Gardiner’s Bay. At Ram Island’s southeasterly level, a skinny sliver of barrier seaside — Reel Level — juts into the water. The open view of sea, sand and sky was beautiful, and it was simply me and the piping plovers to get pleasure from 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 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 have been lined up within the huge yard and dealing with west to soak up the sundown. For the worth 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.)
Within the morning, again on the Chequit, I woke to a crowing rooster and the rising solar by my window. I wished to get an early begin: I deliberate to hike Mashomack Nature Protect, 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, protecting virtually a 3rd of the island out of the fingers of builders.
Mine was the one automotive within the parking zone. The hikes vary from as brief as .2 miles to 4.4 miles, and the paths join so you possibly can piece collectively longer walks. I plotted a route that took me by forest and alongside the sting of a tidal creek, earlier than opening into an enormous discipline. Rambler roses lined elements of the path, and a breeze kicked up their candy, acquainted scent.
Earlier than I left the island, I swung all the best way west to Sundown Seaside, 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 title that pulls a world occasion 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 as much as $899 an evening on the weekend.)
Simply down the street sits the Pridwin, an enormous white field with a deep entrance yard overlooking the bay. The resort was purchased by Cape Resorts, which has a monitor document of taking historic properties, like Congress Corridor in Cape Could, 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, advised me he felt a sure strain from islanders to retain the feel and appear of the resort, even amid the intensive renovations (it opens to company in July; rooms can be greater than $500 an evening in season).
“There’s no query that there’s change afoot on Shelter Island,” Mr. Petry mentioned. “It’s undoubtedly being led by the true property market.”
Driving and biking across the island, I’d seen freshly cleared constructing websites in wooded areas, quickly to turn out to be new trip properties. Maybe as a result of I visited throughout the week, or maybe as a result of the excessive season hadn’t absolutely begun, however Shelter Island, to me, even amid these adjustments, nonetheless felt drowsy and unpopulated.
I hoped to come back again once more in one other 10 years and say the identical factor.