Shelter Island is less than half a mile from the North Fork of Long Island but also less than a mile from the South Fork. They are worried that the new money will ruin their quiet paradise and leave them penniless.
A decade ago, my wife and I stayed at the Chequit Inn, a Victorian-era hotel in Shelter Island Heights that was charmingly outdated and casual.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 all over the 29- square-mile island, which is 90 miles from New York City and is home to the only supermarket on the island. The place was chic and relaxing.
The Pridwin Hotel and Cottages, Shelter Island's biggest hotel and a mainstay since 1927, was being renovated under new ownership. The Chequit and the Ram's Head Inn are both over 100 years old. Shelter Island was rumored to be the location of a new movie.
I went on a two day visit in June to find out. I left my apartment in Brooklyn at 10 a.m. and drove my car onto the North Ferry at Greenport at 12 noon.
There is a room at the Chequit. The hotel has been refurbished inside and out and now has an inviting patio area, a new Asian-inspired restaurant and a beachy beige color scheme. It was more expensive than the Chequit at $400 a night. I found the same relaxed vibe even though it hadn't been turned into a beach. I could see the harbor from my second floor room.
Shelter Island is a wealthy area that caters to travelers with means. In this summer of record-high inflation prices were high. I paid $7 for a bottle of water and a cookie after seeing a lobster roll on the menu. The Chequit was the cheapest hotel on the island.
As Shelter Island has become more popular with city dwellers during the Pandemic, hotels there have become nearly as expensive as they used to be.
Renting a bicycle at the bike shop down the hill from my hotel was a good deal. I paid $25 and got 10 times that back in pleasure.
Marie Eiffel is a cafe and market popular with islanders and tourists. I found a picnic spot along the harbor after ordering a sandwich and riding a bike.
After lunch, I rode up Harbor Lane, discovering a neighborhood of fancy houses perched on the cliffside, cycling down the island's more rural midsection, and riding east to Menhadn Lane, a semi- secret beach known to locals. It was common to go around a bend or turn right at a crossroads and be in a landscape of untamed beauty. I was inhaling the scent of wild rambler roses as I rode and they were in bloom.
Black Cat Books is a wonderful used book store that is located in the town center. A large selection of art, design and photography titles, as well as fiction and other genres, is available at the shop, which moved from Sag Harbor 10 years ago.
I went back to Marie Eiffel to buy an ice cream sandwich and watch the boats in the harbor. I had the deck and view to myself even though the sign on the fence said no cell phone chatter.
I felt like I was alone on the island a lot during my stay. I went to Reel Point before the sun set. It is reached by crossing a causeway to Ram Island, a piece of land that extends off the main island into the bay. There is a small piece of barrier beach at the southeasterly point. It was just me and the piping plovers that enjoyed the view of the sea, sand and sky.
The Ram's Head Inn on Ram Island has a new owner and a new restaurant that focuses on farm-to-table dishes. The country inn is located on four and half acres and overlooks the water. There were Adirondack chairs lined up in the backyard to watch the sunset. I enjoyed the million-dollar view for the price of my dinner. The cheapest room I stayed in was $440 a night with a shared bath.
I woke up to a rooster crowing and the sun setting through my window. I was going to hike the more than 2,000 acres of the Mashomack Nature Preserve. Almost a third of Shelter Island was kept out of the hands of developers when the Nature Conservancy and the residents banded together in the 40s.
There was only one car in the lot. The hikes range from.2 miles to.4 miles and the trails connect so you can walk longer. I plotted a route that took me through a forest and along the edge of a tidal creek. A breeze kicked up the scent of rambler roses as they lined the trail.
When I left the island, I went all the way west to Sunset Beach, which is a sexy beachfront resort that attracts an international party crowd. It signaled the beginning of the arrivistes. Rooms go from a low of $479 a night on weekdays to $899 a night on the weekends.
The Pridwin is a big white box with a view of the bay. Congress Hall in Cape May, N.J., and Baron's Cove in Sag Harbor are two historic properties that have been revived by Cape Resorts.
Glenn Petry, whose family has owned the Pridwin since 1961, told me he felt pressure from islanders to retain the look and feel of the hotel despite the extensive renovations.
There is change afoot on Shelter Island. The real estate market is leading it.
Freshly cleared building sites are soon to become new vacation homes. Shelter Island was still sleepy and unpopulated despite the changes that had taken place.
I wanted to say the same thing again in another decade.
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