A Trip to Shelter Island, Just Outside of New York City

Shelter Island occupies a delicate position, being less than half a mile from Long Island’s laid-back North Fork but also roughly the same distance from the South Fork — i.e., the Hamptons. The old-money families who have summered on the small island for generations, along with the 2,500 year-round residents, regard the Hamptons crowd much the way the residents of East Egg looked upon those of West Egg in “The Great Gatsby.” There is always the worry that the flashy new money will skip across the water and spoil their quiet paradise.

One summer 10 years ago or so, my wife and I stayed at the Chequit Inn, a Victorian-era hotel in Shelter Island Heights that was charmingly outdated and casual.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, give or take, exploring drowsy beaches and coves, admiring the summer cottages and hitting the island’s only supermarket for sodas and snacks. Everything about the place felt chic, relaxed and timeless.

Then, this spring, I learned that the Pridwin Hotel and Cottages, the biggest hotel on Shelter Island and a mainstay since 1927, was getting a major renovation under new ownership. It followed the recent sale and overhaul of both the Chequit and the Ram’s Head Inn, another nearly 100-year-old hotel. Was glitz coming to Shelter Island?

In early June, I set off on a two-day visit to find out. I left my apartment in Brooklyn at 10 a.m., and by 12:30, I was driving my car onto the North Ferry at Greenport (the South Ferry connects the island to the South Fork).

I again booked a room at the Chequit. The hotel has been refurbished inside and out and now features an inviting patio area, a new Asian-inspired restaurant and a beachy beige color scheme instead of the old colors, 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 been turned into Nikki Beach by any stretch, and I found the same relaxed vibe. I practically checked myself into my second-floor room, which had a view down to the harbor.

Shelter Island may see itself apart from the Hamptons, but it’s a similarly wealthy enclave that caters to travelers with means. Prices were especially high, even prohibitive, in this summer of record-high inflation. I spotted 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 hotels on the island, the Chequit was the cheapest out of the…