A trip to Shelter Island, just outside New York

But with newly renovated hotels, is it time for glitz? A writer gets on his bike to explore.

Shelter Island occupies a tricky position, less than half a mile from Long Island's laid-back North Fork, but also about the same distance from the South Fork - i.e. the Hamptons. Old fortune families who have summered on the small island for generations, as well as the 2,500 year-round residents, view the crowds of the Hamptons as the residents of East Egg watched those of West Egg in "The Great Gatsby". There is always the fear that flashy new money will jump through the water and ruin their quiet paradise.

One ​​summer about 10 years ago, my wife and I stayed at the Chequit Inn, a Victorian-era hotel in Shelter Island Heights that was charming and quaint. We rented bikes and rode the entire 29-square-mile island, which is 90 miles from New York City, or so, exploring beaches and sleepy coves, admiring summer cottages and hitting the only supermarket in the island for sodas and snacks. Everything about this place was chic, casual and timeless.

By The New York Times

Then this In the spring, I learned that the Pridwin Hotel and Cottages, Shelter Island's largest hotel and a mainstay since 1927, was undergoing a major renovation under new ownership. This followed the recent sale and redesign of the Chequit and 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 p.m. I was driving my car on the North Ferry to Greenport (the South Ferry connects the island to the South Fork).

ImageThe Pridwin is one of three hotels on the island that have been recently restored and modernized. Credit... Eric Striffler for The New York Times

I booked a room at the Chequit again. The hotel has been renovated inside and out and now features an inviting patio, a new Asian-inspired restaurant, and a beach beige color scheme instead of the old, dull green colors and white. At $400 a night (on a Monday, no less), it was way 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 settled into my room on the second floor, which had a bird's eye view of the harbor.