The Grand Hotels Of Shelter Island

The Chequit Inn, celebrating 150 years this year, might be considered the grandest of the grand hotels on Shelter Island. It’s not the biggest, with just 19 rooms in the main structure, but it is the oldest continuously occupied building on the island — and you can’t beat its generalized location, at 23 Grand Avenue. The Carpenter Gothic sits at the center of Shelter Island Heights, like a protector.

Indeed, its history began in God-like fashion, managed by members of the Methodist Church as a meeting hall in 1849. Twenty-three years later, the building expanded and served up meals to the community before becoming a full-fledged inn at the turn of the century.

“The staircase going up to the second and third floors invited me in to explore and imagine all the people who stayed there in the past,” said Stacey Soloviev, director of community relations for the Soloviev Group, which purchased the property two years ago and has been hard at work giving the grand dame a face-lift.

“Renovating The Chequit was the hardest task I have ever done,” Soloviev said. “Once we started, the issues ran into each other, and they seemed endless.”

The difficulty in sourcing materials, and the rising cost, may have slowed down progress, but the intention remained steady. “The restoration mission was very clear from day one. We aimed to pay respect and tribute to such a historic property,” she said. “It was critical that we retain the spirit and legacy of the building but make it better.”

The Soloviev Group also purchased Jack’s Marine Shelter Island, just down the hill, at 188 North Ferry Road, from Jack Calabro’s family, and, more recently, the beloved Shelter Island Heights Pharmacy, known for its old-fashioned soda fountain, next door to the Chequit. Both businesses “will remain the same,” she said.

Soloviev has a lot on her plate, so she’s partnered with Noah Schwartz, who has several of his own restaurants in Greenport, to take care of the restaurants, and with 2,000 acres of farmland, as well as Peconic Bay Vineyard on the North Fork, the Soloviev Group has the resources to supply the restaurants with plenty of fresh food and wine.

“The first-floor restaurant, Weakfish, will open first. It is a noodle-and-sushi-focused restaurant and bar,” she said. “The Tavern will open soon after.”

The Chequit, with its grand front porch offering views of the harbor, will open on Memorial Day. “I know it has been difficult for the neighbors the past two years, and I’m so thankful for their patience,” she said. “We are looking forward to welcoming everyone back at the hotel.”

Some other grand hotels have not been so lucky.

The Prospect Hotel, now Prospect Park, located near the North Ferry, was built in 1872 and burned down in 1922. It was rebuilt in 1924 as the New Prospect Hotel — and burned down again in 1942, on the day it was to be opened for the season.

“In just one hour and 20 minutes from the time that the Shelter Island fire siren was sounded at an early hour on Friday morning, the New Prospect Hotel, the largest and for many years one of the best known summer hotels on the Atlantic Sea, was a mass of smoking ruins,” reported the Long Island Traveler, Mattituck Watchman on July 2, 1942.

Lifelong Shelter Island resident, musician and playwright Lisa Shaw has collaborated with the Shelter Island Historical Society, for the second year in a row, by writing a play based on the five-story, 160-room hotel, which sat on a high bluff overlooking Greenport Harbor. “‘The Prospect of Summer’ will look back at life when the New Prospect Hotel in the Heights was the place to be,” the historical society announced on its website recently.

The idea incubated in Shaw’s head for years before focusing her writing and musical skills on the hotel that had fascinated her since childhood. “It was a huge deal when it burned down,” she said. “But I didn’t want to write about that.”

Instead, she said, “Prohibition is a big part of the play. Back in the day, kids had after-school jobs unloading hooch from boats.

“There was no revenue from alcohol on the books,” she said. “The government was concerned about taxes.” Alcohol was served but not served openly, creating some tension between the two divergent trains of thought.

“It was a very interesting time,” she said. In one scene, a talk titled “The Truth About Alcohol” was presented by the Methodist Church, at the same time as diners were imbibing at the hotel, with the hotel manager caught in the middle.

“The church was a huge community influencer, while hotels brought people from the city with different sensibilities,” said Shaw. The hotel had 200 cabanas on the beach, located near North Ferry, so guests came from New York City and Brooklyn by train to Greenport, hopped the ferry and walked to the hotel, where they could relax in 200 beach cabanas.

She was hesitant to give away too much; however, she did cop to a murder being part of the musical.

Two hundred and fifty tickets go on sale Wednesday, June 1, at the Shelter Island Historical Society, and the play will be presented on Saturday, July 23, through Monday, July 25, outdoors, on the Shelter Island History Center stage.

The Manhanset House Hotel, sadly, had a similar fate. It was built in 1874 on another bluff just east of Locust Point, with additions along the way. By all accounts, it was enormous. Housing 500 guests, it stretched over 700 feet long, spread out over three parts, including two-, four- and five-story buildings, a dance hall pavilion, and cottages in the rear.

In the early morning hours of August 18, 1896, a fire started in the laundry room of the original structure. “The fire department from this village, aided by the stream of water thrown on the flames from the steam yachts and other steam craft in the bay, preserved the newer portion of the hotel and also the annex,” reported The New York Times.

The Manhanset was resurrected the following year, but in summer 1910, weeks before it was to open for the summer season, it was struck by lightning and burned to the ground. Thankfully, no one died in any of the fires — and boxes of liquor were saved.

In the late 1800s, farmers from Sag Harbor drove sheep across the causeway, navigating only at low tide on a full moon. “There were no natural predators, so they got fat,” said Aandrea Carter, the new owner of the Ram’s Head Inn.

“I’m a Midwestern girl,” the Sag Harbor resident said. “The Hamptons are such a beautiful place. It’s a lot like Iowa if you remove the water.”

She was awestruck by the grounds, at 108 Ram Island Drive, even before stepping inside the 22-room inn. “I enjoyed the gentility of it all,” she said.

Cruising Ram’s Island Drive, there are so many ospreys in flight, Ram’s Head Island should be renamed Osprey’s Island. It is utterly peaceful. The inn sits atop of a bluff, of course, overlooking Coecles Harbor and Gardiners Bay.

On a cool day in April, the fireplaces in the common areas were roaring and neatly dressed staff were readying the inn for an event and preparing for their second season. Her team had updated the rooms with new mattresses, sheets and carpets, adding period furniture with modern upholstery, and painted every inch of the place.

Dining room doors open to the outside covered porch. Chef Joe Smith was retained in the kitchen, and the many working organic gardens play a large role in the menu. There’s a 900-foot beach for frolicking, and oysters are being cultivated under the dock, but those are not on the menu. The bivalves actually help to keep the waters clean.

“Our mission this year is ‘Detox to Retox,’” said Carter, who’s adding a Wellness Program. “A glass of wine, a bite of chocolate, is a sustainable practice, if you just work out a little more.”

Said Carter, “We’re living in a crazy time. We need a place to go. It’s an intended effort to come, but once you cross the threshold, it’s like an exclusive club.”

Joan Covey, a New York City Realtor, crossed the threshold in 1919 to buy the 4-acre-plus property, but it appears she didn’t build her hotel until a decade later. “Anyone would have been taken by boat,” said Carter.

Not a lot is known about Covey, in an era when women were not known to be in business, though much has been speculated. “Was she a bootlegger? Could she have been a madam?” Carter asked. “Who would build on an island off an island, off an island?”

Whatever Covey was doing, the inn survived the Depression and went on to become a sought-after destination for the elite despite, or perhaps because of, its isolated location.

In the summer of 1947, 25 of the country’s top physicists gathered at the Ram’s Head, where Willis Lamb turned the science world on its head by introducing his new theory of quantum electrodynamics, later termed the “Lamb Shift.”

In 1975, New York Governor Hugh Carey and his family rented the entire inn, while their own home was being renovated. According to The New York Times, “The Careys have made a business opportunity as well as a summer haven out of the inn by leasing the entire building, operating its restaurant and bar, and renting out 17 rooms on the second floor to paying guests. The family uses the smaller third floor for its own quarters.”

The Pridwin, at 81 Shore Road, may have been one of the last grand hotels to be built on Shelter Island, but in many ways it has become the biggest part of the local community. The structure isn’t fancy, but it does sit on a bluff, above Crescent Beach, overlooking Peconic Bay.

It’s been owned by the Petry family since 1961. The family’s move from the city was very “Green Acres,” since Dick Petry wanted out of the city and his new wife, Edie, was not so keen about the idea of moving to a small island.

The Petrys grew to become part of the island, nonetheless, hosting events for local organizations like the fire and ambulance departments, Little League and the like. There’s never a mention of the Pridwin without its famous Wednesday night barbecues on the beach and dancing afterward, for both guests and locals.

A British company bought the property in 1927 and named it after King Arthur’s Shield but ran out of money before they got to develop the 7-plus acres. “I always thought it was because the land was protected, shielded from the elements in all ways,” said Glenn Petry, of the hotel’s logo.

The eldest of two sons, Petry wasn’t born at the hotel, but his parents took him there from the hospital, soon after his family acquired it. He went to school on the island until his teenage angst couldn’t take the long, stifling winters anymore.

The Pridwin Hotel and Cottages, like most of Shelter Island’s grand hotels, was a seasonal operation — but that’s about to change. The family recently partnered with Cape Resorts, owners of Baron’s Cove in Sag Harbor and many other East Coast resorts.

“I wasn’t looking, but a person I trusted asked me if I had met Curtis Bashaw,” he said, of Cape Resorts’ CEO. “We had lunch in the city, and he told me his story, very similar to mine.”

Bashaw’s paternal grandparents started the family’s hotel operation with Congress Hall, in Cape May, a seaside resort town at the tip of southern New Jersey’s Cape May Peninsula, known for its grand Victorian structures, not unlike Shelter Island, and much like Petry’s maternal grandparents, who originally invested in the Pridwin.

Needless to say, the two men hit it off. “They invited us down to Congress Hall in 2017 or 2018, at Christmastime,” said Petry. “It was impeccable, and it’s 50 years older and 50 percent larger than the Pridwin.

“They took a seasonal hotel and made it into a year-round destination,” said Petry. “We’ve always wanted to do that with the Pridwin.”

It helped that the two families had shared values. They believe in the same things, such as heritage and longevity, and integrating into the community.

“It was a match I didn’t think was possible. Dad’s interest perked up too, and we agreed to talk about partnership,” he said. “Curtis was a unicorn for us. He’s a very unique and genuine guy. That helped guide us through complexities.”

Renovations have been underway for a couple of years, and it will open this summer with a whole new vibe, but with the same classic Adirondack camp style it’s known for, including white painted facade and hunter green trim.

Colleen Bashaw, Curtis’s sister, oversees redecorating and has recycled treasures from the past, from Petry family photos to the original wainscoting, hardwood floors and chandeliers. The spa is new.

The 16 private cottages will have wood-burning fireplaces, kitchenettes and private decks with water views. “The water out front is my favorite place to swim,” said Petry. “I’ve traveled a lot, and jumping off the Pridwin dock is still my favorite place.”