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A bedroom inside the Chequit. (Credit: Julie Lane)

“We found the Chequit again after it was lost for 60 years.”

That’s how David Bowd describes the $2 million transition that has quietly taken place inside the Chequit since he and Kevin O’Shea acquired the grand Shelter Island hotel from James and Linda Eklund last fall in a $3.35 million deal.

When the doors open on the first 21 guest rooms and suites in the main building on Friday, May 8 — an opening Mr. Bowd refers to as “trial by fire” — the first thing repeat guests will notice is floors have been redone and hallways painted a subtle grey. 

Darker hallways encourage people who may come back to the hotel late at night to keep their voices low so they don’t disturb other guests, Mr. Bowd explained.

All floors have been redone and sleeping rooms have been redecorated. The main building is almost entirely booked for opening weekend.

In designing the hotel rooms, the two heavyweights in the hospitality industry were reaching for a combination of the warmth and intimacy of a bed and breakfast with the independent feel of a hotel.

Mr. Bowd calls it “reinventing the bed and breakfast experience.”

It’s a lesson the men learned with two Salt Hotel properties they operate in Provincetown on Cape Cod.

“A hotel is about great service, a great bed and a great shower,” said Mr. Bowd, who along with Mr. O’Shea, has worked alongside some of the most influential people in the hospitality industry.

Toward that end, 60 percent of his staff comes from Shelter Island with another 20 percent from nearby Greenport to the north and Sag Harbor to the south. That assures guests will get “an insider’s knowledge of Shelter Island,” he said.

Rachel Medina is house manager and he said he wishes he could clone her because of her knowledge of the Island and gracious approach to people. He’s determined that she will be training others who work there to bring the same sensibility to their jobs.

He hopes that the fact that he’s hiring people for year-round employment will give them a feeling of loyalty and belonging that workers in the hospitality field don’t always have because so many can get only seasonal jobs.

“The biggest mistake you can make is not looking after your guests,” Mr. Bowd said about the awareness he and Mr. O’Shea have about successful operation of a hotel like the Chequit.

In tackling the work, Mr. Bowd and Mr. O’Shea wanted to assure that the Chequit would “have a sense of place” reflecting Shelter Island. What they believe they are creating is an inn “on the Island for the Island,” Mr. Bowd said.

He showed off a redecorated room that mirrors what has been done in other rooms throughout the main building. 

A look inside the refurbished Chequit on Shelter Island. (Credit: Julie Lane)
A look inside the refurbished Chequit on Shelter Island. (Credit: Julie Lane)

Rooms are painted a pale pink on top and a subtle grey on the bottom. All rooms have king-sized beds with deluxe custom mattresses and great linens, Mr. Bowd said.

Furnishings are simple with a small ladder adorned with a beach towel and hat the new owners hope guests will use at beaches — and, perhaps by next season — at the Chequit’s own pool.

For those who must stay connected, cellphones can easily be recharged using a plug on one of the bed tables.

A simple marble top table and chairs are poised in a corner that affords a lovely view of the water during the day and a reading lamp for evenings. Many rooms offer water views.

Gone are the plastic molded showers in the bathroom, replaced by glass-doored enclosures. Plumbing has all been updated.

Prices start at $245 per night in the main building.

Still under construction is a new kitchen, restaurant and coffee shop and work will continue on the other two properties with the aim of completion sometime in June.

For those who have spent countless hours drinking at the Chequit, the original bar remains. And the two outdoor levels of the restaurant along with space inside will be called Red Maple, the name taken from a tree that stands in the middle of the highest outdoor level.

The menu will be based on local fresh foods and customers will  be offered both small and large plates.

What the new owners insist on is that the new restaurant won’t have rules that are imposed on customers in some places. You choose what you want and choose to share if you please.

“We’ll just cook great food for you,” Mr. Bowd said. Chef Richard Pims will be the master of the kitchen.

“We’re sensitive to price points” and want people to be able to have a meal at Red Maple without breaking the bank, Mr. Bowd said.

Wines will, of course, be available by the bottle or glass, but for those who order by the glass, they’ll experience something new — wines on tap. They’re not exposed to the air until they hit the glass, so it’s not like drinking a wine that has been open for days, he said.

On Memorial Day Weekend, the new owners look forward not only to their hotel guests, but to meeting more Shelter Island neighbors as they run Chequit Raw, providing a raw bar and wine and champagne on the outer areas of the restaurant.

“It’s a chance to meet our new neighbors,” Mr. Bowd said.

On the side of the main Chequit building bordering Washington Street, the men will be opening White Hill Café featuring Jack’s Stir Brew Coffee, a “good cup of coffee” served in nearby Amagansett and New York City, Mr. Bowd said. They’ll also be serving baked good produced by a Brooklyn company under the name “Baked at Salt.”

Bound for the beach or a picnic? White Hill, which captures the historical name of the area, will offer wraps, salads, spreads and dips to take with you.

Just across Washington Street, is a building that will house both hotel rooms and retail space. The ground floor retail space will be operated by Wampum of Bridgehampton and will offer Chequit-branded clothing items as well as other leisure wear.

Upstairs are rooms  and one bedroom Garden Suite on the third floor that features two full bathrooms and a claw foot tub and private roof terrace. The rooftop suite is priced at the high end at $895 per night. Other rooms are priced in line with those in the main building

The Summer Cottage, behind the main building has six rooms that can be booked individually at $195 per night or for a group. The building was once destined for demolition. Much of the Summer Cottage is already booked by families choosing to take the entire space for their stays, Mr. Bowd said.

“Any renovation is a hard go,” Mr. Bowd said about the efforts made during the last several months.

The Chequit was made that much harder by the brutal winter where the new owners not only had to endure the snow and ice here, but more than 100 inches of snow on Cape Cod. And while they hoped renovation costs might be lower, both know it’s the nature of such projects to end up costing more.