Historic Chequit Reopens on Shelter Island with Many Updates, 3 New Restaurants

The Chequit got a facelift in time for its 150th anniversary
The Chequit got a facelift in time for its 150th anniversary
Photo by Zack DeZon

The reopening of the historic Chequit has created a stir on Shelter Island, with residents and visitors alike clamoring for a peek inside the newly renovated hotel that has been an integral part of the island’s history for 150 years.

Overlooking Dering Harbor in Shelter Island Heights, the Chequit reopened on Memorial Day weekend with three new restaurant-and-beverage concepts along with major updates that respect the storied history of the building.

“Everybody is so excited to see The Chequit back to life,” said Stacey Soloviev, director of community relations for the Soloviev Group, which purchased the property at auction in March 2020 and soon undertook a major renovation. The Soloviev Group owns several properties on the East End, including Peconic Bay Vineyards and Santa’s Christmas Tree Farm, both in Cutchogue.

The Chequit includes a main building with 19 renovated guest rooms and two additional buildings with a combined 16 guest rooms.

The overhaul concentrated primarily on the main building, which houses the main lobby and the restaurants.

“For me, the most important aspect was that the lobby feel like a living room that welcomes people to the hotel and the island — where guests could mingle with locals and feel the area and the place,” Soloviev said.

Designed with soft shades of white and beige, the inviting lobby flows into the restaurants, which are led by Chef Noah Schwartz and include Weakfish Sushi & Noodle, featuring New Asian cuisine.

“Chequit” is a Native American word for weakfish, a white fish that abounded in the Peconic Bay when the property first opened in 1872. Weakfish Sushi & Noodle’s menu includes sushi rolls, sashimi and ramen dishes, with pork, chicken, seafood and vegetable choices.

Heights Café & Wine Bar, named for The Chequit’s Shelter Island Heights location, is a coffee shop with homemade pastries by day that morphs into a wine bar with a selection of wines, cheese boards and light bites by late afternoon.

The Tavern is a New American concept with a farm-to-table menu featuring steaks, homemade pasta dishes, seafood platters, pulled duck BBQ, filet mignon sliders, smashburgers and a raw bar.

Serving lunch and dinner, The Tavern includes a large center bar and an antique billiard table that came from The Chequit’s original dining room.

All of the eateries feature outdoor seating options, which was an important focus in the redesign, according to General Manager Ben Levine.

Dining al fresco is served with a view at the Chequit
Dining al fresco is served with a view at the ChequitPhoto by Zack DeZon

“Outdoor dining has always been part of The Chequit, where people have always enjoyed lounging around the beautiful wraparound porch, eating fresh food and drinking cocktails,” Levine said. “But the pandemic definitely gave us a push to put an extra emphasis on outdoor dining.”

Weakfish opens to a newly created back terrace, while there are four new semi-private dining areas with water views.

“We’ve added fire pits, which will allow for outdoor dining into the fall months,” Levine said. “As anyone who spends time out here knows, September and October are magical times to be on the East End, especially Shelter Island.”

The guest rooms were redesigned with soft lighting and muted shades of white for a coastal feel, with shiplap walls and oars serving as guest room signs. Tubs were added to some of the bathrooms, which also feature elements like rain showers and glass partitions.

“We also brought the rooms up to modern expectations, with central air conditioning, heating and soundproofing and the addition of mini fridges and TVs,” Levine said. Free Wi-Fi is also available throughout The Chequit.

In its early days, the property served as a gathering place for members of the Methodist Church who came to the island on summer retreat and stayed in nearby cottages. The cottages did not have kitchens, so the visitors had all their meals at the property, which they simply called “The Restaurant.”

The Chequit became an inn in the early 20th century and soon earned a reputation for live music and late-night parties. Over the years, it played host to celebrities, including Marilyn Monroe, Arthur Miller and a Kennedy or two.

“The building is celebrating its 150th anniversary this year, and it hasn’t gotten much more than a facelift in the last 50 to 70 years, so it was long overdue for the love and the work that Stacey put into it,” Levine said.

Community is one of the pillars of the Soloviev Group, from hiring local to working with other businesses in the area. The Chequit started a new artist-in-residence program this summer that will feature the work of East End artists in the lobby, restaurants and a newly created exhibition gallery. The property also offers local products, such as fresh juices from The Giving Room in Southold and donuts from Dreesen’s in East Hampton, and is planning to collaborate with local winemakers on food pairings.

“Every local has a ‘Chequit first’ story, such as their first kiss or their first beer, and having the local community come by and seeing their faces of shock and awe at what has been done — it is incredibly rewarding to be a part of this project and be able to provide this experience to the community,” Levine said. 

More from Our Sister Sites