Nestled between Long Island’s North and South Forks, Shelter Island is a perfectly dreamy weekend jaunt to the East End that offers a true escape from the bustling city and ever-happening nearby Hamptons. The Chequit is set on a quiet hilltop among some of the most fabulous Victorian cottages.
First built as a religious retreat in 1872, the property was later transformed into a well-regarded getaway in the 1940s, attracting many celebrities and movie stars including Frank Sinatra and Marilyn Monroe. And for good reason. This hotel continues to embody the spirit of its past while also maintaining an authentic yet comfortable experience. In sheer Shelter Island style, it remains genuine to the island’s more rustic, true-to-life sense of heritage while also complementing the other properties on the island like Sunset Beach.
The 37-room retreat is spread over three buildings – the nineteenth century main house and cottage as well as the “summer” house, a six-room neighboring cottage that can be rented by room or by a large group. The design is simple chic featuring a soothing nautical palette of pale blues, pinks, and whites. The rooms are large, airy and include amenities one would expect at a luxury resort such as fine linens, fresh-smelling Bigelow bath products, and attention to details like chic Turkish beach towels and renovated bathrooms and oversized tubs. Comfortable and elegant, yet also maintains the coziness, care, and attention of a small inn. Most rooms feature a private terrace from which you can spot the Milky Way with your naked eyes on clear evening as well as a swing to laze the day and nights away.
As of this summer, The Chequit offers two delectable places to eat. Red Maple serves seasonally inspired New American cuisine with a menu that includes flatbreads, tapas-style plates and grilled fish, chicken and steak in a rustic setting while at the White Hill Cafe, you can enjoy Jack’s coffee, pastries by Brooklyn-based Baked, and wraps and salads to go. Explore other dining options on this low key island which is small enough to easily find your way around.
Not to be missed is Ram’s Head Inn Bar & Restaurant, tucked away in a secluded spot at the end of Ram Island where you can dine al fresco as you enjoy the deliciously prepared seasonal dishes like Crescent Farms duck breast served with black rice, local blueberries and ginger-peach relish on the dining porch or back lawn taking in the splendid sunsets while overlooking the harbor.