The Shelter Island List

Next to the Hamptons and between the North and South Forks of Long Island, Shelter Island blends the upscale vibe of the Hamptons with the approachable and low-key temperament of the North Fork. With water at nearly every turn—from harbors to hidden ponds and dense marshlands—the 12-square-mile island is a sanctuary for wildlife and small enough for a visitor to develop the kind of intimate familiarity with a place that seems to have been lost in the modern era. My life-partner, Cian Connor, and I went back to Shelter Island for a late August weekend getaway from the Hamptons, where we spend many summer weekends.

The short ferries from Greenport or North Haven required to get to the island create just enough friction to keep out anyone who truly doesn’t want to be here. Time on Shelter Island seems to move at its own pace—and we are a fan of this. While many mom and pop establishments are still in business, during the pandemic Shelter saw a boom in new restaurants, coffee shops, and hotels.

THE STAY

While we usually stay with friends on the island, we decided this time to book a room at The Pridwin. Located on the water with beautiful bay views towards Greenport, the Pridwin was built in 1927 but recently reopened after a two-year renovation. The owner, Curtis Bashaw, and his team went to great lengths to preserve the bones of the main house, which combines vintage American style with a modern color palette and conveniences. He wants to make this place a year-round destination. 

EAT & DRINK

Leon 1909:  Our best meal was at Leon 1909, a newly opened restaurant featuring French-Italian cuisine which the chefs cook mostly out of a huge hearth in the dining room. Walking into Leon is a sensory overload in the best way, with its wood-fire aromas. We had crab gougeres, sweet corn and lobster pasta and a slowly wood-fire roasted chicken—all delicious! We’ve long found Hamptons restaurants to be much more of a scene than quality—rather confounding, as the produce on the East End is fantastic. At Leon, they have really nailed variety and quality and our waiter, Alex, was fabulous and knew the menu backwards and forwards.

Vine Street Cafe: This is a place we have been coming to for eight years. It’s a year-round, family-owned farm-to-table restaurant that highlights the best of local food purveyors and winemakers in the area. It is great for a summer meal seated outside on the graveled patio or in the winter for a warm and cozy experience in the dining room. The best picks on the menu are the fish and pasta dishes! They also have a great bar with a mean martini. 

Rams Head Inn: Perfect for sunset drinks! Rams Head Inn is located on Coecles Harbor, a sheltered enclave right next to Garninders Bay. There are many Adirondack chairs on the lawn where you can enjoy a cocktail and watch the sunset. Ownership has recently changed hands and we have not yet tried the food, but have heard good things. 

Salt: Salt is right on a small marina right next to a small boatyard, making it easy to pull up a boat for pickup or dine-in with a menu of oysters, clams, tuna sandwiches and its famous lobster roll. Most of Salt’s seating is outdoors and under a canopy and all of it is casual. Next to it is Shipwreck Bar, with live music many nights of the week during the summer. This is a seasonal restaurant, open from late spring until the first week of October. 

Sunset Beach: An iconic destination for day or nighttime cocktails. This is the only place on Shelter Island that somewhat counts as nightlife. Located right on the bay with a sandy beach, Sunset Beach is quite the vibe in the summer, especially at night where there is always a DJ next to the rooftop bar. We have been here countless times and are happy it’s back open after a couple of years of uncertainty. 

Marie Eiffel Market: In many ways the social nucleus of Shelter Island, Marie Eiffel is the go-to breakfast and lunch destination for both locals and visitors. Although some things are absurdly expensive (it’s $2 extra if you want a splash of oat milk in your iced coffee!) for the most part it is worth it. The market is located on a marina and has seating on the dock with a stunning view of vintage boats sailing by. Our favorite things to get are the blueberry muffin, Marie’s omelet, Cuban sandwich, and the Croque Madame sandwich. 

DISTRACTIONS

We went biking all around the island and stopped at various ponds and secluded beaches. One special place was “Crab Creek Beach,” named after the small creek populated by plenty of Blue Crabs (you need to have a fishing license in order to take these home with you). 

During the weekend, we also had an amazing boat day. Friends picked us up on the dock at The Pridwin and we headed straight to Salt to pick up lunch (lobster rolls, fries, oysters, and shrimp cocktail) along with some amazing libations. Lunch was served after we anchored in Coecles Harbor with unspoiled views of the Mashomack Preserve. We finished the day with lots of swimming in the warm water. 

Beachgoers love Crescent Beach. The hotel and restaurant Sunset Beach is located right on the water (the hotel also manages a portion of the beach), so you have the option to book a table for lunch at the French Riviera-inspired restaurant. Silver Beach and Wade Beach are also worthwhile. Hay Beach is a more peaceful option and is located right by Ram and Little Ram islands (the peninsula side of Shelter Island). Some beaches require a day permit, which can be easily purchased from the town’s website.

Finally, if you are looking for nature immersion, you can hike the many trails in the Mashomack Preserve.