Shelter Island

For Hamptons visitors, Shelter Island [aka “The Rock”] isn’t always a popular destination during the winter season. Nestled between the North and South Forks of Long Island and surrounded by the Shelter Island Sound and Gardiners Bay, “The Rock” can be reached via a short ferry ride either from Greenport or from North Haven.  If you know where to go, spending an afternoon and evening on Shelter Island is a really fun, romantic way to spend a Sunday afternoon.  Here’s the KDHamptons insider guide to Shelter Island, including my favorite secret spots.


FERRY PHOTO OPP: Hamptons visitors can drive on to the Shelter Island Ferry in North Haven. It’s only a five minute ferry ride so get out of the car and take in the beautiful views. The light is always great any time of the day so snap away.  Even though “The Rock” is just a quick hop across the water, taking the ferry makes it feel like you are going on a mini island vacation.

GO TAKE A HIKE: Start your island visit with an incredible hike. Nearly one-third of the 27.1 square mile island is owned by The Nature Conservancy, and preserved in a wild state at Mashomack Preserve . Hike one of four fantastic nature and bird-watching trails, from 1.5 miles to 11 miles along the coastline of the island and you won’t believe you’re in the Hamptons anymore. Keep your eyes peeled for hawks, osprey, and the elusive eagle that lives on the island and plenty of Instagramable views.


SNACK TIME: PIZZA PIZZA! Marie Eiffel Market [below] makes the best hand-rolled pizza on the island.  She also offers fresh baked goods, organic produce, groceries, grass-fed & organic meats, imported cheeses, & fresh fish, signature sandwiches, homemade salads. Take out or stay and eat at the café, and when the temps warm up you can relax out back, dockside. Location: 184 N. Ferry Road, Shelter Island, NY;11964; (631) 749-0003.  Psst! Marie Eiffel also has a super chic fashion boutique on the island as well.

marie eiffel

DRIVING DERING HARBOR: Dering Harbor is a charming private village and picturesque harbor that was named after Thomas Dering, a prominent Boston merchant who married Mary Sylvester of Shelter Island’s founding family in 1756. Not many people know about this little village which maintains only 64 summer residents, and 13 in winter! Dering Harbor lies on the north side of Shelter Island facing Greenport, and boasts some of the most pristine architectural estates you will ever see.

dering harbor

shelter island

SLEEP TIGHT: If you want to spend the night, there are a few great inns on the island that stay open during the off-season months to check in to after your drive the island.  Seven is a casual boutique hotel, bed and breakfast where high design updates a welcoming 1902 farmhouse. Renovated guest rooms feature sumptuous bedding with fresh white duvets and goose down comforters, and sustainable toiletry amenities from The Cold Spring Apothecary. Contemporary bathrooms feature minimalist German fixtures and design inspired glass-tile walk in showers.  A European-inspired breakfast buffet includes: warm croissants, fresh fruits, juices, organic honey, and local organic eggs from the neighbors chicken coop. Location: 7 Stearns Point Road Shelter Island, Long Island, NY 11965 Tel (347) 326-3259.


VINE DINING: Vine Street Cafe [below] is the most sophisticated restaurant on the island. Chef and owners Lisa & Terry Harwood make everything in-house, working with area farmers, fishermen & vineyards on his seasonal menus. Terry and Lisa’s desserts, ice creams and fruit crisps are no exception. Vine Street Café 41 South Ferry Road, Shelter Island, NY 11964 ; 631-749-3210

Vine Street Cafe