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.

WHAT TO DO:

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.

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.

PERLMAN MUSIC PROGRAM: Take in one of the stunning waterfront free Chamber Music concerts or splurge on tickets to their annual fundraiser, “A Taste of Shelter Island,” at their stunning beachfront campus. Friday, July 26, 2019 www.perlmanmusicprogram.org

SHELTER ISLAND PILATES AND BARRE: Described by Hamptons Magazine as “one of the most coveted exercise classes on the East End, “Shelter Island Pilates & Barre Studios offer world class sessions with former ballerina and choreographer Suzette Smith. Barre Classic
is an open-level ballet-inspired full body workout that incorporates elements of Pilates, dance and functional training. Suzette leads her dedicated class in a fast-paced, rigorous, and low-impact class set to pop music, designed sculpt, slim and stretch the entire body. No dance experience is necessary and beginners are welcome! www.shelterislandpilates.com/barre
@shelterpilatesbarre

PADDLE BOARD RENTAL: Venture Out has a walk-up service is located right on Crescent Beach, also known as Sunset Beach. There is no appointment required and they will get you out on the water immediately. Venture Out also delivers for free to any beach, house or location of your choice with water access on Shelter Island. They also offer guided and unguided creek paddles, group tours, lessons, sunset paddles at Crescent Beach. Call or Text 631-317-7466 to make a reservation, arriving with a large group, or for more information. www.ventureoutsi.com
@ventureoutsi

GOLF: Shelter Island Country Club/Goat Hill is a public course offering 9 holes of golf, a driving range and a bar and restaurant to relax in since 1901. www.shelterislandcountryclub.com

BEACH DAY:  Being that you are on an island, there is sure to be a beach that fits
your sunbathing style. Hit Crescent Beach for a singles scene, Wades Beach for family fun, Shell Beach for easy boat access, or Hay Beach for privacy, just to name a few.

THE SHELTER ISLAND FIREWORKS:A stunning display and island tradition now in its 62nd year, the Shelter Island Fireworks by Grucci, located on Crescent Beach (better snag that coveted Sunset Beach restaurant dinner res now) is a highlight of every Shelter Island summer for residents and visitors. Saturday, July 13, 2019. www.shelterislandfireworks.comJazz

Image via Rams Head Inn

NIGHT AT THE RAM’S HEAD INN: This iconic Inn, now in the 40th season offers Live Jazz every Sunday Night set to the sunsetting over Coecles Harbor. Grab a seat in their classic cocktail lounge, an adirondack on their sprawling lawn, or reserve a table in their fine dining & farm to table restaurant. Every Sunday, Memorial Day – Labor Day. www.theramsheadinn.com @theramsheadinn

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.

WHERE TO EAT:

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. @marieeiffelmarket Psst! Marie Eiffel also has a super chic fashion boutique on the island as well.

VINE DINING: Vine Street Cafe 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

SUNSET COCKTAILS: Grab a bottle of wine and head to Crescent Beach to watch the sunset.
Or head to the bar at Sunset Beach (located on Crescent Beach), order one of their famous mojitos, and relax.

—by Willa O’Connor