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Shelter Island – A Uniquely Beautiful Place


Shelter Island, an 8,000-acre island situated between the North and South Forks, is surrounded by Shelter Island Sound on three sides and Gardiners Bay on the fourth side. In 1980, The Nature Conservancy preserved nearly 1/3 of it, known as Mashomack Preserve. Originally inhabited by the Manhansett Indians, English settlers arrived in 1652. Easily accessible by car ferry from Greenport on the North Fork and from North Haven on the South Fork, it is a uniquely beautiful place.

In 1652, Englishman Nathaniel Sylvester, one of four Barbados sugar merchants, officially purchased Shelter Island from the chief of the Manhansett tribe. He then constructed a house on the island for his 17-year-old bride. In 1673 Sylvester claimed sole ownership of Shelter Island. The Sylvester estate was developed as a large provisioning plantation using enslaved Africans, Native Americans, and English indentured servants. Sylvester and his associates were involved in the Triangle Trade between the American colonies (including the Caribbean), Africa and England. Maura Doyle, Historic Preservation Coordinator of Sylvester Manor remarks, “An estimated 200 enslaved Africans, indentured Manhansett Indians and freed African-Americans are buried at the Burying Ground on the property. The Sylvesters gave shelter to many persecuted Quakers and a Quaker Cemetery is also located there.”

Sylvester Manor is currently embarking on a new era as an organic farm, historic plantation and vibrant arts and education center. Along with a very successful CSA program, they have school field trips and events including a reading of Seedtime, by author, poet, and farmer Scott Chaskey on March 21. Their House Concert Series begins with a sold out Bluegrass House Concert featuring Sierra Hull & Courtney Hartman on March 22. Their Annual Farm to Table Dinner Benefit is on June 28. 

Nanette Lawrenson, Executive Director of The Shelter Island Historical Society, founded in 1922 by Alice and Andrew Fiske, states “SIHS owns and operates the Island’s only museum, the Havens House Museum, built in 1743 by James Havens.” It was placed on the State Register of Historic Places and the National Register of Historic Places in 1986. SIHS has an archival vault with at least 11,000 documents making it a destination for writers and researchers. Their exhibit, “Race & Ethnicity on Shelter Island 1652-2000” runs through March 22. Their signature annual fundraiser “Black & White Benefit,” an elegant outdoor party with dinner by noah’s, is on July 19.

Linda McCarthy of Daniel Gale Sotheby’s International Realty has been living full-time on Shelter Island for 13 years. She observes, “Shelter Island has a quiet, small town rural feeling where you can get away from it all.” She remarks, “The real estate market is very strong right now and inventory is down. Waterfront is always hot at any price, especially navigable water and vacant land is moving again.” There are many attractions on Shelter Island from boating, golfing and biking to the many beautiful beaches. Crescent Beach and Wades Beach have facilities and lifeguards, Menhaden Lane Beach overlooks Gardiners Island and Bug Light, while Shell Beach lies on a curved peninsula jutting out into West Neck Harbor and Shelter Island Sound. There are numerous summer camps for kids, including Camp Quinipet, a sleepaway camp with sailing and Itzhak Perlman’s Music Camp with free concerts throughout the summer. There are many fine restaurants from Vine Street Café, 18 Bay, Ram’s Head Inn, Sunset Beach and Pridwin Hotel to La Maison Blanche, Sweet Tomato’s, Salt Waterfront Bar & Grill, Bob’s Fishmarket, and Dory Waterfront Restaurant. Linda reflects, “With beautiful beaches, fine dining, exciting events, and great activities, you have everything you need right here. Easily accessed from both Forks, it is the best of both worlds.”

Margaret Colligan of Daniel Gale Sotheby’s International Realty, a full-time resident of Shelter Island for seven years, describes Shelter Island as “a throw back to a kinder, gentler time.” She notes, “The real estate market is quite enthusiastic and moving nicely. Waterfront is very attractive with an eclectic range of creeks, ponds, bays, and inlets.” She exclaims, “Shell Beach is a pristine beach where you can bathe on both sides of the peninsula and dock your boat on the harborside. Menhaden Lane Beach in Hay Beach has gorgeous vistas of the Sound, and Crescent Beach is a fun beach with music and dining.” There are many events in the summer, including the Chamber of Commerce’s Annual Fireworks Display at Crescent Beach on July 12 and the 51st Annual Art Show & Craft Fair on August 23. Enjoy kayaking on the scenic inlets or visit Mashomack Preserve and go hiking or birdwatching. Margaret observes, “Shelter Island is more bucolic than the North and South Forks and is an entity unto itself.”

Georgiana B. Ketcham, an independent real estate broker on Shelter Island for over 45 years, reflects, “Shelter Island is and always will be a vacation paradise, as we have become a weekend retreat for many second home owners. It will always be a permanent home for 5th and 6th generation Shelter Islanders.” Her motto is, “There is no place in the world where you can be so well-entertained for free as you can on Shelter Island. Just visit Bridge Street, Crescent Beach, or listen to the music from the Perlman Music Camp during the summer!”

Shelter Island is a haven for nature lovers, beachgoers, and boating enthusiasts alike, as well as those who seek a quiet, peaceful lifestyle. A hidden gem surrounded by water, Shelter Island is a delightful retreat.

Ruth Thomas, a freelance writer on the East End enjoys history, music, literature, art, nature, the beach, and her cute dachshund, Clancy. She can be contacted at [email protected]