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Stepping Back on Shelter Island

Posted on 31 July 2008


by Catherine McNamarra

Fans of classic East End houses will have the opportunity to take a peek at several restored homes this weekend. On Saturday, August 2 from 1 to 5 p.m., the Shelter Island Historical Society invites visitors to attend the Shelter Island House Tour.

The tour features five historic houses and a windmill from 1810 that can be visited in any order. The houses have been slightly updated but maintain many of their original details. Dating from the time when Shelter Island was centered around farming and maritime activities, the Nathan Dickerson 1857 farmhouse, known at that time as the “House of Lords” for the local government issues discussed there, is one of the three farmhouses included in the tour. Built between 1750 and 1800, the Cartwright Farmhouse, named after Sag Harbor whaling captain Billy Cartwright, showcases many historic maps and photographs from the period. The Gingerbread House, known to anyone who has traveled the island’s ferry route, is set in Shelter Island Heights. Originally a mid-18th century farmhouse, the gingerbread and tower were built onto the house to adapt to the style of the summer cottages in the area.

Highlighting the tour are the old Windmill on Manwaring Road and the home of Meddi and Alan Shaw. The windmill was built in Southold in 1810 and was later moved by barge to Shelter Island in 1840. Used by Joseph Congdon to replace an old gristmill, it was last in operation in World War I, providing meal and flour to the community. Those who visit the windmill between 1 and 3 p.m. will meet Bob Hefner of East Hampton, a world-renowned expert on windmills. Visitors will receive a book on the windmill’s history. One of the youngest homes on the tour, the Shaw home will host afternoon tea and snacks for visitors. The house, once though to be haunted, has a mysterious, but enchanting history about a man with a lost love and his Steinway grand piano.

Hill Crest Cottage, a typical Shelter Island Heights house from the late 19th century, will also be visited during the tour. Originally owned by Brooklyn railroad executive Lynde Catlin, the cottage housed his large family for more than 40 years.

The tour will begin at the headquarters of the Shelter Island Historical Society, Havens House, 16 South Ferry Road, Shelter Island, at 1 p.m. To purchase tickets in advance, send $30 to the Shelter Island Historical Society (tax deductible) at P.O. Box 847, Shelter Island, NY 11964. Tickets are available at the door for $40. For more information, call 749-0025. 


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