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The Five-Point Weekend Escape Plan

Escape the Hamptons on Shelter Island

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5. Oddball Day


Historic Sylvester Manor hosts a variety of cultural events throughout the year.  

Take a break from all the physical activity to experience the island at the leisurely pace of a resident. Grab coffee and a breakfast burrito at local favorite Stars Cafe and then drive (you can bring a car over on the ferry) to former seventeenth-century plantation Sylvester Manor (be sure to confirm that they have open hours that day; free admission), which has remained in the Sylvester family for eleven generations. Stroll the well-maintained grounds and explore the original manor house and on-site organic farm that supplies local restaurants. (Check the calendar for events including upcoming performances of Shakespeare’s Much Ado About Nothing, the annual Contra Dance, and en plein air painting or banjo building workshops.) Stop by the Manor’s farmstand (open daily) to buy picnic supplies including fresh chèvre from Catapano Dairy and a loaf of bread from Blue Duck Bakery. (For more robust picnic fare, stop by Vine Street Café Market for hand-cut potato chips and turkey meatloaf.) Next, bring your lunch and a fishing rod out to Hay Beach by Menhaden Lane, where islanders go to catch bluefish. Afterward, head to secluded Fresh Pond, a freshwater pond at the end of Fresh Pond Road, were locals like to cool off. In the evening, make your way to the Perlman Music Program, a summer camp run by violinist Itzhak Perlman, and catch one of their free Works in Progress concerts or an alumni recital ($20) on Friday and Saturday nights in the summer. Finish up the day by walking down the shore to Sunset Beach Restaurant for a late dinner of French cuisine and a glass of wine under the stars.


Published on Jul 18, 2013 as a web exclusive.

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