Featured Story

The Season of Lights is upon us: Island holiday events to ring in good cheer

This week will usher in the Christmas season on the Island with beloved traditions. Accompanied by caroling, the Island’s Christmas Tree will be lit on Tuesday, Dec. 2 at 5:30 p.m. at the Police Department Headquarters, courtesy of the Shelter Island Chamber of Commerce. Afterwards, everyone is invited to walk over to the Community Center to warm up with hot chocolate and cookies, and have children’s photos taken with Santa Claus. Admission is free. All are welcome.

The Island’s agricultural tradition takes center stage on Friday, Dec. 5 at 4 p.m. with the lighting of the 1810 Dominy Windmill at Sylvester Manor Educational Farm.  All are welcome to enjoy refreshments and caroling at this free event, at the Windmill Field, 21 Manwaring Rd.

The annual St. Nicholas Fair returns to St. Mary’s Church on Saturday, Dec. 6 from 9 a.m. to 2 p.m. The event offers great shopping for Christmas gifts and decorations, many handmade by Island crafters. Bid on special items in the Silent Auction. Soups and sandwiches will be sold.  

The Cookie Walk is a favorite feature of the fair; fill a coffee can with homemade cookies to bring home the taste of the holidays.