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Photo by Beverlea Walz | Harrison Weslek negotiating with Santa at the PTSA Breakfast with Santa.

Holidays on “The Rock” include some of our favorite events and activities of the entire year. Starting the weekend after Thanksgiving, our quiet island revs up. Come on over for festive fun and maybe even some snow.

Winter? Who says it’s winter? Not the Friends of the Library who sponsor the annual Turkey Plunge at Crescent Beach on the Saturday after Thanksgiving, Nov. 30. The intrepid bathers raise money for the Shelter Island Library by collecting pledges from sponsors. They go into the frigid water to their ankles, knees or all the way. There are prizes for the best costumes and most money raised but, after last year, no prize for who stays in the longest because two people, determined to win, wouldn’t leave the water! It’s great fun to watch—smiles abound as people dash in and out of the chilly water—and this community event usually wraps up quickly.

Also on Nov. 30, the ladies of the Shelter Island Presbyterian Church host their Sugar Plum Fair, with handmade crafts, lots of baked goods and a luncheon. Santa even makes an early appearance.

On Dec. 4, the huge tree in front of the police station is lit to glow throughout the holiday season. Sponsored by the Chamber of Commerce, Santa leads the singing of Christmas carols and then everyone heads over to the American Legion for hot chocolate, cookies and a visit with the big, jolly man himself.

Photo by Beverlea Walz | The season of light beams out brilliantly to a December dusk at the Historical Society’s Havens House Barn.
Photo by Beverlea Walz | The season of light beams out brilliantly to a December dusk at the Historical Society’s Havens House Barn.

On Dec. 7, the ladies of St. Mary’s Episcopal Church open their doors for the St. Nicholas Fair. There’s a raffle, lunch and their famous “Cookie Walk,” where you fill a coffee can full of your favorite homemade cookies.

Volunteers and supporters of Sylvester Manor are warmly invited for Tea & Tree, their annual holiday open house, on Saturday, Dec. 7. Enjoy live music, cookies, finger sandwiches and merry-making along with their traditional yet eclectic tea service in the historic rooms of the Manor House. Sylvester Manor Educational Farm continues this tradition of hospitality started by Andrew and
Alice Fiske in 1952.

After that, also on Dec. 7, head on over to the library for their 2nd annual holiday craft fair, featuring locally made crafts and gifts.

Stop by the Shelter Island Historical Society’s Holiday Open House on Sunday, December 8 from 1 to 4 p.m. Santa will be visiting Havens House, decorated by Kathy Dinkel, while children of all ages will enjoy a holiday family event in the barn, including a Shelter Island Student Art Show and hands-on holiday craft activities. Santa will arrive at Havens House at 1 p.m. Volunteers will be available to greet and help shoppers choose from the wide selection of locally made items and find the perfect gift for hostess, chef, reader, equestrian or golfer. Patricia Shillingburg will be available to sign copies of her latest book, “The Nicolls of Sachem’s Neck.” Saunter over to the barn and view the Student Art Show and create your own unique holiday decorations, garlands, ornaments or note cards. Members of ArtSI will judge the students’ work and present awards at 2 p.m. There will be cookies baked by the Island’s best chefs and punch served from a vintage bowl at Havens House while you shop. Popcorn from the popcorn machine, sweets, hot chocolate and cider will be available in the barn, along with caroling with the Girl Scouts. Celebrate the warmth of the season by donating a pair of mittens or gloves to the mitten tree to be shared with those in need. The event is free. There’s something for everyone at this celebration of the holiday season!

Photo by Beverlea Walz | The Historical Society’s Haven House decorated for Christmas.

Photo by Beverlea Walz | The Historical Society’s Haven House decorated for Christmas.

Shelter Island School’s PTSA sponsors a Breakfast with Santa at the Presbyterian Church on Saturday, Dec. 14, where you can eat your fill of pancakes, scrambled eggs, bacon and sausage. The kids can sit on Santa’s lap, have their picture taken and receive a keepsake photo to take home.

In a much-anticipated holiday ritual, Mashomack Preserve opens its doors Saturday, Dec. 14, for a Holiday Open House at the Manor House. Enjoy mulled cider and eggnog, a holiday buffet, caroling and nature crafts for the kids.

The Shelter Island Presbyterian Church hosts a Community Concert on Sunday, Dec. 15, featuring the Community Chorus, hand bells and special seasonal instrumental music.

The week or so before Christmas, Santa makes another appearance at the Shelter Island Fire Department’s center firehouse. Kids under the age of eight can whisper their secret wishes to Santa and enjoy cookies and hot chocolate.

The PBA sponsors community caroling a couple of days before Christmas. Everyone gathers at the police station and climbs aboard a hay wagon that travels from house to house regaling grateful residents with Christmas carols. This is such a popular event that many Islanders request that the merry carolers stop by their houses.

Join us on “The Rock” and help us ring in the holidays!