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Plunging into the holidays: Favorite Island traditions return

The joyful gatherings with loved ones over hearty Thanksgiving meals are just the beginning of a holiday season on the Island that promises to be as full as ever. After being curtailed or canceled last year over COVID concerns, beloved holiday events are back. Here are the highlights for the next few weeks.


While still undergoing renovations, the Chequit halls will be decked and the tree ready to be lit on Friday, Nov. 26 from 4 to 6 p.m.

There will be complimentary light fare and drinks passed around, including hot chocolate and donuts. Carolers will be in attendance.

To kick off the holiday season, the Fire Department will bring Santa by for a visit on the truck.


The 12th annual Shelter Island Turkey Plunge is on Saturday, Nov. 27, 11 a.m., at Crescent Beach. Rain, snow, or shine! Sponsored by the Friends of the Shelter Island Public Library, the event dares plungers to flirt with frostbite as they make a mad dash into the water.

In costumes, bathing suits or wetsuits, this hardy band raises funds for library programs while bringing back the Island’s great post-Thanksgiving tradition.

There will be hot cider and donuts for plungers and spectators, and additional refreshments for sale for the benefit of the Friends. Visit silibrary.org for information on sponsoring or participating.


Registration is open for the Shelter Island Chamber of Commerce 8th Annual Decorate Your “Door” Contest, from now until Dec. 1. Visit the Chamber’s website to register. Chamber Members are invited to decorate their “storefront” for the month of December in either traditional or whimsical decor for the chance to win a complimentary advertisement on the Chamber’s website for 2022.

Decorations must be installed by Dec. 10. Judging will take place Dec. 13-17, and the winners will be announced the following week through social media and an ad in the Shelter Island Reporter. For more information, please email [email protected].


The Menorah will be lit on Saturday, Dec. 4 at 6:30 p.m. in front of the Shelter Island Police Department. This annual Menorah Lighting is a project of the Center for Jewish Life – Chabad in Sag Harbor. All are welcome. For information, email [email protected] or call 631-938-6202.


The Shelter Island Chamber of Commerce Tree Lighting will take place on Tuesday, Dec. 7, at 5 p.m. The ceremonial lighting of the Town tree in front of the Police Department Headquarters will be accompanied by music and caroling. Then all are invited to walk on down to the American Legion to warm up with hot chocolate and homemade cookies, and have your photo taken with Santa Claus.