A season of holiday cheer!

Holiday cheer at The Chequit Hotel
The Chequit Hotel is all dressed up as a season of holiday cheer gets underway.

The second of two concerts at the school, the PTSA Holiday Boutique, and a Senior Holiday Party at the Community Center are up next as the season of holiday cheer on Shelter Island continues.

To add your event to the list, send an email to editor@shelterislandgazette.com.

Holiday concerts at the school

Students are giving holiday concerts at the school, in the gym this year due to pandemic restrictions. Grades PK to 7 presented their holiday concert last week — you can watch the recording here. Students in Grades 8 to 12 present their holiday concert on Wednesday, December 15 at 7:30 PM. Check the school’s Facebook page for the link to the livestream event.

Senior Holiday Party

The Town Recreation Department welcomes residents age 60+ to join a Senior Holiday Party in the Community Center feauring a pasta lunch and treat from Shelter Island SLICE Restaurant. Sing along to favorite holiday tunes and share in the love and laughter of the season. Thursday, December 16 at noon. Advance registration is required. Contact Bethany at 631-749-0309 or Emily at 631-749-0978. They can also arrange transportation.

PTSA Holiday Boutique

The PTSA of Shelter Island will host its annual Holiday Boutique to allow kids an affordable shopping experience. This year’s venue is Community Center, where the boutique will take place on Friday, December 17, from 9 AM to 4 PM, with designated times for student shopping during school hours. Meantime, you can drop off new and gently used items in good condition in the school lobby until December 16. Wrapping supplies, too. Proceeds support Island families in need.

Community Christmas Dinner

St. Mary’s Episcopal Church will host a Community Christmas Dinner featuring turkey, mashed potatoes, and gravy, with guests bringing a side dish or dessert to share. All are welcome to attend on Saturday, December 25, from 1 to 3 PM. RSVP to Rhonda in the church office at 631-749-0770. Know someone who could use a holiday meal delivery? Volunteers stand ready to deliver meals to homebound seniors. To arrange, contact the Senior Activity Center at 631-749-1059.


Past events

These events have already occurred, but we include them to remind our readers of the rich array of community offerings here on Shelter Island.

Community Thanksgiving meal

The Shelter Island Fire Department hosts this traditional Thanksgiving meal at the Center Firehouse with the Senior Citizens Foundation of Shelter Island and the Shelter Island Lions Club. On Thanksgiving Day, Thursday, November 25, from 2 PM. Enjoy a free, hearty meal of turkey, stuffing, gravy, mashed potatoes, vegetables, and pie cooked by Jamie Cogan. Call the Senior Activity Center at 631-749-1059 to arrange a ride (or have a meal delivered if you’re homebound).

The Chequit holiday lights

Our friends at The Chequit will light up the historic inn with a festive display. There will be complimentary light fare and drinks passed around, including hot chocolate and donuts. Enjoy carolers and a visit from Santa. Friday, November 26, from 4 to 6 PM.

St. Nicholas Fair

The Episcopal Women of St. Mary’s Episcopal Church host the beloved St. Nicholas Fair, including the famous cookie walk where you can fill a tin with home-baked holiday cookies. Local artisans and vendors will be selling gift items at booths set up inside Parish Hall and out on the lawn. No café this year, but homemade soups will be available — Saturday, December 4, from 9 AM to 3 PM.

Chamber of Commerce tree lighting

The Shelter Island Chamber of Commerce hosts its annual tree lighting with a gathering on the steps of Shelter Island Police Department headquarters. Join with friends and neighbors to sing songs as the Town rings in the holiday season. Then head over to the Community Center for a treat and a chance for kids to meet Santa. Tuesday, December 7 at 5 PM.

Sylvester Manor Windmill Lighting

Sylvester Manor hosts its first Windmill Lighting on Friday, December 10 at 4 PM. The event features cocoa, cookies, and carols at Windmill Field, 21 Manwaring Road. No RSVP is necessary. Dress warmly!

Santa & Mrs. Claus at the History Center

Santa & Mrs. Claus visit the Shelter Island History Center to share some holiday cheer. Kids are welcome to drop by on Saturday, December 11, between 11 AM and 2 PM to meet with the jolly couple and receive a unique holiday gift.