Season of holiday cheer starts this week!

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

A Community Thanksgiving meal kicks off a season of holiday cheer that includes festive lighting at the nearly-completed Chequit Hotel, the St. Nicholas Fair at St. Mary’s Episcopal Church, and the Chamber of Commerce traditional tree lighting in the Town Center.

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

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.

Holiday concerts at the school

Students will give holiday concerts at the school, in the gym this year due to pandemic restrictions. Grades PK to 7 present their holiday concert on Wednesday, December 8 at 6 PM; students in Grades 8 to 12 present their holiday concert on Wednesday, December 15 at 7:30 PM.

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.

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 8 AM to 4 PM, with designated times for student shopping TBA. Meantime, you can drop off gently used items in good condition in the school lobby until December 17 (note: the PTSA cannot accept donations of stuffed animals). 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. Saturday, December 25, from 1 to 3 PM. 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.