December Events In Greenwich

Krissy Blake | December 1, 2025

December Events in Greenwich

'Tis the season! There are so many festive activities around town this time of year. Here are some to enjoy! Wishing you a joyful holiday season.

Nov 28–Dec 24 – Greenwich Reindeer Festival & Santa’s Workshop
Sam Bridge Nursery & Greenhouses, 437 North Street

Live reindeer, photos with Santa, kids’ coloring + letter-writing to Santa, raffle, “Name the Baby Reindeer” contest.
Benefits Kids in Crisis, with a Giving Tree on-site

Hours:

Late Nov–Dec – “Let There Be Lights” on Greenwich Ave & Cos Cob

Trees on Greenwich Avenue and in the business district are wrapped in lights, usually lit from Thanksgiving weekend through the season—great for evening strolls and shopping.

Pancake Breakfast with Santa – Boys & Girls Club

Family Wreath-Making Workshop – Greenwich Botanical Center

Byram Shubert Library Holiday Tree Lighting

First Light Old Greenwich – Sound Beach Ave

5–8 pm
Street closed to cars; lights, entertainment, Santa, treats, and local shops open — very family-friendly.

Arch in Bloom “Flurry Fest” – 201 Pemberwick Road

12–6 pm
Trees, wreaths, holiday market, cocoa station, kids’ scavenger hunt, Santa visit.

GEMS Holiday Express – Nighttime Santa Ambulance Rides Begin

Dec 12, 13, 19, 20 • 4–8 pm
Get ready for a unique holiday experience with Holiday Express, where Santa and his festive crew arrive in a fully lit, winter-themed ambulance to bring joy and gifts directly to your doorstep! Since its inception, Holiday Express has been a highlight of the season, creating unforgettable memories for families across Greenwich. Santa himself delivers a pre-selected, parent-provided gift to each child, making it a personal and magical moment they’ll never forget.
Register here

Greenwich Historical Society Holiday Festival – “A Night at the Museum”

4–7 pm • Greenwich Historical Society
PJs encouraged; crafts, decorate gingerbread people, photos with a guest from the North Pole, treats, fireside cocoa. Rain date Dec 14
Register here

Winterfest – Cos Cob Library

1–3 pm
Arts & crafts show, hot cocoa, music, gingerbread house contest, Toys for Tots drop-off.

Operation Santa – Cos Cob Fire Police Patrol

Dec 13, 14, 20, 21 (+ possible Christmas Eve/Day by arrangement)
Cos Cob Fire Police Patrol Benefit set out to spread some holiday cheer with Operation Santa. With a direct donation, Santa along with the Cos Cob Fire Police Volunteers delivered Christmas gifts on the fire truck with a surprise appearance of The Grinch. Families and kids of all ages enjoyed the experience of seeing Santa arrive with gifts on our firetruck. Register here