Winter and the holiday season are a wonderful time of year! But sometimes there’s so much going on, that it becomes overwhelming to plan this special time with our families! That is why Greenwich Moms has organized all the best activities in Greenwich and the surrounding areas into one, easy to follow guide! This year we have also included a list of all of our favorite holiday shopping boutiques. We are excited to present the 2024 GREENWICH MOMS HOLIDAY GUIDE – Your one stop guide to the best winter activities in the area for you and the whole family.

While we scour the calendars of all of our beloved local organizations, read the local publications, and try to anticipate all of the events happening, we don’t catch them all! If we missed a great holiday event in town, please email us at [email protected] and if appropriate we will add it! 

HOLIDAY BOUTIQUES IN GREENWICH

Holiday Sip & Shop at Abilis Gardens & Gifts
December 4 @ 5:00 pm – 8:00 pm

Greenwich Arts Council Holiday Bazaar
December 7 @ 12pm – 6pm
299 Greenwich Avenue

Greenwich Historical Society – Holiday Boutique
December 4 @ 5:30 pm – 8:00 pm
December 5 @ 9:30 am – 4:30 pm

HOLIDAY TRAIN SHOWS

HOLIDAY ACTIVITIES IN GREENWICH

Kick off the holidays with us!
🍪A cookie swap (please bring 2 dozen of your favorite cookies- no nuts, please!)
🎨Fun crafts for the kids @makemodernstudio
📕Story time with a special guest!
🎶A cappella carols @greenwichacappella
🎁Gift shopping with @food52
🍫Make-your-own hot chocolate bar @onthemarcevents
And more!

Greenwich Moms, in partnership with @food52, invites you to make merry at our HOLIDAY FAMILY FETE on Saturday, December 7 from 11 a.m. to 2 p.m.

December 7 | 11am – 2pm 
Arch Street Teen Center
Purchase Your Tickets!

Santa and his three LIVE reindeer return to Greenwich for the 16th Annual Greenwich Reindeer Festival & Santa’s Workshop presented by Jenny Allen at Compass Real Estate, the “North Pole on North Street,” Sam Bridge Nursery & Greenhouses, 437 North Street, Greenwich, Connecticut, from November 29 to December 24, 2024. The cherished town tradition continues for the sixteenth consecutive year at this expansive nursery where visitors can have their photo taken with Santa, meet the reindeer and also enjoy Santa’s Workshop sponsored by Greenwich Pediatric Dental Group, which provides more space for families.  Guests can enjoy the “Reindeer Coloring Station” sponsored by Jenny Allen at Compass and “Letter Writing to Santa Station” sponsored by Greenwich Pediatric Dental Group,” while waiting in line for their photo with Santa.  A portion of all photos with Santa will be donated to Kids In Crisis, a non-profit organization based in Greenwich, but serves all of Connecticut. A Kids In Crisis Giving Tree will also be available for people to support their important mission. We’re excited to welcome the new Reindeer Stable Sponsor, Greenwich Braces. This all takes place just minutes from downtown Greenwich. Parking is free. Children, adults, and all dogs (on leashes) can have their photo taken with Santa at Santa’s Workshop. PLEASE BRING YOUR DOG FOR PHOTOS WITH SANTA ANYTIME WE’RE OPEN, but for an added incentive to visit Santa with your dog when the lines aren’t as long as Saturday, you’ll receive a Doggy Gift Bag sponsored by Cornell University Veterinary Specialists every Monday – Friday throughout the event. 

November 29 – December 24, 2024
Visit LIVE REINDEER and PHOTOS WITH SANTA
Monday – Friday 12pm – 6pm, Saturday 9am – 6pm
Sam Bridge Nursery & Greenhouses
437 North Street, Greenwich, CT 06830
www.GreenwichReindeerFestival.com

Enter a winter wonderland in the Historical Society’s Museum Lobby, filled with gloriously decorated trees that can be bid on via a silent auction. Local organizations, including upscale retailers, garden centers and designers hand craft and decorate the trees in their unique style. Celebrate their talents for making homes festive sanctuaries during the holidays and join the bidding. Trees are picked up at the end of the Festival on December 7.

Place a bid in our sixth annual Festival of Tabletop Trees.

Creatively decorated by local retailers, organizations and designers, these wonderful trees can be viewed, purchased or bid on via on-site silent auction. Winners will be announced at the end of the festival. Celebrate the talents of those who help us make our homes festive sanctuaries during the holiday season.

December 4 – 6 9:00am – 5:00 pm
December 7 11:00am – 7:00pm
Greenwich Historical Society
https://greenwichhistory.org/ghs-events/

Santa and Friends Arriving in Greenwich for Annual Tree Lighting on December 6

December 6
4pm – 5pm 
Greenwich Town Hall

Old Greenwich Merchants Association present First Light, an annual, magical event that closes Sound Beach and invites residents to come together and stroll. Lights, Entertainment & Santa! Bring the family! The intention of the event is to showcase local businesses, and merchants are encouraged to invite people in to celebrate the season.

First Light 2024 includes: Antique Fire Truck 🚒rides, Santa🎅🏻, music, entertainment, holiday lights and trees🌲 , snacks and treats for young and old. The best Holiday Party in town and FREE! See you on Saturday, December 7 from 5:00 PM – 8:00 PM in Old Greenwich! ❄️

December 7
5:00pm-8:00pm
Sound Beach Avenue, Old Greenwich
More Details

Brace yourself for some unbridled Christmas-season excitement, as the Byram Shubert Library hosts their annual Holiday Tree Lighting! It will be a heartwarming evening filled with music, fun, and festive spirit for all ages. 

The highlight of the event is a live performance by the country music band GUNSMOKE, whose rich history of entertaining audiences with classic country, Western swing, and rockabilly hits spans over 25 years. Whether you’re a long-time fan of twangy tunes or just looking for some toe-tapping fun, Gunsmoke is sure to deliver an unforgettable show.

Family-Friendly Festivities: Beyond the music, this event offers something for everyone:

• School Choirs and Crafts: Enjoy performances from local student choirs and create festive crafts.
• Surprise Guest Appearance: Have your photo taken with a very special guest (hint: we’re expecting he’s got a red suit and a beard!).
• Refreshments: Sip on seasonal favorites and enjoy delicious treats as you bask in the glow of the holiday tree.

December 7
4:00pm-6:00pm
Byram Shubert Lbrary

Celebrate the holidays at the Greenwich Historical Society’s Holiday Festival! Bring your entire family for photos with Santa in the Historic Barn, complete with gingerbread decorating and crafts in Santa’s workshop!

In our Museum Lobby, admire the festive wonderland that is our Festival of Trees, featuring community-crafted trees by local designers, merchants, nonprofit organizations and garden clubs. Choose your favorite of the trees and bid in the silent auction to take it home!

Take part in the holiday cheer and enjoy a winter beverage while listening to performances by the Connecticut Yuletide Carolers. Enjoy grilled cheese and tomato soup from Melt Mobile, delicious sweet treats and explore our beautiful illuminated grounds. Warm up outside by the fire with some s’mores and hot cocoa to round out an evening of holiday fun!

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December 7, 4pm – 7pm
Greenwich Historical Society
Learn More

🎄 Whether you’re more into the “après” or the ski, all are welcome to our cozy chalet, featuring a winter wonderland of displays and a magical holiday market!

🍷There’ll be marshmallows for toasting and festive drinks like hot cider (or Cabernet!) to enjoy while you begin your holiday shopping.

🎁 We’ve got a special something for everyone on your list including our handmade @elvesandco wreaths, beautiful fresh-cut trees and collectible ornaments, décor & candles.

☃️ Plus, your little snow bunnies can enjoy family-friendly activities like a snowy scavenger hunt, a DIY cocoa station, s’mores n’more!

🚠 So take the bunny slope (or the gondola!) down to 201 Pemberwick Road on Saturday, December 7th to join in the festivities!

See you off the slopes!! ❄️

December 7
12:00pm-6:00pm
201 Pemberwick Road, Greenwich
Arch in Bloom

Come celebrate the holidays with us at our annual cookie social! Bake or bring your favorite cookies to share your sweet treats—though bringing a treat is not required to join the festivities. Coffee will be served. Free and open to the community!

All YMCA members and guests are invited to celebrate the holidays at the Y. Come and join the fun! Bake or bring your favorite cookies to share your sweet treats—though bringing a treat is not required to join the festivities. Coffee will be served.

December 13 | 9:00am – 10:00am
YMCA Greenwich

Decorate a Gingerbread House at 2CC!

Registration Required, $35/house 
Limited Spaces Available

Children under the age of 12 need to accompanied by an adult.

Email [email protected] for more information! 

December 14
10:00am – 12:00pm
Email [email protected] for more information

Register at https://ccfpp.org/operation-santa/

GEMS is bringing the Holiday Season to you and your family this year! With the overwhelming response from the GEMS Halloween Haunt and the community, Greenwich EMS brings a decorated ambulance to the Holiday Season. The decorated ambulance and staff will make your holiday season this year memorable for everyone.

Please drop off your wrapped gift(s) for your child, and the Holiday Express will deliver them to you and your family!

Register today to reserve a visit from the Holiday Express! Space is limited.

December 13,14, 20, 21
4:00pm-8:00pm
More Details

Saturday December 14th from 1-3pm – join us for ice cream at Cups N’ Cones with Santa to see if you made the nice list!

December 14
1:00pm – 3:00pm
Cups N’ Cones

The first ever community wide Chanukah celebration in Old Greenwich.

• Entertainment – Children & Adults
• The OG Menorah Rise – Building the OG Menorah
• Chanukah Land – Food Stations, Art & Crafts, fireman presentation & Adult station

Hosted by the Greenwich Fire department & Sound Beach Volunteer Department

Sunday, December 15
1:00pm – 3:00pm
The Old Greenwich Fire Station

Teddy Bear Story House with Jenny at Coffee for Good! Roll out of bed and join us in your PJS. Special guest for this story hour will be Mrs. Claus!

The event is free. 

December 21
8:00am at Coffee for Good
Email [email protected] for more information

Pre-movie Activities 

• Holiday music & PJ party
• Holiday photo opportunities
• Holiday art & craft
• Snacks and Hot chocolate bar

Wear your Holiday pajamas and bring your blankets! Advanced reservations/tickets required; space is limited.   $12 per person 

Complete Registration Information (PDF)

Saturday, December 21, 2024 | 5pm (Movie starts at 6pm) 
Bendheim Western Greenwich Civic Center
Buy Tickets at https://www.greenwichct.gov/webtrac

Celebrate Chanukah with Chabad of Greenwich! Join us for a night of festivities, complete with a Grand Menorah Lighting and a Chanukah Concert.

January 1
6:15 Lighting, 7:30pm Concert
Register at chabadgreenwich.org/

Dorothy Hamill is a Town-owned ice rink that is open from early September through mid-March. The Rink offers a variety of ice skating activities and programs for all ages.

Dorothy Hamill Skating Rink, Sue Merz Way, Greenwich
More Details

HOLIDAY EVENTS NEARBY

Holiday Wish Express offers 20,000 square feet of enchanting, immersive holiday experiences for the whole family! New England’s largest indoor Christmas event opens on Saturday, November 23, and runs on select dates through Christmas Eve!

November 23 – December 24 (on select dates)
Stamford Town Center (above Barnes and Noble)
www.theholidaywish.com
Tickets from $35.00 (Adults) and $25.00 (Children).
For group arrangements and private events, reach out to [email protected]

This year, NYC’s family-favorite holiday tradition, Bronx Zoo Holiday Lights, will feature even more lights and new lantern displays! Walk through a winter wonderland filled with nearly 400 lanterns, immersive light shows, 6 safari lantern trails, and the all new Enchanted Sea. Plus enjoy ice-carving demonstrations, illuminated performers, seasonal treats, classic holiday music, and so much more.

Spend quality time with loved ones this season at the beloved Bronx Zoo Holiday Lights.

Reserve Tickets Now at BronxZoo.com

November 22, 2024 — January 5, 2025
Bronx Zoo, 2300 Southern Boulevard, Bronx, NY
https://bronxzoo.com/holiday-lights

Nov 22 – Dec 30 | 4:30pm – 8:30pm
*Open 5pm-8:30pm 11/22-24, 11/27, 11/29, 11/30, 12/1*

Harvest Moon, 130 Hardscrabble Road, North Salem, NY 10560
More Info

⭐ Westchester’s Winter Wonderland is back, brighter than ever! Embark on a 1.2-mile drive-thru adventure filled with thousands of colorful lights, beloved holiday characters, and breathtaking displays. Get ready to light up your holiday season—all from the cozy comfort of your car!

🌟 Proceeds directly benefit the Westchester Parks Foundation who work to to keep Westchester County Parks beautiful, open, and accessible to all who need them

🎁 Gift memories to someone special! Purchase a gift card for Westchester’s Winter Wonderland 2024 here

November 30 – December 31
Kensico Dam Plaza, 1 Bronx River Pkwy, Valhalla, NY
Get You Tickets Here! 

The fourth annual Holiday Stroll with Dan Woog’s “06880.“ This year’s event will feature participating retailers and restaurants offering deals and promotions, activities for children (face painting, s’mores, Santa photos, and more), and performances by the Staples High School Orphenians on Upper Main Street, Lower Main Street, corner of Post and Main outside Anthropologie, and Sconset Square. The Elm & Main complex at 136 Main Street will serve as the headquarters of Holiday Stroll with Santa, a DJ, a photo booth, and much more.

The Holiday Winter Market on Elm Street (Sigrid Schultz parking lot) will feature a variety of vendors for your shopping pleasure. (See participating vendors below). The Westport Police Department will host a toy drive, so please bring a new toy.

Saturday, December 
5:00pm – 7:00pm 
More Info

December 
Larchmont, NY
More Details

Shark-Diving Santa  Santa Claus will be diving with sand tiger sharks in the Aquarium’s “Ocean Beyond the Sound” during the month of December. See Santa dive on most Saturdays and Sundays December 1 – 29 at 10:30 a.m. and 12:30 p.m. This experience is free with Aquarium admission.

“Rudolph the Red-Nosed Reindeer 4D Experience”  – Playing through January 2! Rudolph the Red-Nosed Reindeer shines in an all-new 4D Experience at the Aquarium this holiday season! This 10-minute adaptation of the film uses the same stop-motion animation as the beloved television classic to deliver a visually brilliant experience true to the story that has charmed audiences for generations. Join him on his epic adventure to save Christmas now through January 2! Tickets for a 4D movie are $7 per person ($6 for Aquarium members). Aquarium admission is optional. Click Here for Tickets

Elf Power VR Experience: Discover the true meaning of Christmas as you fly by snow-capped mountains in Santa’s jet-powered sleigh in search of a child who needs to believe again. And the magic doesn’t end there – you never know who you’ll meet, thanks to your Elf Power!

Flurry Zone – An Indoor Snow Experience: No matter the weather outside, we are guaranteeing a snowy forecast inside every day in December, thanks to a special snow machine that will produce a fun flurry on the hour every day! “Flurry Zone! An Indoor Snow Experience” will produce a squall every hour on the hour, from 10 a.m. to 4 p.m., in Newman’s Own Hall. The snowfall will last for 5 minutes but, through unique technology, evaporates as it hits the floor, so no shoveling will be required. This experience is free with Aquarium admission. Click Here for Tickets

New Year’s Eve Celebration: Join us on December 31 from 10 a.m. to 1 p.m. for our “Noon Year’s Eve” celebration – perfect for families with young children who want to celebrate the end of 2024 together, but not at the stroke of midnight. Don’t miss family-friendly activities including face painting, a fun craft, music, and of course a countdown to 12 o’clock noon! This celebration is free with Aquarium Admission. Click Here for Tickets

Events through January 2, 2025
Maritime Aquarium, 10 N Water St, Norwalk, CT 06854
https://www.maritimeaquarium.org/

“This holiday production puts a new spin on Christmas classics.” The New York Times

Every December for the past 30+ years, arranger, composer, producer, director, and musician extraordinaire Rob Mathes has been ringing in the holiday season with a spectacular celebration that features Mathes, his all-star band, and a chorus of saints and friends.

This year’s lineup will include long-time Mathes friend Ian Cron, joining the amazing vocalists James “D-Train” Williams and Vaneese Thomas. New this year is a string quartet, with the incomparable Jonathan Dinklage on violin, Erin Benim-Mayland on violin, Yuko Naito on viola, and Adele Stein on cello.

This high-energy evening of rock, jazz, and blues — original tunes and new spins on your favorite holiday classics — is a local holiday tradition not to be missed!

Rob Mathes has worked with virtually every big name in the music industry, arranging, producing, directing, recording, and performing with the likes of Bono, Bennett, Sting, and Springsteen. But despite his busy schedule, he makes time for his fans, and it’s always a treat to have this Greenwich, CT, native “home” for the holidays.

The Rob Mathes Holiday Concerts support Food Rescue US – Fairfield County
Be the Rescue. Fight Hunger. Help the Planet.
Learn more at: foodrescue.us

December 20, 21 at 8:00 pm
December 22, at 3:00 pm
The Performing Arts Center at Purchase College
Purchase Tickets

HAPPY HOLIDAYS FROM GREENWICH MOMS!