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 2025 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! 

DECEMBER HOLIDAY BOUTIQUES IN GREENWICH

Greenwich Academy Holiday Boutique
November 23 @ 11:00 am – 3:00 pm

Holiday Sip & Shop at Abilis Gardens & Gifts
December 3 @ 5:00 pm – 8:00 pm

Greenwich Historical Society – Holiday Boutique
December 3 @ 5:30 pm – 8:00 pm (Opening Night – $25 Entry)
December 4 @ 9:30 am – 4:30 pm

HOLIDAY ACTIVITIES IN GREENWICH

Join us for The Enchanted Forest: North Pole Edition at the Greenwich Botanical Center, Friday & Saturday, November 21–22.

Join us this Friday for the Holiday Tea and end the day in style with shopping, a silent auction, and more at the Sip & Shop Cocktail Party!

Tickets are still available for Family Day:
 Shop the Holiday Boutique for unique gifts
 Sip hot chocolate by the fire
 Give back through our Giving Trees supporting Kids in Crisis & Mothers for Others
 Visit the Children’s Giving Shop and meet Santa himself

November 21 – November 22
Greenwich Botanical Center
Buy Tickets Now!

Santa Claus and his three LIVE reindeer are coming to town, as  they return to Greenwich for the much anticipated 17th Annual Greenwich Reindeer Festival &  Santa’s Workshop presented by Jenny Allen & Kristen Studwell, Compass Real Estate, to the  “North Pole on North Street,” Sam Bridge Nursery & Greenhouses, 437 North Street, Greenwich, Connecticut, from November 28 to December 24, 2025. The cherished town tradition continues for  the seventeenth year at the expansive nursery where visitors and their dogs can have their photo  taken with Santa, meet the reindeer and also enjoy the spacious Santa’s Workshop, which features a  Reindeer Coloring Station sponsored by Jenny Allen & Kristen Studwell, Compass Real Estate, Letter  Writing to Santa Station for children sponsored by Greenwich Pediatric Group, a Raffle for everyone  who has their Photo with Santa to win a Mercedes-Benz Kids Electric Car and a “Name the Baby  Reindeer Contest,” to win a Mercedes-Benz Kids Electric Car, while families wait in line for their photo  with Santa to create special holiday memories. All Raffle Winning Names will be drawn by Santa,  Wednesday, December 24. A portion of all photos with Santa will once again benefit Kids In Crisis, a  non-profit organization based in Greenwich. A Kids In Crisis Giving Tree will also be available for  people to support the important work of Kids In Crisis. The Greenwich Reindeer Festival and Sam  Bridge Nursery are proud to support Kids In Crisis for the seventeenth year. This all takes place just  minutes from downtown Greenwich. Parking is free.  

November 28 – December 24, 2025
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

Place a bid in the seventh annual Festival of Tabletop Trees. Local retailers, organizations, and designers will hand craft and decorate a tree which can be bid on and won at the end of our festival. Celebrate the talents of those who help us make our homes festive sanctuaries during the holiday season.

View, purchase or bid on a tree via on-site silent auction.

Trees will be on display at the Historical Society:
December 3 – 6     9:00am – 5:00 pm
December 6     11:00am – 4:00pm

December 3 – 6 9:00am – 5:00 pm
December 6 11:00am – 4:00pm
Greenwich Historical Society
www.greenwichhistory.org

Santa and Friends Arriving in Greenwich for the Annual Tree Lighting on December 5

December 5
4:15pm – 5:15pm 
Greenwich Town Hall

Boys & Girls Club of Greenwich will host its Annual Pancake Breakfast with Santa on Saturday, December 6 from 8:00-11:00am at 4 Horseneck Lane, Greenwich.

All of Greenwich is invited to this festive event.

Click here to purchase tickets.

December 6
8:00am – 11:00am 
More Information

Bring the whole family and learn how to decorate a beautiful wreath using natural and enhanced decorations such as seed pods, pinecones, luxe ribbon, dried berries, and more! Take home a festive wreath to bring holiday cheer to your own front door!

Pricing based on number of wreaths and sizes to be selected upon registration.

Saturday, December 6, 2025 |12-2PM
Greenwich Botanical Center Horticulture Building
Register Here

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 2025 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 6 from 5:00 PM – 8:00 PM in Old Greenwich! ❄️

December 6
5:00pm-8:00pm
Sound Beach Avenue, Old Greenwich
More Details

Join this annual celebration that brings together the Friends of the Byram Shubert Library and the entire Byram community including school choirs. Come and join us for musical entertainment provided by the sensational country music band GUNSMOKE. Have your picture taken with a special surprise guest. Enjoy refreshments and crafts for children.

Sponsored by the Friends of the Byram Shubert Library.

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

🎼On the 6th day of December, Arch in Bloom is gifting you… our sixth annual Flurry Fest! 🎶

❄️ Come walkin’ through our winter wonderland of festive displays and bring the magic home with one of our beautiful, fresh-cut trees!

🍷Have a cup of cheer and enjoy delicious goodies while you peruse our holiday market.

🎁 Made the nice list? Treat yourself or a loved one to a handmade wreath and one of our collectible ornaments or candles.

🚂 Your tiny toys are invited to enjoy a cozy cocoa station, a snowy scavenger hunt, and perhaps even a surprise visit from Santa himself! 🎅🏻

🛷 So, make your shopping list, check it twice, and dash on over to 201 Pemberwick Road on Saturday, December 6th from 12-6 PM.

Let’s eat, drink and be merry! 🍻✨

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

Decorate a Gingerbread House at 2CC!

Registration Required, $25/house preordered and $30 at the door
Limited Spaces Available

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

Reserve your gingerbread house here.

December 7
12:00pm
Email [email protected] for more information

Come celebrate the holidays with us at our annual Cookie Social!

All YMCA members and guests are invited to join in the holiday fun at the Y. Bake or bring your favorite cookies to share—though bringing a treat is not required to enjoy the festivities. Coffee will be served, and this year we’re thrilled to welcome the Greenwich Choral Society, who will join us to sing festive carols during the event.

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December 12 | 9:00am – 10:00am
YMCA Greenwich

Celebrate the holidays at Greenwich Historical Society’s Annual Holiday Festival! This years theme is A Night at the Museum! Dress in fun PJ’s and bring your entire family for fun holiday-themed crafts, decorate your own gingerbread people, and take photos with a special guest from the North Pole in the Historic Barn.

Take part in the holiday cheer with delicious, sweet treats and explore our beautiful, illuminated grounds. Warm up outside by the fire with some s’mores and hot cocoa or a winter beverage to round out an evening of holiday fun!

Please note that in the instance of inclement weather, the festival will be held on Sunday, December 14, 2025 from 4:00-7:00pm.

Get your tickets HERE. 

December 13, 4pm – 7pm
Greenwich Historical Society
Learn More

There is SNOWplace like the Cos Cob Library! Join us for our Winterfest Arts and Crafts Show. Spend a fun-filled afternoon sipping hot cocoa, listening to music, and doing some crafts. Don’t forget to stop by our community room and vote for your favorite Gingerbread house. There will be live performances featuring the Cos Cob School Chorus and Fairfield Brass Quintet as well as art and crafts for purchase and a Toys for Tots drop-off.

Winterfest Schedule

• 1pm – 3pm: Gingerbread House Contest Display and Voting
• 1pm – 2pm: Fairfield Brass Quintet
• 2pm – 2:30pm: Cos Cob School Chorus
• 3pm: Winner of the Gingerbread House Contest Announced

Saturday, December 13 from 1:00pm to 3:00pm
Cos Cob Library

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.

December 12th, 13th, 19th and 20th
4:00pm-8:00pm
More Details

Register HERE. 

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

December 14
4:30pm
Register at chabadgreenwich.org/

Join the Community Wide Pre-Chanukah celebration in Old Greenwich.

• Entertainment – Children & Adults
• The OG Menorah Rise – Building the OG Menorah
• Chanukah Land – Food Stations, Art & Crafts, and Chanukah Market

December 7
3:00pm – 5:00pm
The Sound Beach Fire Station 

Build and decorate your own ‘gingerbread’ house with graham crackers, frosting, and candy. The library will provide supplies, you supply the creativity. Dress for mess! Please only register the number of children in your family unit as each child will get their own house. This is not a drop-off program; each child must have an adult with them at all times. Space is limited and registration is required 

Wednesday, December 17 at 4:00pm for Preschoolers (Ages 3-5)
Wednesday, December 17 at 5:30pm School Age (Ages 5-12)

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

Pre-movie Activities

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

Complete Registration Information (PDF)

Saturday, December 20, 2025 | 5pm (Movie starts at 6pm) 
Bendheim Western Greenwich Civic Center
Buy Tickets Here 

Noon Year’s Eve is a fun, family-friendly celebration for kids to ring in the “new year” at a kid-friendly hour! The event includes a lively countdown to noon, complete with festive music. Kids can enjoy crafting fun party hats, and confetti cannons. The highlight of the event is the big balloon drop at noon, signaling the start of a brand new “year” filled with excitement and joy!

December 31, 2025 | 11:30am 
Greenwich Library

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

After more than three decades, the Holiday Train Show continues to delight as New York City’s favorite winter tradition and a can’t-miss adventure. The timeless magic of rail travel fills NYBG with seasonal cheer as model trains travel over famous bridges and through familiar city settings, bringing nearly 200 twinkling landmark replicas—including new surprises for 2025/2026—to life under the glass of the warm and welcoming Enid A. Haupt Conservatory. Get up close to see these miniature masterpieces, each one meticulously crafted from plant parts like palm fronds, pinecones, and cinnamon sticks. Outside on the Conservatory Lawn, a glowing mountain-scape brimming with even more trains and picture-perfect moments is yours to explore.

On select evenings, journey through the exhibition with friends and loved ones after dark to see the show in a charming new light during Holiday Train Nights. Whether young or old, the Holiday Train Show has sparked delight in generations of visitors—and it’s the city’s best way to celebrate the season with all your loved ones!

November 15 – January 11
2900 Southern Blvd, Bronx, NY 10458-5126
Get You Tickets Here! 

⭐ 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 202 here

November 21 – December 31
Kensico Dam Plaza, 1 Bronx River Pkwy, Valhalla, NY
Get You Tickets Here! 

New York’s family-favorite holiday tradition returns, as millions of lights and hundreds of illuminated animals spread across six lantern trails. Holiday Lights is a festive night out with friends and family as we celebrate wildlife and enjoy immersive light experiences, hands-on activities, holiday entertainment, and delicious food and drinks. Beloved favorites return, including the Holiday Train and Enchanted Sea – plus NEW surprises including thrilling snow tube slides, an epic illuminated ice-themed throne, virtual snowball throwing, and much more.

Reserve Tickets Now at BronxZoo.com

November 21, 2025 — January 4, 2025
Bronx Zoo, 2300 Southern Boulevard, Bronx, NY
https://bronxzoo.com/holiday-lights

November 21 – December 30
5pm – 8:00pm
*Open 5pm – 8:30pm on Saturdays*

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

The Holiday Wish Express is rolling back into Stamford beginning November 22! The beloved tradition will run on weekends and select dates through the end of December. It transforms 22,000 square feet at Stamford Town Center into New England’s most spectacular indoor holiday attraction and interactive experience. Purchase your tickets now and be sure to use code GREENWICHMOMS for 15% off!

November 22 – December 28 (on select dates)
Stamford Town Center
www.theholidaywish.com
Tickets from $35.00 (Adults) and $25.00 (Children).
For group arrangements and private events, reach out to [email protected]

Shark-Diving Santa Santa Claus will be diving with sand tiger sharks in the Aquarium’s Ocean Beyond the Sound exhibit most weekends in December! This experience is free with Aquarium admission. Click Here for Aquarium Tickets

“Rudolph the Red-Nosed Reindeer 4D Experience” The most famous reindeer of all is lighting up our 4D Theater 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 4!Tickets for a 4D movie are $7.95 per person ($6.95 for Aquarium members). Aquarium admission is optional. Click Here for 4D Tickets

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, it evaporates as it hits the floor, so no shoveling will be required. This experience is free with Aquarium admission. Click Here for Aquarium Tickets

Members Only Breakfast with Santa Members are invited to join us in their pajamas for our annual Breakfast with Santa on Saturday, December 6 from 8 – 10 a.m. During this festive morning, guests will enjoy a delicious breakfast buffet while taking photos with Santa Claus! Plus, enjoy holiday crafts, treats, and a showing of Rudolph the Red-Nosed Reindeer 4D in our theater. This 10-minute film uses the same stop-motion animation as the beloved television classic. You are welcome to wear your favorite pajamas or festive holiday attire! Click Here to Register

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 2025 together, but not at the stroke of midnight. Don’t miss family-friendly activities including magical performances, 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/

HAPPY HOLIDAYS FROM GREENWICH MOMS!