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 2023 GREENWICH MOMS HOLIDAY GUIDE – Your one stop guide to the best winter activities in the area for you and the whole family. Thank you to our sponsor, Eugene’s Music & Learning Studio for making this guide possible! From private lessons in-home, in-studio, and online, to Early Childhood and group classes in their fully equipped studios, Eugene’s Music & Learning Studio will find a way to bring the love of music and learning into your life.

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

The Woman’s Club of Greenwich “Holiday Boutique”
November 17 @ 10:00 am – 5:00 pm
November 18 @ 10:00 am – 4:00 pm

The Junior League of Greenwich – The Enchanted Forest 
November 17 @ 7:00 pm – 10:00 pm – Opening Cocktail Party
November 18 @ 10:00 am – 4:00 pm – The Enchanted Forest Family Days
November 19 @ 10:00 am – 3:00 pm – The Enchanted Forest Family Days

Holiday Sip & Shop at Abilis Gardens & Gifts
November 29 @ 5:00 pm – 8:00 pm

The Holiday Gift Bar at Dudley Stephens with 1212 Pajamas
Saturday, 12/2 from 10am-5pm 6 West Putnam Ave, Suite 201
Come shop Dudley Stephens and 1212 Pajamas.
Bring your little ones for complimentary pictures with Santa, and special holiday arts + crafts activities!

Greenwich Academy Holiday Boutique
December 3 @ 10:00 am – 5:00 pm

Greenwich Historical Society – Holiday Boutique
December 6 @ 5:30 pm – 8:00 pm
December 7 @ 9:30 am – 4:30 pm

HOLIDAY ACTIVITIES IN GREENWICH

Friday, Nov. 17:  Cocktail Party 7:00 – 10:00 pm – Join us for a fun, very social ‘Sip, Stroll, and Shop’ in the stunning Grand Hall of the Bruce Museum, catered by Aux Delices. Walk through and bid on the trees from the Enchanted Forest, one more stunning than the next. Enjoy the galleries of the Bruce Museum for the first hour of the reception, including a brand-new exhibit. Get your holiday shopping done early in our Holiday Boutique for gifts you won’t find anywhere else.

Saturday and Sunday, Nov. 18-19: Family Days – Bring your children for a special Holiday experience on our Family Days, which include: 

• The Enchanted Forest – Visitors can view our exclusive, individually designed trees decorated by local businesses, designers, and individual contributors. The online auction to bid on these trees will be open all weekend.
• Holiday Boutique Shopping – Start your holiday shopping early with J. Wilder Imports, Caye Joaillier, B’s Hive, Patent of Heart, Brushstrokes_by_tam, Glouja, Ann Foster Designs, Camile & Co and more to come. Shopping will be open all weekend!
• The Giving Shop – The Children’s Giving Shop at The Enchanted Forest is a child-centered area where children 5 and older can shop independently for holiday gifts. Staffed and stocked by JLG members, each child will be escorted through the shop without parents to find the perfect gift on their shopping list for friends and family. Volunteers and JLG elves will assist children with their shopping and wrap all of the presents, so the gifts remain a surprise for the recipients.  It is sure to be a memorable, unique, and fun experience for the little ones.
• Breakfast with Santa – Enjoy an exclusive breakfast with your little ones and Santa starting at 9 am Saturday & Sunday.
• Gingerbread House Decorating – Decorate your very own gingerbread house to take home! An assembled house is provided, along with all of the candy and icing you could wish to create your own masterpiece. Take-home kits are also available and can be purchased at the event or online with the rest of your tickets to be picked up at the event.

November 17 – November 19
Friday, Nov. 17: Cocktail Party 7:00 – 10:00 pm
Saturday and Sunday, Nov. 18-19: Family Days (Saturday, 10 am – 4 pm, Sunday, 10 am – 3 pm)
Get Your Tickets

Eugene’s Music & Learning Harp Class

We are looking forward to this Holiday Season and want to celebrate all the wonderful voices we have at the Studio!

Do you know which ancient Irish instrument has magical powers? The Harp! The holiday season is right around the corner – join us for a FREE group harp class with Erica on Sunday, November 19th
Children: 2:00 PM
Adults: 5:30 PM

Please RSVP to reserve your spot at [email protected] or 914-259-8389!

December 15
5:00pm – 6:00pm
Eugene’s Studio, 603 N Main St, Port Chester, NY 10573
[email protected]

Eugene’s Music & Learning Studio Caroling Party

We are looking forward to this Holiday Season and want to celebrate all the wonderful voices we have at the Studio!

Friday, December 15th from 5-6 PM we will be hosting a caroling party. All are invited to sing along to holiday favorites!

Please RSVP by December 8th to reserve your spot at [email protected] or 914-259-8389!

December 15
5:00pm – 6:00pm
Eugene’s Studio, 603 N Main St, Port Chester, NY 10573
[email protected]

Santa Claus and his three LIVE reindeer are coming to town, as they return to Greenwich for the much anticipated 15th Annual Greenwich Reindeer Festival &
Santa’s Workshop presented by Jenny Allen/Compass Real Estate, to the “North Pole on North Street,” Sam Bridge Nursery & Greenhouses, 437 North Street, Greenwich, Connecticut, from November 24 to December 23, 2023.

The cherished town tradition continues for the fifteenth consecutive year at the expansive nursery where visitors 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/Compass, Letter Writing to Santa Station for children sponsored by Greenwich Pediatric Group, Raffle to win two different Mercedes-Benz Kids Electric Cars and a “Name the Reindeer Contest,” while families wait in line for their photo with Santa to create special holiday memories. New this year is the Naturepedic Organic Dog Bed Raffle. Everyone who brings their Dog for a Photo with Santa can enter to win this awesome bed for their dog! Santa will draw the lucky person’s name Saturday, December 23. A portion of all photos with Santa will 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 fifteenth year.

November 24 – December 23, 2023
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

Friday, December 1 is our Annual Tree Lighting at Town Hall, beginning at 4 p.m. Santa Claus and friends will be visiting; entertainment will be provided by Allegra Dance and Greenwich A cappella.

Dec. 1 is also the beginning of our Holiday Photo Contest which runs through Dec. 15. Submit a photo showing your favorite part of the holidays in Greenwich and you’ll be entered for a chance to win a holiday prize package.

December 1
Begins at 4pm
Greenwich Town Hall

Kids will start class by making their clay-dough material from scratch; learning to mix the recipe of safe and sensory engaging ingredients together. We will then roll and sculpt our clay-dough material into fun-filled (*non-edible) cookie creations. We will use different natural elements to make a variety of decorative textures; press with bark, roll with pinecones, and even explore the marks and patterns of fingerprints! Kids will have the option to finish off their *decorative cookies* with tiny, naturally found treasure embellishments of their choosing. Children will have so much fun in this very hands-on class;  building their cookie creations, using their imagination and their fine motor skills. Class time includes a themed story-time and a fresh-air field trip walk around our beautiful park grounds. Come dressed for the weather and loads of creative play! All materials will be provided and kids will take home their collection of “creative cookies” at the end of class to enjoy at home! This is a drop-off class for ages 3-7.

$65/ GBC Member | $75/Non Member

Saturday, December 2 | 10AM-12PM
Greenwich Botanical Center
More Information

Decorate a Gingerbread House at 2CC!

Registration Required  – $35/each
Limited Spaces Available

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

December 2
9:30am – 11:00am
Email [email protected] for more information

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 2023 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 2nd @ 5:00 PM in Old Greenwich! ❄️

December 2
5:00pm-8:00pm
Sound Beach Avenue, Old Greenwich
More Details

Join the celebration that draws together Friends of the Byram Shubert Library and the entire Byram community including school choirs!  & Crafts. 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. 

Sponsored by the Friends of the Byram Shubert Library

December 2
4:00pm-6:00pm
Byram Shubert Lbrary
More Details

Join Arch in Bloom from 12-6pm for music, refreshments & kid friendly activities while you shop for handmade Elves & Co. wreaths, fresh-cut trees, ornaments & seasonal gifts! 

December 2
12:00pm-6:00pm
201 Pemberwick Road, Greenwich
Arch in Bloom

Grab a friend or come make a new one and learn how to make a beautiful holiday wreath using natural and enhanced decorations such as seed pods, pinecones, luxe ribbon, dried berries, and more. We will have refreshments on hand to accompany the learning and merriment!

To register, visit www.greenwichbotanicalcenter.org/events

Monday, December 4 | 6PM
Greenwich Botanical Center
More Information

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 9th.

Festival of Tabletop Trees December 6 – 8th (9:00am – 5:00pm)
Festival of Tabletop Trees December 9th (11:00am – 7:00pm)
Holiday Festival December 9th (4pm – 9pm)
Greenwich Historical Society
https://greenwichhistory.org/ghs-events/

Celebrate Chanukah with Chabad of Greenwich! Join us for a night of festivities, complete with a Grand Menorah Lighting and a Chanukah Concert. In addition, on December 8, join for a Shabbat Dinner with Nissim! Fun for all ages!

December 9
6:15 Lighting, 7:30pm Concert
Shabbat Dinner with Nissim, Friday, December 8 6:30pm
Register at chabadgreenwich.org/

Bring the entire family for photos with Santa and a visit to the festive Historic Barn, complete with gingerbread decorating and crafts in Santa’s workshop. Take part in the holiday cheer and enjoy a winter beverage while listening to performances by the Connecticut Yuletide Carolers. Explore the beautifully illuminated grounds and delight in the artistic prowess of professional Ice Sculptor Bill Bywater as he creates a wintry marvel from giant blocks of ice. Enjoy tasty treats from Fryborg Food Truck and warm up outside by the fire with some s’mores and hot cocoa to round out an evening of family holiday fun!

December 9th, 4pm – 9pm
Greenwich Historical Society
https://greenwichhistory.org/ghs-events/

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. Donations for the Holiday Gift Drive for Teens at Yale Children’s Hospital will be joyfully accepted by Mrs. Claus. 

December 9
8:00am at Coffee for Good
Email [email protected] for more information

Tickets go on sale November 15 for Holiday Happenings & Movie Night which will be held Saturday, December 9 at Bendheim Western Greenwich Civic Center.

We will have holiday music and pajama party, inflatable snow globe and photo opportunities, stuff your own holiday bear and more! Tickets are $10 each.

Saturday, December 9
Bendheim Western Greenwich Civic Center
Buy Tickets at https://www.greenwichct.gov/webtrac

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

Celebrate the holidays with Cups N’ Cones by getting Ice Cream with Santa!

December 10
3:00pm – 5:00pm
Cups N’ Cones

Let GEMS help you celebrate the holidays this December! A decorated ambulance and GEMS staff will visit your house to deliver YOUR Gift(s) to your child.

December 15, December 16 and December 23 

Drop off a gift to Greenwich EMS AT LEAST 5 days prior to our visit and our staff will deliver a special experience and surprise to your child!

Sign Ups Open 11/19! Limited Availability for 4-8pm. 

$25/child

December 15, 16, 23
4:00pm-8:00pm
Sign Ups Open Sunday 11/19
More Details

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

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 from Nov 17th – Jan 7th, select dates only.

Reserve Tickets Now at BronxZoo.com

November 17 – January 7, 2023
Bronx Zoo, 2300 Southern Boulevard, Bronx, NY
https://bronxzoo.com/holiday-lights

Visit our Farm this holiday season for a magical, one-of-a-kind, walk-through light experience!

Prepare to be dazzled! We are so excited to announce this season’s Festival of Lights 2023, when our orchard is magically transformed into an illuminated forest full of marvelous structures and festive decorations!  Over half a million brilliant lights set the farm aglow in the form of whimsical creatures, light-changing orbs, thematic installations and interactive light displays.

Guests will step into a nighttime world of fantasy on the half mile trail, taking them on a wonderous journey into our orchard where they will walk through illuminated tunnels, enjoy featured lights to music shows, and have fun posing at our all new photo ops!

So grab a warm drink and a light up wand as you make your way in and be prepared to be immersed in a festive, holiday spirit. Harvest Moon’s Festival of Lights, the seasonal event sure to delight guests of all ages! You won’t want to miss it!

 NOTICE: The path includes hills and some areas with uneven surfaces. All-terrain strollers recommended. 

November 17 – December 31, Opening Hours 4pm – 9pm
Harvest Moon, 130 Hardscrabble Road, North Salem, NY 10560
More Info

New York City’s Most Beloved Holiday Tradition Is Back!

The Holiday Train Show returns bigger than ever with more trains and an all-new, outdoor train display. Start on the lawn to capture your perfect holiday photos at our outdoor mountainscapes and then watch trains zip past nearly 200 iconic New York landmarks under the warmth of the Conservatory. After dark, join us for NYBG GLOW and discover the beauty of our landscape and historic buildings, illuminated across the grounds. And don’t miss the return of our fan-favorite Bar Car Nights, 21-and-over evenings featuring the Holiday Train Show and curated cocktails. These special evenings feature music, experiences, food, and more—making for the ultimate night out this season.​

November 17 – January 15, 2024, 10am – 6pm
New York Botanical Garden, 2900 Southern Boulevard, Bronx, NY
More Info

This festive season, Stamford becomes the gateway to the North Pole’s wonders! You and your family are invited aboard the Holiday Wish Express, an immersive holiday odyssey that promises delights for all ages. With an exhilarating virtual train ride, meticulously crafted themed rooms, and beloved characters, all centered around the captivating tale of Teddy’s Christmas Adventure.

Embark on a Journey with Teddy and Friends! The journey starts aboard the Holiday Wish Express Train, led by the charismatic Train Conductor. As the train chugs along, find yourself transported to the mesmerizing Glacier Island, where playful Polar Bears and Penguins await. Traverse the luminescent Starlit Forest, home to frolicsome Deers, Rabbits, and the melodious Raccoon family.

The journey continues as you visit the Reindeer Stables before taking a stroll down North Pole’s Main Street. Under the watchful eye of the jubilant Mayor of the North Pole, you’ll then be guided through the luminous Portal of Light, leading you to Santa’s Workshop. Presided over by Mrs. Claus and bustling elves, this magical space allows little ones to craft wishes in the North Pole Mailroom.

But the enchantment doesn’t end there. Dive into the snow for an interactive snowball fight and step into Teddy’s House of Sweets. A treasure trove of candies, toys, and the chance to adopt a Teddy to cherish forever.

November 18 – 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]

November 24 – December 24, 4:30pm – 7:30pm
Mill River Park, Stamford, CT
www.theholidaystroll.com

November 24 – December 31
Kensico Dam Plaza, 1 Bronx River Pkwy, Valhalla, NY
Get You Tickets Here! 

December 3 at 2:00pm and 6:00pm
Palace Theatre, 61 Atlantic St, Stamford
More Details

This year, the Westport Downtown Association is co-sponsoring the third annual Holiday Stroll with Dan Woog. This year’s event will feature participating retailers and restaurants offering deals and promotions, activities for children (face painting, balloon artists, and a photo booth), and a performance by the Staples Orphenians. The stroll will begin with carolers at Sconset Square and conclude on Upper Main Street.

Saturday, December 2
5:00pm – 7:00pm 
More Info

December 2
Larchmont, NY
More Details

Shark-Diving Santa   

Santa Claus will join The Maritime Aquarium’s dive team most Saturdays in December to help demonstrate that sharks aren’t the blood-thirsty killers of myth. Santa will strap on his custom scuba outfit to enter the Aquarium’s 110,000-gallon “Ocean Beyond the Sound” exhibit, which is home to sand tiger and sandbar sharks. He’ll swim up to the exhibit window and pose with children, so bring your camera for a unique holiday photo. Please check the Aquarium’s website – https://www.maritimeaquarium.org/ – to confirm the dates when Santa can pull himself away from the North Pole and exchange his snow boots for swim fins

Breakfast with Santa Exclusive to Members

Members are invited to join us on Saturday, December 16 in their pajamas for a breakfast with Santa Claus! Bring your camera … Santa will be available for pictures. Please check the Aquarium/s website for details https://www.maritimeaquarium.org/member-events (Tickets for this experience are required for all guests, including those under 3 years old.)

“The Polar Express 4D Experience”  – Playing through December 31

A holiday tradition in The Maritime Aquarium at Norwalk goes to a new dimension – literally – as an exciting new version of the beloved film “The Polar Express” steams off the screen in the new 4D Theater. The animated film, featuring Tom Hanks as the voice of the conductor, will play every hour in the 4D Theater through Jan. 2, 2023.

“The Polar Express 4D Experience” is a 13-minute version of the 2004 film directed by Robert Zemeckis, based on the beloved Caldecott Medal-winning children’s book by Chris Van Allsburg. When a doubting young boy takes an extraordinary train ride to the North Pole, he embarks on a journey of self-discovery that shows him that the wonder of life never fades for those who believe. 

More Events to Come!

Will play daily through December 31
Maritime Aquarium, 10 N Water St, Norwalk, CT 06854
https://www.maritimeaquarium.org/

Every December, arranger, composer, producer, director and musician extraordinaire Rob Mathes rings in the holiday season with a spectacular celebration that features Mathes, his all-star band and a choir of “Saints & Friends.” This year’s concerts are celebrating 30 years of holiday concerts and are in loving memory of Rabbi Mark Golub – a dedicated and loyal friend and fan who never missed a Rob Mathes Holiday Concert.

These high-energy concerts includes rock, jazz and blues, with original tunes and new spins on holiday classics. With three concerts this year — Friday and Saturday nights at 8PM, and a maitinee on Sunday at 3PM — this year’s 30th anniversary will be extra special and you won’t want to miss it!

Rob has worked with most of the big name artists in the music industry — arranging, producing, directing, writing, recording and performing — with the likes of Bono, Bennett, Sting and Springsteen, and many more. But despite his busy schedule, Rob comes home for the holidays and shares his holiday tradition with us all. Please join us December 15, 16 or 17.

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 15 & 16, 8PM
Sunday, December 17, 3PM
The Performing Arts Center at Purchase College
VIP tickets (first 2 rows) and support Food Rescue US – Fairfield County available at: foodrescue.us/site/food-rescue-us-fairfield-county
Purchase Tickets

HAPPY HOLIDAYS FROM GREENWICH MOMS!