2022 WestportMoms Holiday Events Guide - Westport Moms

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 Westport Moms has organized all the best activities in Westport, Norwalk and the surrounding areas into one, easy to follow guide! We are excited to present the WESTPORTMOMS HOLIDAY GUIDE – Your one stop guide to the best winter activities in the area for you and the whole family!


Ice Skating at Longshore – Opening November 25th

Longshore offers ice skating lessons and activities all winter long at the WPAL Rink at 260 Compo Road South! Longshore Ice Rink hosts parties and private events, and has skate rentals available for all, so click here for more info!

Longshore WPAL Ice Rink
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Wreath & French Truffle Making Workshop at MOCA Westport

Michele Sinacore of Blossom + Stem Floral Design of Westport and Aarti Khosla of Le Rouge Handmade Chocolates will join forces with MoCA Westport to bring you a classic door wreath and french truffle making workshop.Participants will create a classic door-sized wreath form using a variety of fresh greens, ribbons and embellishments. Then move on to creating a decadent box of hand rolled French truffles to share with family and friends this holiday season.

You’ll leave with a gorgeous wreath and a box of 9 hand-rolled truffles. **Bring a pair of pruners for wreath making!

MOCA Westport –November 29th

WestportMoms Holiday Shopping Event

Please join us at the Westport Playhouse Barn anytime from 9am-2pm on Friday, December 2nd for our 6th Annual Holiday Shopping Event! We will have amazing vendors as always, and warm drinks and treats to keep those – inside and outside- feeling festive during the holiday season! Come shop for you- or someone you love! Happy Holidays!

Friday December 2
9:00am – 2:00pm 

Westport Wakeman Farm Tree Lighting

You’re invited to the Annual Wakeman Town Farm Holiday Tree Lighting Celebration on Friday, Dec. 2 from 4:30 p.m.-6:30 p.m.

It’s a festive, fun and free event, thanks to our sponsor Freudingman & Billings, for the whole family. Enjoy free sweet treats from The Porch & Sweet P Bakery, and hot chocolate from The Granola Bar. We’re featuring a variety of local school musicians playing some Christmas and Chanukkah favorites. Join us as First Selectwoman Jennifer Tooker lights up the Wakeman tree to kick off the season! 

Friday, Dec. 2 from 4:30 p.m.-6:30 p.m.
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Westport Holiday Stroll

In 2022, Dan Woog’s “06880”‘s first-ever Holiday Stroll featured packed sidewalks, folks wandering in and out of stores for gifts (and freebies), and tons of old-fashioned neighborly fun. This year, the Westport Downtown Association is co-sponsoring the event with “06880” and will be listing all promotions that businesses will be offering on https://westportdowntown.com/events/theholidaystroll!

Saturday, December 3
5:00pm – 7:00pm 

Westport Firefighter Santa Gift Run

Each year, the Westport Fire Department organizes the Santa Run, a fun way for families to get a visit from Santa, and a great fundraiser for the Westport Fire Department. Registration is now open for the 2022 Santa Run. If you would like to join our email list for the Santa Run, please send an email to [email protected]

Dates are below:
Thursday, December 8th
Friday, December 9th
Saturday, December 10th
Thursday, December 15th
Friday, December 16th
Saturday, December 17th

Thursday-Saturday, December 8th-10th
Thursday-Saturday, December 15th-17th
Email for more info: [email protected]

Holidays at the Maritime Aquarium

Shark-Diving Santa   

Santa Claus will join The Maritime Aquarium’s dive team in December to help demonstrate that sharks aren’t the blood-thirsty killers of myth. Several times each week through the holiday season (workload permitting), Santa will strap on his custom scuba outfit and enter the Aquarium’s 110,000-gallon “Ocean Beyond the Sound” exhibit, which is home to 7- and 8-foot sand tiger and lemon sharks. He’ll swim up to the exhibit window and pose with children, so bring your camera for a unique holiday photo. Santa is expected to participate in dives throughout the month of December. Please check the Aquarium’s website – 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 17 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 www.maritimeaquarium.org (Tickets for this experience are required for all guests, including those under 3 years old.)

“The Polar Express 4D Experience”  – Opens November 25 for multisensory film experiences each hour.

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. 

Fri., Nov. 25 (the day after Thanksgiving) and will play daily through Jan. 2.
Maritime Aquarium, 10 N Water St, Norwalk, CT 06854

Selfies with Santa at the SoNo Collection

What’s that sound? Santa’s in town! Capturing magical moments with St. Nick is easier than ever—all you need is your phone or camera! Join us Black Friday through Christmas Eve to snap photos with the big guy himself in Santa’s Candy Shop!

Share with loved ones, post on social media, and create memories.

Santa’s Candy Shop is a unique first-to-market selfie experience presented by The SoNo Collection and its parent company Brookfield Properties.

November 25 – December 24
Fridays- 5PM–9PM &
Saturday & Sunday-11AM–5PM
Bloomingdales Court, Level 1, SoNo Collection


Greenwich Reindeer Festival

Santa and his three LIVE reindeer return to Greenwich for the 14th Annual Greenwich Reindeer Festival & Santa’s Workshop presented by Jenny Allen / Compass Real Estate, “the North Pole on North Street,” Sam Bridge Nursery & Greenhouses, 437 North Street, Greenwich, Connecticut, from November 25 to December 24, 2022. The cherished town tradition continues for the fourteenth consecutive year at this expansive nursery where visitors can have their photo taken with Santa, meet the reindeer and also enjoy Santa’s Workshop, which provides more space for families, “Letter Writing to Santa Station” sponsored by Greenwich Pediatric Dental Group and a “Reindeer Coloring Station” sponsored by Jenny Allen/Compass 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. A Kids In Crisis Giving Tree will also be available for people to support their important mission.

November 25 – December 24
Sam Bridge Nursery & Greenhouses, 437 North Street

Greenwich Botanical Center Holiday Tidings, Trimmings and Toasts

Join us for some holiday cheer and get creative putting together some festive decorations for your home. A variety of greens will be available for wreaths, swags, mantles, urns and centerpieces as well as holiday plants to brighten up your home. Greenhouse volunteers will be on hand to help you. If you are short on time, just join us for a cup of coffee or signature cocktail and pick up some premade trimmings. You won’t want to miss the Festive Fun!

$90 GBC Member | $125 Non Member

To register, visit www.greenwichbotanicalcenter.org/events

November 30, 10:00am or 5:00pm
Greenwich Botanical Center

Greenwich Historical Society Winter Festival

WINTER MARKET: Our annual Winter Market will be held at Christ Church. Find something for everyone on your list at our thoughtfully curated holiday market with vendors offering the finest in Holiday Gifts, Jewelry, Clothing, Specialty Foods, Flowers and items made to be enjoyed with family & friends.

FESTIVAL OF TABLETOP TREES: Place a bid in our fourth 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.

HOLIDAY FAMILY FESTIVAL: Celebrate the Holidays at the Greenwich Historical Society’s Holiday Festival. Bring your entire family for photos with Santa, holiday crafts and gingerbread decorating.

December 1 – December 3
Christ Church and Greenwich Historical Society

First Light Old Greenwich

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.

December 3
Sound Beach Avenue, Old Greenwich
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Greenwich Botanical Center Holiday Centerpiece Workshop

Sarah Wang of Sweet Blooming Floral will lead the class in creating a holiday centerpiece to grace your holiday table. She is the founder of sweetblooming.com and lead floral designer based in Greenwich, CT and studied at New York Flower School, one of the most celebrated floral design schools in the world.

Flowers & vessel included. $140 GBC Member | $160 Non Member

To register, visit www.greenwichbotanicalcenter.org/events

December 22, 10:30am
Greenwich Botanical Center

Holiday Wish: Follow the Magic

Taking place this Holiday Season at Stamford Town Center, Downtown Stamford, CT, Holiday Wish is an immersive walk-through event that delivers a sensory entertainment experience.

A new Holiday Tradition designed to put families into the Spirit of the Season, Holiday Wish incorporates visual storytelling at its best.  Along the journey though Holiday Wish, guests follow the magic through each feature. From the Elves’ Quarters, where they care for the reindeer, to an epic Twinkling Forest and Frozen in Time winter world.  Children will love the Holiday Wish filled interactive wonderland, featuring a digital snow snowball fight with a virtual snowman, and much more.   Children will love the friendly challenge of being enlisted by the elves at Santa’s Workshop who need inspiration to overcome their creative blocks. Only one thing sparks their inspiration: children believing in the magic of the season.

The experience culminates in the grand finale at the North Pole where – if all goes as hoped! – the elves will be busy making toys in their workshop. Here, guests revel to their heart’s content in giant walk-in presents, a visit to Santa’s throne, and an animatronic snow bear band. Guests experience the magic of The North Pole, completing an inspired exploration that ensures holiday wishes come true. And restores the wonder of the season.

Also located within Holiday Wish is the Christmas in America Retail Shop, a shopping area featuring treasured mementos, snacks, candy and more.

November 11 – December 24
Stamford Town Center, Downtown Stamford, CT

Stamford’s All New Holiday Stroll

Welcome to the All New Holiday Stroll. Walk through wonder. Explore monumental interactive displays, captivating illumination and a winter wonderland for a holiday experience made to inspire. The stroll includes a Winter Beer Garden, Christmas Village, Rides and Games. 

November 18 – December 24
Mill River Park, Stamford, CT

Winter Wonderland Drive Through

Westchester’s Winter Wonderland Drive-Thru Holiday Light Extravaganza, presented by Westchester Medical Center Health Network, will return to Kensico Dam Plaza bigger and better than ever with thousands of more lights and magical holiday animations. Guests will be dazzled and delighted along the 1.2 miles of holiday lights by several new additions for 2022 including: a new North Pole and live Santa display; breathtaking Kaleidoscope Alley; expanded Peace on Earth LED display with animated trumpets and angels; and more electrifying lights surrounding the largest holiday Christmas tree in Westchester! And that is not all, for the grand finale, guests will be able to make their New Year’s wish upon a new thirty-foot glistening star that will be featured at the end of the interactive show, all right from the warmth and safety of your own car!

November 25 – January 1
Kensico Dam Plaza, 1 Bronx River Pkwy, Valhalla, NY

Lumagica Light Show at Harvest Mood & Orchard

LUMAGICA USA returns to Harvest Moon with an all new light show. After a fruitful harvest season, the orchard is transformed into an Enchanted Forest. Filled with over 750,000 lights, whimsical creatures and lots of surprises. Be ready to step into a world of wonder. The natural landscape of the Orchard is a canvas for design and creative storytelling.

The over ½ mile trail will take you on a journey through the 6 spaces, Sparkling Light, Into the Wonderland, Magical Trees, A Great Celebration, Treats and Sweets, and Beyond the Forest. Guests can expect a 20 ft reindeer, a soaring parrot, lots of new photo ops, light tunnels and a Light to music show. 

So, grab a warm drink and a light up wand on your way in and get into the festive spirit this holiday season. Enchanted Forest, the holiday event you won’t want to miss.  

November 18 – December 31, Opening Hours 4pm – 9pm
Harvest Moon, 130 Hardscrabble Road, North Salem, NY 10560

Rob Mathes Holiday Concert

The annual Rob Mathes Holiday Concert is back live and in-person this year at The Performing Arts Center at Purchase College. Two shows will be presented on Friday, December 16, and Saturday, December 17, at 8:00 p.m. Tickets are available through artscenter.org or first and second row seats can be purchased through the concert’s nonprofit beneficiary Food Rescue US – Fairfield County. Rob Mathes is an Emmy award-winning, Grammy, Tony and Drama Desk Award nominated musician and Greenwich, Connecticut, resident. He is usually the man behind the music, producing albums, arranging and orchestrating, and is a sought-after music director. His annual holiday concert, a holiday tradition in the New York City/Connecticut area for 29 years, is his time to take center stage to the delight of his many fans.
The Rob Mathes Holiday Concert puts a new, intensely musical spin on a holiday concert. Featuring some of NY’s finest musicians, it is an eclectic evening of high-energy pop, jazz, and rhythm and blues, with original holiday songs and many newly arranged classics. They all have a unique Rob Mathes touch on them. Rob’s Dad is a Dylan fan, his Uncle a big band trombonist and his Mother and Aunt play Mozart and Chopin all day. Rob brings together influences from Duke Ellington to Joni Mitchell, from Jeff Beck to Vaughan Williams, and the evening is always quite a musical journey. Joining Rob on stage is his all-star band with a six-piece horn section featuring Jeff Kievit on Trumpet, Will Lee from the Late Show with David Letterman and The Fab Faux on bass, Billy Masters on guitar, Gunnar Olsen on percussion, Rick Knutsen on keyboards, and James “D Train” Williams and Vaneese Thomas, two local legends who sing RnB and Gospel and who have stolen the show for the better part of two decades. Also performing with Rob is a 40 voice choir.


December 16 & 17
8:00pm, The Performing Arts Center at Purchase College
Purchase Tickets

Rudolph the Red Nosed Reindeer: The Musical at the Palace

Come see all of your favorite characters from the special including Santa and Mrs. Claus, Hermey the Elf, Bumble the Abominable Snow Monster, Clarice, Yukon Cornelius, and, of course, Rudolph, as they come to life in RUDOLPH THE RED-NOSED REINDEER: THE MUSICAL. It’s an adventure that teaches us that what makes you different can be what makes you special. Don’t miss this wonderful holiday tradition that speaks to the misfit in all of us.

November 26 at 2:00pm and 6:00pm
Palace Theatre, 61 Atlantic St, Stamford
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Photos with Santa at the Westchester Mall

The ultimate holiday tradition awaits! Santa is located on Retail Level 1 near Nordstrom. Secure your spot today and make your reservation here.

November 12 – December 24
The Westchester, 125 Westchester Ave, White Plains, NY
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Sleighbells on the Avenues

“Sleighbells on the Avenues” brings Holiday Excitement to Larchmont Village!
Larchmont invites you to join in as the village is filled with the sound of sleigh bells as horse drawn carriage rides, visits with Santa, and tree lightings illuminate the downtown.  A series of free events organized by the Larchmont Chamber of Commerce and supported by local merchants will take place throughout the holiday season and are outlined below and at larchmontchamber10538.org/holidayevents
Saturday November 26
–  “Find Frosty” Scavenger Hunt for Kids. Pick up your Frosty passport at Village Mercantile and scout out Frosty charms in stores throughout town while taking advantage of small business Saturday promotions.   Prizes for the winners!
Saturday December 3
–  Horse Drawn Carriage Rides 12-3 pm.  Climb on board one of 3 sleighs for a complimentary sleigh ride at either of 2 stops: the corner of Larchmont Avenue/Addison Street, or Chatsworth/Vanderburgh Avenues.  Carolers will serenade while you wait!
–  Santa & Mrs. Claus will greet from a Snow Globe in Addison Park next to CVS from 12-2 pm
–  Elsa & Olaf – 12-2 pm. Elsa will sing and visit with fans in the pocket park on Palmer Avenue between Stephanie’s Kloset and Chase Bank.  Olaf will greet near Anderson’s Book Store on Chatsworth Avenue.
–  Tree Lighting – 6 trees donated by Larchmont Nurseries will be decorated by local charities with a lighting in Constitution Park at Dusk.

November 26 & December 3
Larchmont, NY
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NYBG Holiday Train Show

NYBG’s Holiday Train Show—a favorite holiday tradition—has been making memories for over 30 years! See model trains zip through an enchanting display of more than 190 replicas of New York landmarks, each delightfully re-created from natural materials such as birch bark, lotus pods, and cinnamon sticks.

Plus, take in NYC’s largest outdoor holiday light experience at NYBG GLOW, returning for its third year with even more illuminated displays. Thousands of dazzling, energy-efficient lights and whimsical, picture-perfect installations reflect the surrounding gardens and collections, creating a spectacle not to be missed. These special evenings feature music, experiences, food, and more—making for the ultimate night out this season.

November 19 – January 16, 10am – 6pm
New York Botanical Garden, 2900 Southern Boulevard, Bronx, NY

Bronx Zoo Holiday Lights

Join us for a family holiday festival at the Bronx Zoo. During the evenings, the park comes to life with holiday cheer as immersive light displays, custom-designed animal lanterns and animated light shows sparkle across the zoo. The celebration includes festive entertainment, seasonal treats, the Holiday Train, and classic holiday music. The walk-through experience is a beloved tradition, enchanting and fun for all ages.

November 18 – January 8, 2023
Bronx Zoo, 2300 Southern Boulevard, Bronx, NY

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