2023 Holiday Event 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 WestportMoms has organized all the best activities in Westport and the surrounding areas into one, easy to follow guide!

We are excited to present the 2023 WESTPORT MOMS HOLIDAY GUIDE – Your one stop guide to the best winter activities in the area for you and the whole family. Happy Holidays to all!

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 info@westportmoms.com and if appropriate we will add it! 


Sip ‘n Shop Event @ Trumpet

Join us THIS Thursday for a fun Sip ‘n Shop event at Southport’s Trumpet Boutique from 6PM-9PM. There will be food, drinks and a special gift with purchase, and 20% off all night, as well as all day 11/30 and 12/1! See you there!

Thursday, November 30th
Drinks, Food & Special Gift with Purchase PLUS 20% off!

Westport Holiday Stroll

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

Winter Market @ Westport Museum

This family-friendly winter market will bring the holiday spirit to downtown Westport. View our gingerbread village of local buildings, explore our local vendor booths, enjoy the warming fire and hot chocolate, and much more. While you shop, visit Santa and get a photograph! Santa is double checking his list and will have a candy cane or sticker for each visitor. While you’re here have a one-of-a-kind hand cut silhouette crafted right before your eyes. Reservations for silhouette appointments may be made in the form below. 

This is a free event offered on the grounds of the museum. Like our programs? We’d appreciate your support! Suggested donation of $5, continues our unique programming. 

Saturday, December 2

Westport Tree Lighting

Light ’em up! Westport’s annual tree lighting is set for Monday, December 4th at 5PM at Town Hall.

The Staples High School Orphenians will perform. Then the tree on the lawn in front will be lit. It’s a quick, fun ceremony. And everyone is welcome.

Monday, December 4th
5PM @ Town Hall

Gingerbread House Decorating @ Westport Museum

Grab your favorite person and decorate your very own gingerbread cookie for the holiday season! Each pair receives their choice of two gingerbread cookies, assorted candy, and icing to decorate as well as staff to give recommendations. These cookies will be a delicious seasonal souvenir. A great activity for parents and children, couples, and friends to be together during the most festive time of the year. 

Reservations may be made at 11AM, 1PM or 230PM; each workshop lasts for approximately 60 minutes. Workshops are limited to 6 pairs during each time slot, save your spot in the form below before we sell out! Tickets  are $15 for non-members, and $10 for members and include all materials. 

Saturday, December 9

LivFree on Ice @ PAL Rink at Longshore

LivFree celebrates the holidays with ice skating, an appearance from Santa, holiday carols, and a campfire!
DATE: December 9, 2023
TIME: 1:00 pm
LOCATION: Westport PAL Rink # Longshore
COST: $15 – Adults | $12 – Youth (12 & Under) | $5 Rentals

Gingerbread Family Event @ Weston Field Club

The Weston Women’s League is thrilled to host our annual Gingerbread event.
Please join us for the Family Gingerbread Event taking place on December 9, 2023. We are offering two separate time slots at 2 pm & 4 pm.

Kids will delight in decorating their own gingerbread houses, meeting with Santa Claus, and enjoying festive music of the holiday season.
To purchase tickets, click here or each out to us at [email protected].

Menorah Lightings (in and around Westport)

Watch the menorahs light up from town to town in Wilton, Weston and Westport.
December 10th @ 5PM – Come Light Weston’s Community Menorah! Live music, wrapped snacks, gelt and dreidels for everyone. Location: Weston Shopping Center
December 11th @5PM – Wilton Community Menorah Lighting! Join friends from Wilton for Live music, wrapped snacks, gelt and dreidels for everyone! Location: Wilton Town Green
December 11th @5PM – Come Light Westport’s Community Menorah!  Join us for live music, wrapped snacks, Chanukah gelt, dreidels and more. Feel free to watch from your car! Location: Anthropologie in Downtown Westport and Trader Joes Shopping Center, by the bank

Chanukah Wonderland at The Sono Collection

Sunday, December 10, 12:30- 2:30 PM
Chanukah crafts and activities
Menorah lighting 3:30 PM

RSVP Strongly recommended – SoNo Collection 100 N. Water St., Norwalk

Westport Playhouse Holiday Shows

The Lightning Thief – FAMILY FESTIVITIES – Grades 3rd-6th – Saturday, December 2nd

About: When teenager Percy Jackson discovers he’s a demigod, he and his friends embark on an epic journey to find Zeus’ missing lightning bolt and prevent a war among the gods. This dynamic musical adaptation of Rick Riordan’s bestselling bookThe Lightning Thief, features an exciting rock score.

A Sherlock Carol – December 19th-23rd
About: TWO BELOVED CLASSIC TALES. ONE THRILLING NEW MYSTERY. A SHERLOCK CAROL is a heartwarming holiday production for all ages—and a theatrical experience you’ll never forget!
For more info and tickets, click HERE!

Westport PAL Ice Skating Rink

WPAL Rink @ Longshore will be opening Friday November 24th. For party / private ice reservations you can check the schedule here on the website for available dates and information. For group skating lessons please call Westport Parks & Recreation at (203) 341-5090

11AM-9PM Open Skate – Check Calendar for detailed schedule
Weekends – $15/Adult and $12/Child

Weekdays – $12/Adult and $10/Child
$5 Rental for Skates
More Info


Holidays at the Maritime Aquarium

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

Holiday Happenings at Stew Leonard’s Norwalk

Stew Leonard’s in Norwalk is kicking off the 2023 holiday season with many family-friendly activities, including holiday-themed classes and even a special Breakfast with Santa!

Christmas Lighting Celebration – Thursday, November 30, 2023, at 5PM
Stew Leonard’s Norwalk store is kicking off the 2023 holiday season with its annual Farm Lighting celebration. The festivities begin at 5 p.m. with musical entertainment from the local school choir and an appearance by the Long Hill Fire Department fire truck.  Santa & Mrs. Claus will spend the evening mingling with families and handing out candy canes. Complimentary hot cocoa and cookies will be served. No registration is necessary for this free event.

Meet Santa Claus at Stew’s!
November 24 – December 22, 2023 | Monday – Friday: 330 – 630PM | Saturday & Sunday: 11AM-6PM. This holiday season, families are invited to take a complimentary photo with Santa Claus himself at Stew Leonard’s. 

See additional events HERE!

Tuesday, December 19 | 10AM-11AM
Stew Leonard’s Norwalk

Selfies with Santa at the Sono Collection

‘Tis the season – 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 take your own photos with Santa for a FREE festive photoshoot.

November 24 – December 24 | Friday, Saturday & Sunday| 12PM–6PM

For additional holiday events at the Sono Collection, click HERE!

A Christmas Carol @ The Downtown Cabaret

It’s the perfect holiday treat for the whole family: a brand new twist on the timeless story of Ebenezer Scrooge and his journey to discover the true meaning of Christmas. Join Tiny Tim, Bob Cratchit, Jacob Marley, Mr. Fezziwig, and many more as past, present, and future collide to teach Scrooge about kindness and generosity in the season of giving.

Shows running Saturdays and Sundays through end of December, and extra shows during Christmas week!

Buy Tickets Today!

Rudolph the Red Nosed Reindeer: The Musical at the Palace

The beloved TV classic RUDOLPH THE RED-NOSED REINDEER soars off the screen and onto the stage this holiday season. 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. Based on the animated television special “Rudolph the Red-Nosed Reindeer” and the stage production directed and conceived by Jeff Frank and First Stage. Script adaptation by Robert Penola. Arrangements by Timothy Splain. Orchestration by William C. White.

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

Winter Market at Lachat Town Farm

The Lachat Winter Market provides a chance to shop locally for gifts in preparation for the winter holidays-or just for fun! Featuring local vendors selling art, clothing, jewelry, housewares, baked goods and other locally produced foods, the market offers a wide range of products-there’s something for everyone. Warm your hands with hot beverages sold at the Lachat Bar (drinks for kids and adults- with proceeds going directly to the farm). Catch up with with friends and neighbors while whittling down your shopping list!

WINTER COAT DRIVE – In the spirit of giving and sharing this Holiday Season, please donate your gentle used or like new winter coats for children and adults to benefit Open Doors a community resource center and homeless shelter in Norwalk whose motto is Shelter | Support | Success. Collection bins will be set up at the Lachat Winter Market on Dec 2nd. Please share your warmth with someone in need!

December 2

Winter Whimsy and Annual Fairfield Tree Lighting

Event Date: Saturday, December 2, 2023
Location: Old Town Hall & Museum Commons
Time: 4:15pm – 7:00pm
Ages: All Ages
Fee:  Free Event!
Sponsored By: Cambridge Health, Cosmetic & Reconstructive Dentistry, Feast & Fettle, KMS Team at Compass Group, Nichols MD, Soccer Shots

Holiday Express Train Show @ Fairfield Museum

Warm up at the Fairfield Museum after the town’s tree lighting ceremony and be one of the first to see the new displays of the Holiday Express Train Show! Young and old alike will delight in the model trains winding around spectacular winter villages and beautiful holiday scenery.

$3 per person, $10 per family

December 2nd
370 Beach Road, Fairfield, CT

Music Man Jr. at The Fairfield Theatre Co

Based on Meredith Willson’s six-time-Tony-Award-winning musical comedy, The Music Man JR. features some of musical theatre’s most iconic songs and a story filled with wit, warmth and good old-fashioned romance. Family entertainment at its best — a bold, brassy show that will have the whole town atwitter!

Presented by Octagon Performance Group, a nonprofit arts education organization based in Fairfield.

December 3rd – 330PM
Buy Tickets HERE

Lachat Farm Wreath Making

All are welcome to join the Weston Garden Club and Lachat Town Farm as they collaborate on an evening of community and creativity at the farm. Design your own custom wreath for the Winter season, using a plentiful selection of bows, baubles and natural materials that will be available for use. Grab your friends, neighbors and family, and join us for a delightful gathering in front of the roaring fire in the new Daniel E. Offutt III Education Center gathering space.

Price includes ($85/pp): wreath, bows, various decor items. Festive nibbles include another amazing charcuterie board by Traci Baker, a dessert selection, coffee and tea. Guests are encouraged to BYOB (beverages and any specific baubles or decor items ).

December 7

A Christmas Carol @ The Wilton Playshop

Back by popular demand, The Wilton Playshop is once again staging a fantastic one-man adaptation of Charles Dickens’ “A Christmas Carol”. The timeless tale of redemption and hope tells the story of Ebenezer Scrooge, a greedy miser who hates Christmas. He is transformed into a caring, kindly person when visited by four ghosts on Christmas Eve: Jacob Marley, and the spirits of Christmas Past, Present, and Future. Patrick R. Spadaccino, who both adapted the show and stars in it, plays twenty-five different roles in the ninety-minute performance and brings each character to life! The show, which was originally presented in 2018 at the Farmington Valley Stage Company in Collinsville, CT, is directed by Scott R. Brill.

December 8th and 9th – 8PM | December 10th – 2PM
Tickets: $30/adults, $25/seniors and students.
For tickets and more information, visit www.wiltonplayshop.org

Greenwich Historical Society Holiday Festival

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

Holiday Happenings & Movie Night

Tickets go on sale November 15t 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

Candy House Workshop @ Fairfield Museum

Celebrate the magic of the season by creating a sweet and colorful candy house with recycled materials and lots of sweet treats!
Space is limited. Registration is required.

$25 per house (includes admission for 1 adult & 1 child to Holiday Express Train Show)

December 16th
370 Beach Road, Fairfield, CT

Christmas Tree Cone Making Class

Children will make yummy Christmas tree cones!
Children will decorate six sugar cones to make their own holiday-themed Christmas tree using festively colored frosting, sprinkles, M&Ms, and other special decorations.
Each child will bring their yummy treats home with them. Parents or caretakers are asked to accompany their child to this class.
$20 per child

Tuesday, December 19 | 10AM-11AM
Stew Leonard’s Norwalk

Greenwich Reindeer Festival

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
Monday – Friday 12pm – 6pm, Saturday 9am – 6pm
Sam Bridge Nursery & Greenhouses
437 North Street, Greenwich, CT 06830

Bronx Zoo Holiday Lights

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

NYBG Holiday Train Show

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

Festival of Lights at Harvest Mood & Orchard

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

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