Festive Holiday Guide - FairfieldMoms


December is almost here and we are in full Holiday mode!  This month we are excited to keep you up to date with all things HOLIDAY that is happening in Fairfield & surrounding towns for you and your family!  We’ve highlighted a TON of events, photos with Santa, Nutcracker performances, Holiday fairs & much, much more!!  Happy Holidays!  More details for each event can be found on our Calendar here!

Breakfast with Santa

Hub & Spoke
November 26th: 9:30am – 11am & 11am – 1pm
Includes breakfast buffet, story time and a special gift for your child from Santa.


The SoNo Collection: Nordstrom
December 3rd: 9am – 11am
Mornings are magical this time of year. We make them extra warm and fuzzy with a delicious holiday-inspired breakfast, Santa visits and photo ops, kids’ activities and merry music


December 3rd-4th, 9th-10th, 17th-18th
Enjoy brunch with the big guy himself!


Fairfield Ludlow High School
December 10th: 10am – 12pm
Santa Claus is coming to town!  This event is open to all Fairfield Families through the courtesy of Fairfield Parks and Rec Department.


Maritime Aquarium
December 17th: 8am – 10am
Members are invited to join us in their pajamas for a breakfast with Santa Claus! Bring your camera … Santa will be available for pictures.


Stew Leonard’s
December 17th: 10am – 11am
Families are invited to have breakfast with Santa and his friends! A buffet-style breakfast of scrambled eggs, pancakes, bacon, sausage, assorted bagels, fruit and donuts, will be served accompanied by coffee and hot cocoa! Each child will be able to decorate a wooden ornament to take home. Limited seating available and registration must be made in advanced on our website

Tree Lighting

Fairfield Annual Tree Lighting
December 10th: 4:15pm – 7pm
Old Town Hall & Museum Commons

The occasion that truly kicks off the holiday season in Fairfield is the annual lighting of the Christmas tree! Gather with your family and countdown at our Annual Tree Lighting on the Town Hall Green starting at 4:15 PM!  Followed by our new Winter Whimsy event taking place on the Fairfield Museum Commons! Winter Whimsy will feature food trucks, a beer (& hot beverage) garden, DJ, Holiday Express Train Show, carriage rides, holiday crafts, pictures with Santa, & petting zoo!  Choirs begin at 4:15 PM | Tree Lighting at 5:00 PM | Winter Whimsy from 5:00 PM – 7:00 PM


Stew Leonard’s
November 29th: 5pm – 6pm
Stew Leonard’s Norwalk store is kicking off the 2022 holiday season with its annual Christmas Tree Lighting celebration. The festivities begin at 5 p.m. with musical entertainment from the Norwalk High 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.


Trumbull Holiday Tree Lighting
December 2nd: 6pm – 7pm
Trumbull Town Hall
Live performances by Madison Middle School Band and the Trumbull Youth Association. Special appearance by Santa!


Wakeman Town Farm Tree Lighting
December 2nd: 4:30pm – 6:30pm
Wakeman Town Farm, WestportIt’s a festive, fun and free event for the whole family, thanks to our sponsor, Freudingman & Billings. Enjoy free sweet treats from The Porch & Sweet P Bakery, and warm up with hot chocolate from The Granola Bar around our roaring bonfire. As is our tradition, we’re featuring a variety of local school musicians playing some Christmas and Chanukkah favorites. Join us as First Selectwoman Jennifer Tooker and Bill Constantino (a Wakeman family member) light up the Wakeman tree to kick off the season and keep a generations-old family tradition alive for the community!  Free and open to the public. This is an outdoor, family friendly event. Dress warmly.


Greenfield Hill Tree Lighting
Greenfield Hill Church
December 4th: 5pm


Easton Tree Lighting
Easton Public Library
December 4th: 5:15pm


Fairfield University Annual Tree Lighting
December 5th: 6:15pm – 7:30pm
Egan Chapel Patio, 1073 North Benson Road, Fairfield
As the most wonderful time of the year descends upon families and friends young and old, Fairfield University will add to the merriment with the annual Tree Lighting Ceremony on Monday, December 5 at 6:15 p.m. outside the Egan Chapel of St. Ignatius of Loyola. The event is free and open to the public. The University will welcome the greater Fairfield community with hot chocolate and cookies to warm spirits. University singing groups, The Bensonians and Sweet Harmony, will perform songs of the season. Lucas and Santa will join the fun for pictures, and there will be a Fairfield Holiday Pop-Up Shop with gift essentials like ornaments.



Menorah Lighting


Pequot Library
December 20th: 6:30pm
Hosted by the Chabad of Fairfield and the Chabad of Westport, the Pequot Library will host a menorah lighting.  This event is open to the public and will feature music by DJ Chaim, swag bags, refreshments and more.


Stew Leonard’s
December 18th: 5pm – 8pm
Stew Leonard’s Norwalk store is celebrating Chanukah, the Festival of Lights, with its 30th annual menorah lighting celebration. The celebration starts with Rabbi Yehoshua Hecht of Beth Israel Chabad of Westport/Norwalk lighting an 18-foot menorah. Following the menorah lighting is a celebration complete with live music, holiday song and dance and complimentary Kosher refreshments and juice. Traditional dreidels and chocolate gelt will be distributed to all



New Years Eve


Stepping Stones Museum
December 31st – 11:30am – 1pm
It will be a rockin’ Noon Year’s Eve at Stepping Stones as Star Factory’s DJ Lou will be in the house to help us say goodbye to 2022 and ring in 2023! Join us in the Multimedia Gallery to dance, sing and have a blast as we watch New Year’s Eve celebrations from around the world on our huge, immersive screen. Be there before noon as we’ll Countdown to Noon with great fanfare just like the grownups get to do 12 hours later. No tickets required for this event and the Multimedia Gallery gate will be open so everyone can participate in the fun!


Photos with Santa

Bass Pro Shop, Bridgeport
November 5th – December 24th
Reserve your spot


Fairview Tree Farm’s Night of Lights
December 2nd – 4th, 9th-11th, 16th-18th | 5pm – 9pm
Join us for a magical night of holiday lights on our first annual Christmas nighttime hayride! A 30-minute tractor pulled wagon will take you through our decorated and lit tree fields and holiday scenes. Visit with Santa, Mrs. Claus, the Grinch, and more! Holiday Spirit throughout our farm! Sit by a cozy bonfire while sipping on tasty treats. Family fun for all ages!
Beginning December 2nd and running select nights through December 18th. Reservations are Required! Children ages 2 and under are FREE! Please arrive 30 minutes prior to your scheduled start time


Holly Days Festival & Market
Westport Museum for History and Culture
25 Avery Place, Westport
December 3rd: 10am – 4pm
This family-friendly event will bring the holiday spirit to downtown Westport. View our gingerbread village of local buildings, listen to Charles Dickens in a live recitation of A Christmas Carol, enjoy the warming fire and some goodies from our partners, and much more. While you shop, purchase your Santa ticket! For $5 per child your visit with Santa includes a candy cane or sticker and professional photographs sent via an email link. Buy your Family level membership today to beat the crowds during the early member hour and receive your photographs for free. While you’re here have a one-of-a-kind hand cut silhouette crafted right before your eyes.


Holiday Caroling Party and Open House
Pequot Library
December 9th: 5pm – 7pm
Join Pequot Library for our signature winter event, full of festive holiday cheer: crafts, choirs, treats, horse-drawn carriage rides, cocoa with Coco Bunny, surprise visitors from the North Pole, and our first-ever holiday market


Sherman Town Green
Santa’s Arrival, Fairfield
November 27th: 10am – 2pm


Santa Sunday at The Beehive
79 Sanford Street, Fairfield
November 27th: 11am – 2pm
We love seeing your kiddos conversing with the big guy – and with your $10 (minimum) donation you can snap a photo with Santa AND join us in raising money for Bridgeport Rescue Mission! Santa’s visit is on us and 100% of your donation goes DIRECTLY to this amazing organization!


St. Nick Comes to Downtown Southport
December 8th : 5pm – 7pm


The SoNo Collection, Norwalk
Selfies with Santa

Fridays: 5pm – 9pm | Saturday – Sunday 11am – 5pm (starts November 25th – December 24th)
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.


Sport Hill Farm, Easton
December 4th: 10am – 2pm
Bring a camera and capture the memories.  Treats and more happening outdoors on the farm!


SENSEsational Santa
December  10th: 9am – 1pm
Rehabilitation Associates, Fairfield
Come to our SENSEational event for a more enjoyable and sensory-friendly experience! Experienced and licensed therapists will assist each child during the event and each family will go home with a holiday photo and a holiday craft!  Choose to take a picture with Santa or in our Winter Wonderland scene!  TO SCHEDULE, please call (203) 423-0525

Holiday Lights, Fairs & Festivals

Holiday Lights

Fantasy of Lights
Lighthouse Point Park, East Haven

  • Hours: SUNDAY – THURSDAY 5pm-9pm  |  Friday & Saturday 5pm – 10pm
  • Admission: Car/Family Van $10  |  Minibus $25  |  Full-size Bus $50

Fantasy of Lights, presented by Goodwill of Southern New England, has become a holiday tradition for thousands of families. Now in its twenty-seventh year, the dazzling nighttime event supports our mission: to enhance employment, educational, social, and recreational opportunities for people with disabilities and other challenges


Wonderland at Roseville
Roseville Road, Fairfield
Opening night November 24th – 5pm



Fairs & Festivals


Holiday Stroll
Mill River Park, Stamford
November 18th – December 24th
Thursdays – Sundays 4pm – 8pm
The All-New holiday stroll returns with an illuminated showcase that brings alive the wonder of the season. This spectacular walk-through experience is designed to capture the hearts of every generation with even more larger-than-life, family-friendly displays, a 30-foot state-of-the-art interactive Christmas Tree, carnival rides, a winter beer garden & so much more!.  Purchase tickets ahead!


Holiday Express Train Show
Fairfield Museum & History Center
Opens December 3rd – and all month long!
Warm up at the Fairfield Museum before or after the town’s tree lighting ceremony and be one of the first to see the new displays at the Grand Opening of the Holiday Express Train Show! Kids and adults alike will delight in the magic of the model trains winding around a winter wonderland of spectacular trees and beautiful holiday scenery. The Museum will be open this evening from 5:00-8:30 pm so that families with young children can be among the first to experience this fun tradition.


Scandinavian Christmas Market
1351 S. Pine Creek Road
December 3rd: 10am – 3pm


Holly Days Festival and Market
Westport Museum for History and Culture
25 Avery Place, Westport
December 3rd: 10am – 4pm
This family-friendly event will bring the holiday spirit to downtown Westport. View our gingerbread village of local buildings, enjoy the warming fire and some pre-packaged goodies from our partners after perusing the offerings of local and regional vendors. And why not get those gifts wrapped at our wrapping station? Gifts from anywhere wrapped for a nominal fee that supports the museum. While you shop, stop and take a quick picture with Santa!


Holiday Market & Tree Lighting
Two Roads Brewing Company, Stratford
December 3rd: 2pm – 8pm
Join us on Saturday December 3rd for our pop- up Holiday Market! Local vendors, each with amazing and unique products, will be stationed around campus in both our Tasting Rooms! In addition to our winter market, we will also be hosting our annual tree lighting ceremony outside in the hop yard!


Popshop Holiday Market
December 3rd: 10am – 3pm
The much anticipated Holiday Market returns for year nine, and it’s the biggest YET! Cross off everyone on your list. This is a FREE event


Winter Market
Lachat Town Farm, Weston
December 3rd: 10am – 2pm
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 Barn Bar (drinks for kids and adults- with proceeds going directly to the farm). Warm your soul with friends and neighbors catching up around the roaring fire pit. Please come dressed for the weather and ready for holiday merriment!


Kid’s Gingerbread House Workshops
Lyman Orchards
December 4th, 17th, 18th: 10am – 11am 
Come out for a crafty, creative confection! Sign the kids up for a Lyman Orchards Gingerbread House Workshop built just for them


Holiday Open House
The Lockwood-Mathews Mansion
December 4th: 12pm – 4pm
The Museum will feature a Holiday Open House with Santa Claus and a special musical performance featuring Music Theatre of Connecticut’s School of Performing Arts. Visitors will also have an opportunity to view the new holiday exhibition, take selfies or memorable family portraits, indulge in refreshments in the Mansion’s Cafe, and enjoy the enchantment of the Museum’s holiday displays


Holiday Market & Tree Lighting
Easton Public Library
December 4th: 2:30pm – 6pm
Please join us for our wonderful community event open to all who are young at heart and want to get into the holiday spirit! Artisans … hot chocolate … crafts … Santa and Ms. Claus … sing-a-long … Barlow Chamber Singers … Tree Lighting! All great!


Fairfield Holiday Shop & Stroll
December 8th: 6pm – 9pm


An Elf’s Journey
Fairfield Library
December 9th: 6:30pm – 8pm
For one epic night, Fairfield Public Library will be turned into the Seven Levels of the Candy Cane Forest.  Your team will travel through the forest in this after-hours Scavenger Hunt to help Buddy the Elf find something very dear. *This is scavenger hunt is like our popular Halloween Time Mystery Night but it’s all treats and no tricks! This event is for individuals in grades 6-12 and their families (or team of friends).  Every individual in your group must register.  There must be a teen (grade 6-12) registered with your group to participate in this event.


Winter Wonderland
Westport PAL Rinks at Longshore
260 Compo Road South, Westport
December 9th: 5pm – 10pm
LivFree & Westport P.A.L. are coming together again to bring you a fun, festive event – Winter Wonderland. Please join us for an evening of ice skating, caroling, a visit from Santa & so much more! All proceeds will benefit LivFree & Westport P.A.L. We will also host a toy drive there that will benefit Al’s Angels!


Candy Cane Farm
Lachat Town Farm, Weston
December 9th – 11th: 4pm – 7:15pm
Welcome to Candy Cane Land, the Premiere farm that grows the world-supply of peppermint candy. However, it looks like the Peppermint Patch’s harvest for the year has disappeared. Guests must set out into the sugar coated wilderness and unlock the magic within to find the missing minted treasure.  Purchase tickets here!


Holiday Caroling Party & Open House
Pequot Library, Southport
December 9th: 5pm – 7pm
Celebrate the holidays with Pequot Library! Join us for a festive evening of  holiday cheer, music, treats, horse drawn carriage rides, and a surprise visit from the North Pole!


Fairfield Museum & History Center
December 10th: 10 – 3:30pm
Choo choo! Build & paint your own wooden model train and create an immersive, wintry landscape. Each workshop session will last 90 minutes.


Annual Winter Wonderland
New Canaan Nature Center
December 17th – 11am – 2pm
Come and be transported into a whole new world as the New Canaan Nature Center transforms into a Winter Wonderland filled with fun and exciting winter holiday activities for the entire family. We hope you will join us to enjoy the warm festive feel the Nature Center puts on this time of year!


Candy House Workshop
Fairfield Museum & History Center
December 17th: 10am – 4pm
Celebrate the magic of the season by creating a sweet and colorful Candy House built with recycled materials and lots of sweet treats! Let your imagination bring to life a holiday scene decorated with gumdrops, peppermints, marshmallows, licorice, and more!


Winter Solstice Celebration
Terrain, Westport
December 21st: 4pm – 6:30pm
Join us in the cafe to welcome the Winter Solstice with seasonal dishes and warming cocktails. Enjoy holiday decor and caroling throughout the night.

Performances, Movies & Concerts

Rudolph The Red-Nosed Reindeer: The Musical
The Palace Theater, Stamford
November 26th: Shows at 2pm and 6pm
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.


The Santa Story
The Downtown Cabaret, Bridgeport
November 26th  – December 30th (Saturday’s and Sunday’s)
We all know who Santa Claus is, but where did he come from? This wildly popular Cabaret original is the heart-warming and hilarious story of a young Christopher Kringle and his journey to become Santa Claus. The perfect blend of music, mayhem, and merriment for the whole family that is sure to have you ringing jingle bells this holiday season.


Holiday Movies at the SHU Community Theater
1420 Post Road, Fairfield
December Showings
Movies: Frozen, Frozen 2, Elf, Santaman, The Polar Express


The Nutcracker by Westport Academy of Dance
December 3rd and 4th
Our annual production of The Nutcracker includes Westport’s Academy of Dance students that are enrolled in our Ballet Program. Junior and Senior Company members dance the leads alongside professional male dancers in their appropriate roles. The Academy’s Nutcracker has become a Westport tradition adding joy throughout the holiday season


Jingle All The Way
Wilton Historical Center
December 4th: 2pm
Join Music on the Hill as they perform favorite holiday carols and winter songs with singers and ringers! Jingle All the Way will take place on Saturday, December 3 from 2:00 – 3:00 outside by the Abbott Barn. Perfect for kids, parents and grandparents, and includes a fun jingle-bell craft. No charge, donations encouraged.


Rockwell Dance Center, A Winter Ballet – Nutcracker
Mertens Theater, Bridgeport
December 10th: 3pm & December 11th: 2pm 


CT Dance School Presents, The Nutcracker
Quick Center for The Arts, Fairfield
December 11th: Shows at 1pm and 4pm


New Paradigm Theatre Company Holiday Show
The Warehouse FTC, Fairfield
December 10th: 8pm |  December 11th: 3pm
Join New Paradigm Theatre Company (NPT) and usher in the holiday season at the Fairfield Theatre Company’s StageOne with spectacular performances! NPT’s annual holiday extravaganza features Broadway and local stars who will perform the annual Holiday-themed show on Saturday December 10th at 8:00pm and Sunday December 11th at 3pm. The holiday show is jam-packed with Broadway dancers, singers, instrumentalists, and “Ms Clauz with a Z”© and her elves. Music Directed by Chris Coogan


The Nutcracker
The Palace Theater, Stamford
December 17th – 18th
A holiday tradition for the whole family, Connecticut Ballet’s magical Nutcracker returns to The Palace!


ROCK4RV Holiday Party
Park City Music Hall
December 17th: 6:30pm – 11pm
ROCK4RV Holiday Concert in memory of Robert (Bob) Vitanza, who succumbed to Creutzfeldt-Jakob Disease (CJD) in 2008. All proceeds fund research grants for the CJD Foundation, Inc., a 501(c)(3) organization committed to supporting individuals affected by this rare and fatal brain disease. Please join us on the path to find a cure!


Chamber Music Concert
Fairfield Museum & History Center
December 18th: 2pm – 3pm


Fairfield High Schools Ring In The Holidays
Warde High School Presents Carillon: Tuesday, December 20th – 6:30pm and 8:30pm
Ludlow High School Presents Candlelight: Thursday, December 22nd – 6:30pm and 8:30pm



We make every effort to ensure the information above is accurate.  However, events are subject to change and we advise you to call ahead and confirm.  

If we are missing any events that should be highlighted, please let us know and we will be sure to add!  Email us at [email protected]

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