Holiday Happenings in Fairfield! | FairfieldMoms


December is 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!

Breakfast with Santa

Connecticut Beardsley Zoo
December 7th, 14th, 21st: 8:30am – 10am
December 8th, 15th, 22nd: 8:30am – 10am
The delicious buffet breakfast includes photo opportunities with Frosty the Snowman, Stripes the Tiger, Thirsty the Penguin, and even Santa and Mrs. Claus.  Tickets are on sale now! Online reservation & pre-payment is required to attend. Event is $20 per person for Zoo Members and $25 per person for non-Members. Children 2 years old and younger are free.


The Klein
December 7th: 9am – 10:45am
Have breakfast & take pictures with Santa & friends! Tickets: $7 per person.  After breakfast, see a show with the whole family!  The Elf Christmas Spectacular runs at 11:30AM & 2:00PM. It’s a whimsical tale of an elf who goes to hilarious lengths to win a talent competition & a spot on Santa’s sleigh on Christmas Eve. Sing along with the cast and meet Santa after the show. This Christmas Classic ran in Boston for 29 years before its well-received debut show at The Klein in 2018! Written & directed by Maureen Hamill. Tickets are $12 for the show and ages 2 & under are free! Show runs 1 hour


Stew Leonard’s
December 14th: 9am – 11am
Families are invited to have breakfast with Santa and his friends Wow the Cow and Cynthia Chick! A buffet-style breakfast of scrambled eggs, pancakes, bacon, sausage, hash browns, mini muffins, assorted bagels and fruit salad will be served. Children age 10 and under are $12.99/each and those age 11 and over (including accompanying parents) are $14.99/each. Children 2 and under are free.  ***Every person attending the breakfast must have a paid ticket or will not be allowed in***


Fairfield Ludlow High School
December 14th: 10am – 12pm
Santa Claus is coming to Town! Gather the family together for a fun breakfast of donuts, bagels, coffee, juice, hot chocolate and more. Get a chance to have the kids visit with Santa and Mrs. Claus and get that perfect Holiday photo. What better way to kick off the season?  This event is sponsored by the Parks & Recreation Department , the Police Athletic League and the Town Youth Council.  A $1 per person donation is requested to benefit a Town Youth Council fundraiser, the Jacky Durrell Memorial Service Award Scholarship. Each year we award at least 2, $1000 scholarships to FHS graduates based on their community service accomplishments.


Hub & Spoke
December 15th: 5pm – 8pm
Supper & Storytime
Join us for a night of wonderment with a visit from Santa! Make your reservations now and enjoy dinner and story-time with the big guy himself! 5 pm seating with story time at 6:30 pm. Full regular menu with themed items added to keep with the festivities!  $5 pp a fun activity for all ages!

Tree Lighting

Westport Annual Tree Lighting
December 5th: 5pm – 6pm
Westport Town Hall


Wakeman Town Farm Tree Lighting
December 6th: 4:30pm – 6pm
Wakeman Town Farm, Westport
It’s a festive, fun and free event for the whole family. In addition to the bonfire, roasting marshmallows and hot cocoa, we’re featuring a variety of local school musicians playing some Christmas and Chanukkah favorites. Join us as we light up the Wakeman tree with fellow Westporters to kick off the season. And…if you’re able, “Be an Angel” and bring an unwrapped gift for the Farm’s Al’s Angels Holiday Toy Collection Box.  Free & open to all!  Tree lighting at 4:45pm!


Fairfield Christmas Tree Lighting
December 6th: 6pm – 7:15pm
Town Hall
Choirs begin at 5:55pm Fairfield Woods, Tomlinson and Roger Ludlowe Middle School, 6:20 Fairfield Warde Chorale Group, 6:45 Fairfield Center Stage, 7pm Tree Lighting – Santa arrives on the Firetruck.  Come celebrate the lighting of the tallest living tree in Connecticut planted by the Daughters of the American Revolution in 1918! The festivities begin at 5:55 pm with the Fairfield Woods, Roger Ludlowe and Tomlinson Middle School Chamber Choir singing songs of the season. The Fairfield Warde Choral Group and the Bridgeport Theatre Company will also be performing. Enjoy some hot chocolate and free glow necklaces compliments of the Town Youth Council.


Trumbull Holiday Tree Lighting
December 6th: 6pm – 7pm
Trumbull Town Hall
Santa will be arriving on the decorated fire truck. Performance by Trumbull Youth Association & Brett Boles.  Music by Madison Middle School Band. Hot Chocolate donated by Maefair Health Care Center & Trumbull Helps. Candy Canes donated by Lisa Valenti, William Raveis Real Estate. Food Pantry Donations accepted that evening on the brick walk. Hot chocolate & candy canes while supplies last


Holiday Tree Lighting
December 7th: 4pm – 6pm
Jesup Hall, Westport
Festive drinks, s’mores and music.  Tree lighting at 5:30pm


Annual Christmas Tree Lighting
December 8th: 5pm – 6pm
Nichols Improvement Association (NIA), Trumbull
Join us for our Annual Tree Lighting & musical performance by the Hillcrest Carolers. Rumor has it that Santa will be taking a break from the North Pole to make a special visit to Nichols.



Menorah Lighting


Beth Israel Chabad Giant Menorah Lighting
December 26th: 5pm
Stew Leonard’s
Beth Israel Chabad of Norwalk/ Westport invites you to Join us for the largest Menorah Lighting in Norwalk. live music, Chanukah gelt, dreidels and more.  Free and open to all.



Photos with Santa

Bass Pro Shop, Bridgeport
Weekdays: 3pm – 8pm.  Starting December 8th – 23rd: 10am – 8pm
Saturdays: 10am – 8pm
Sundays: 10am – 5pm


Stew Leonards, Norwalk
Weekdays: 3pm – 6pm
Weekends: 11am – 6pm


The SoNo Collection, Norwalk
Selfies with Santa

Fridays 5pm – 9pm | Saturdays 12pm – 6pm | Sundays 12pm – 6pm (runs through December 22nd)
Tis the season! If you’re looking for a fun and festive way to celebrate the holiday season, look no further—we’re offering photos with Santa!  Reserve your FastPass today.  Create magical memories, make the holidays special, and take care of those wish lists—all in one place.


Mitchells, Westport
Photos with Santa

December 7th, 14th, 21st: 11am – 1pm
Free & open to the public!


Sensory-Friendly Santa
December 8th: 8:30am – 10:30am
Westfield Trumbull Mall
Westfield Trumbull has partnered with Autism Speaks to host “Sensory-Friendly Santa,” an opportunity for children with Autism and other special needs (and their siblings) to visit with Santa in a more soothing and sensory-friendly environment. During the event families will enjoy a quiet visit with Santa supported by no overhead mall radio or audible music from nearby stores, no long lines, and lower shopper traffic. In order to create a special experience for each family, event tickets are limited and each family must register in advance for a specific 30 min time slot (8:30 – 9:00 AM, 9:00 – 9:30 AM, 9:30 – 10:00 AM, or 10:00- 10:30 AM). Each time slot is available to register for on a first come, first served basis (one ticket per group/family).The Santa Set is located in JCPenney Court on the first floor.


BD Provisions, Fairfield
December 8th: 11am – 3pm
Come meet Santa and take a free photo at this festive event.


Sport Hill Farm, Easton
December 8th: 1pm – 3pm
Admission – Donations of non-expired, non perishable foods to be donated to our friends at The Black Rock Food Pantry


The Pilot House Community Farm
December 8th: 2pm – 7pm
December 15th: 2pm – 7pm
Winter Wonderland
Join us for pictures with Santa, games, Holiday sleigh rides, Christmas tree sale, craft show & food trucks.  Admission $10 per child


Fairfield Social
December 10th: 5pm – 8pm
Join us for a great night with lots of fun with Santa and the elfs.


SENSEsational Santa
December 14th: 8:30am – 12pm
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!  COST: $5 per photo.  TO SCHEDULE, please call (203)384-8681, ext 562, by Thursday, December 5th


Jones Family Farm, Shelton
December 21st & 22nd: 10am – 4pm
Santa vists the farm

Holiday Fairs & Festivals

Holiday Shop & Stroll
December 5th: 6pm – 9pm
Start the night at FairfieldMoms’ Happy Hour at Malibu Taco from 5pm – 7pm!  Shop downtown from 6pm – 9pm, and then meet us at our After Party at The Chelsea from 8pm on.  Drinks & small bite specials at both locations.  Be sure to mention FairfieldMoms Shop & Stroll!  #shoplocal #eatlocal


Holiday Gift Fair
December 5th: 5pm – 8:30pm
Brooklawn Country Club
Many great local artisans, vendors & cash bar


Fairfield Christmas Tree Festival
December 6th: 10am – 7pm
December 7th: 10am – 5pm

December 8th: 10am – 4pm
Burr Mansion
Fairfield Christmas Tree Festival is a wonderful annual celebration of the season featuring designer curated rooms and a variety of special events including Camp Hip Hop (Dec.6), Casino Under the Stars (Dec.7) and the Nutcracker “Sweet” Tea (Dec.8). Proceeds from this year’s festival will directly benefit Camp HOPE, New England’s first trauma-informed camp and mentoring program for children impacted by domestic and sexual violence.  Admission $10 adults / $8 Seniors  & Children over 3.


Holiday Express Train Show
December 6th: 5pm – 8pm (opening night)
Monday-Thursday: 10am-1pm
Fridays: 10am-7pm
Saturdays & Sundays: 10am-4pm
December 23, 24, 26, 30 and 31: 10am-4pm
Closed Christmas Day and New Year’s Day

Fairfield Museum & History Center
A Fairfield tradition returns with exciting programs and activities for visitors for all ages! View the display of model trains and the elaborate scenery as the trains travel through villages, up and down mountainsides, and across snowy fields, mesmerizing all who come to see them. Train-themed items and other holiday gifts are on sale in the Museum Shop, and fun events, including story times and candy house workshops, take place all month long. Opening Night on December 6th features treats, cider and reduced-price admission.


Three Kings Bazaar
December 6th: 5:30pm – 8:30pm
December 7th: 10am – 3pm
First Church Congregational, 148 Beach Road
Friday evening there will be a Christmas Carol Sing with hot dogs and hot chocolate. On Saturday there will be a soup and sandwich luncheon, and on both days, shoppers can enjoy browsing the new and nearly new items in Mrs. Claus’s attic, yummy homemade baked goods, wonderful books for all ages, beautiful jewelry, and crafts. This year’s silent auction features tickets to many theater events: two tickets to the Broadway show “Come From Away” with overnight accommodations and spending money, two tickets for the Downtown Cabaret, two for an adult show at the Klein, two for a kids’ show at the Klein, and two for the Westport Country Playhouse!


Celtic Christmas Fair
December 7th: 9am – 3pm
Gaelic-American Club
Celtic Christmas Fair has a great selection of Irish vendors and unique crafters so you can do all you holiday shopping in one place. Bring the children & grandchildren to have their photo taken with Santa in front of the GAC’s beautiful stone hearth. And don’t forget the Lenihan School of Irish Dance will be serving lunch in the Pub.


Scandinavian Club Holiday Fair
December 7th: 10am – 3pm
Scandinavian Club
Come celebrate the Holiday season with wonderful shopping and delicious food at the Scandinavian Club’s Annual Holiday Fair. There will be vendors, Nordic gifts & food, specialty & handmade items, wonderful baked goods, holiday plants, a café, raffle prizes, entertainment, and a visit from Santa!


Stratfield Village Holiday House Tour
December 7th: 11am – 4pm
This is the second year of the Stratfield Village Association (SVA) Holiday House Tour. The tour will showcase five houses of varied architectural styles decorated for the holidays and will be held on Saturday, December 7th, from 11 am to 4 pm. The houses on the tour will remain a secret until tickets are picked up on December 7th.  While the tour is a fun, festive way to kick-off the holiday season, it is also a fundraiser for the SVA to support building community through neighborhood beautification efforts, community activities, and historical preservation.


St. Pius X Christmas Bazaar
December 7th: 11am – 5pm
St. Pius X Catholic Church
All are welcome for a festive and fun day of holiday shopping and merriment!


Holiday Open House
December 7th: 11am – 3pm
Fairfield University Bookstore
It’s our eighth annual Holiday Open House! Join us for Author Signings, Live Music, Raffle Prizes, and more! A few higlights: Silly-Dilly Sing-A-Long with author Alan Katz, Santa arrives via fire truck, Meet the Grinch at the Grinch Storytime!


Touch a Truck
December 7th: 11am – 2pm
Trumbull Town Hall
Bring an unwrapped toy!  Visit with Santa, Face Painting, Food for the whole family – donated by Vazzy’s


Cookies & Cocoa
December 7th: 11am – 2pm
Nordstrom, The SoNo Collection, Norwalk
Come in for a fun-filled event featuring cookies, hot chocolate, and a festive kids’ station. While you’re here, enjoy personalized services -and we’ll wrap your Nordstrom Purchases for free!


Holiday Market
December 7th: 12pm – 4pm
Lachat Town Farm, Weston
This event will be a chance to shop locally for gifts in preparation for the winter holidays. There will be vendors both in the farm house and barn (with space heaters at the ready). We will have a fire pit and warm beverages for kids and adults with proceeds going directly to the farm. There will be both live music by the Keith Cooper and Trish Radil Duo and caroling by Weston’s own Girl Scouts. A few food trucks will be available to serve a warm meal to our visitors. We will have a children’s craft for gifting. Weston’s Boy Scouts will will be on site to sell Christmas trees and wreaths. Visitors should come dressed for the weather and ready for holiday merriment!


Christmas in The Mansion
December 7th: 6:30pm – 9:30pm
December 8th: 12pm – 5pm
Lauralton Hall, Milford
Celebrate the joy of the holiday season at Christmas in the Mansion! Lauralton Hall’s Milford campus (listed on the State and National Registers of Historic Places) is transformed into a “Showcase of the Season” featuring more than 65 pop-up specialty boutiques offering upscale handcrafted items, home décor, jewelry, clothing, accessories, and more.  Shop early at our Preview Party Saturday, December 7, 6:30-9:30 p.m. (advance tickets only). Enjoy hors d’oeuvres and a buffet dinner with fare provided by Fitzgerald’s Fine Catering of Fairfield, beer and wine, desserts, Christmas music performed by Lauralton student vocal ensembles, raffles, and more.  On Sunday, December 8 from noon to 5:00 pm, Christmas in the Mansion opens to the community. Tickets are available at the door for $10. (Admission is free for children aged 12 and under.) Shop and stroll through our decorated Mansion and hallways, visit Santa’s Workshop, and enjoy treats and lunch from the Food Court. All profits from Christmas in the Mansion support Lauralton student scholarships and programming.


Frozen Jr. 
December 8th: 1pm. 3:30pm, 6pm
December 13th: 6pm, 8pm
December 14th: 1pm, 3:30pm. 6pm
December 15th: 1pm. 3:30pm
Broadway Method Academy
A story of true love and acceptance between sisters, Frozen JR. expands upon the emotional relationship and journey between Princesses Anna and Elsa. When faced with danger, the two discover their hidden potential and the powerful bond of sisterhood. With a cast of beloved characters and loaded with magic, adventure, and plenty of humor, Frozen JR. is sure to thaw even the coldest heart!.  Tickets $15.  All performances held at the BMA studio theater. Frozen runtime is 60 minutes and is appropriate for ages 4 & up.


Holiday Kid’s Party
December 8th: 2pm – 4pm
Nichols Improvement Association (NIA), Trumbull
Join us for a Pre-Tree Lighting Holiday Kid’s Party. We will have holiday themed activities, games, snacks & drinks.  Come for the kid’s party … Stay for the Tree Lighting!  Free for NIA Families, $10 donation for non-NIA families.


LivFree’s Winter Wonderland
December 8th: 5pm – 8pm
Westport PAL Rink at Longshore
Come get into the holiday spirit with LivFree!! Join us for a special night out with ice skating, and appearance from Santa, Holiday carols from Greens Farms Academy, and a camp fire with the Westport Fire Department.We will also be collecting toys for our good friends at Al’s Angels. Iceskating suggested donation of $12 for kids and $15 for adults. ALL PROCEEDS from the event will go towards Livfree’s mission of providing hope to children battling cancer.


Stew’s Christmas Tree Hunt
December 11th: 4pm – 5pm
Stew Leonard’s, Norwalk
Children age 12 and under are invited to visit the several Christmas trees that will be set up throughout Stew Leonard’s Norwalk store and to pick a special ornament off each tree. After the last tree, children will turn in their ornaments for Christmas-themed treats and prizes!  The grand prize winner will receive a personal visit at Stew Leonard’s in Norwalk with Santa Claus himself, where he’ll read a special Christmas book and enjoy milk and cookies with the winner and their friends (limited to a group of 10 children).  Santa Claus, Wow the Cow and Cynthia Chick will be available for picture taking at the event as well.


Small to Tall Jingle Mingle
December 12th: 4:30pm – 8:30pm
Small to Tall Preschool
A shopping event of local vendors for unique holiday presents, pictures with Santa (5:00-5:45 & 7-7:45), kids korner activities, businesses supporting businesses, raffle prizes & more!


Southport Christmas Walk
December 12th: 5pm
Downtown Southport


Holiday Shopping Night
December 12th: 7pm – 9pm
The Pilot House, 240 Colony Street
Still need to do some holiday shopping?  Come enjoy some cheese and champagne while you shop for hand-poured candles, holiday decor, dog treats and so much more!


Holiday Caroling Party
December 13th: 5pm – 7pm
Pequot Library
Celebrate the holidays with Pequot Library’s traditional family-fun event!  Take a horse-drawn carriage ride through Southport Village.  Decorate cookies.  Make a pine cone bird feeder and other seasonal crafts. Listen to Fairfield Country Day School’s Pinstripes (a cappella group) and Bell Choir, St Thomas Aquinas Choir, and GFA Beachside Express.  Sing carols around the bonfire on the Great Lawn.  Free and open to the public


Holiday Fest
December 14th: 9am – 5:30pm
Outdoor Design
Enjoy some Holiday Cheer!  Christmas Trees, Wreaths,Caroling and Treats.  Stay warm sitting by one of our fire pits.  Custom Window Boxes and Containers.  Unique Holiday Greenery.  Specialty Gifts and Workshops. Snowglobe craft for Kids


Sip & Shop Holiday Market
December 14th: 9am – 1pm
Saugatuck Rowing Club, Westport
Support local artisans and merchants.


JWC’s A Visit to Santa’s House
December 14th: 10am – 4pm
December 15h: 10am – 2pm
Burr Mansion
Personal visit with Santa Claus, story time with Mrs Claus, Live Entertainment, Craft Room and Face Painting, Holiday Village Train room, Savory & Sweet treats @Nutcracker Cafe, Raffle Baskets & More.  $7 in advance | $10 at the door. Children under 2 admitted FREE


Winter Wonderland
December 14th: 11am – 2pm
New Canaan Nature Center
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 seasonal activities for the entire family. Festivities include visits with Santa (from 11:30am-2pm), horse-drawn wagon rides ($5/person), holiday trains, campfire with chestnuts & marshmallow roasting, our annual gingerbread house creation contest, caroling with the Bojanglers of CT, and so much more! Tickets: Members: $10/child | Non-Members: $15/child | Adults & Children Under 2: FREE


Build a Gingerbread House
December 14th: 2pm
Fairfield Woods Library
Bring the family to celebrate the holidays by making a candy-covered gingerbread house out of graham crackers and a wonderful assortment of colorful candies and icing! Is it more fun to build or to eat a gingerbread house? Join us and find out! For children of all ages with a parent/caregiver.


Performances & Concerts

Saturday Shows: 12pm – 2:30pm
Sunday Shows: 2pm
Downtown Cabaret Theater, Bridgeport
An all-new musical version of the classic holiday tale!  The iconic reindeer is flying to DCT! He may be a little different, but when a snowstorm threatens to cancel Santa’s annual flight, Rudolph with his nose so bright is the only one who can guide Santa’s sleigh (tonight). Round up the family for a heart-warming holiday adventure about friendship, perseverance, and celebrating our differences! *November 16 – December 29*


Natalie MacMaster & Donnell Leahy: A Celtic Family Christmas
December 5th: 8pm
Quick Center for The Arts
The perfect family event for the holidays! Join the Quick for a special holiday performance by husband-and-wife duo Natalie MacMaster and Donnell Leahy, the award-winning fiddle virtuosos.  Accompanied by an incredible array of talented musicians – and their children – A Celtic Family Christmas includes a lineup of familiar Christmas songs intermingled with classic Celtic tunes.


Camp Hip Hop
December 6th: 5pm – 7pm
Burr Mansion
A family fun night featuring Double Up Dance Studio, Dinner, Dancing and a visit by Santa, Stroll to the Town Tree Lighting.


Holiday Glee!  Open Mike & Karaoke
December 6th: 5pm – 8pm
Fairfield University Bookstore
Bring the whole family for an old-fashioned sing-along and family open mic night! Sign up to sing and receive 20% off your Starbucks favorite item! Anyone can sign up at 5 PM. Performances begin at 5:30 PM. We’re looking forward to a fun musical evening!


The Elf Christmas Spectacular
December 7th: 11:30am & 2pm
The Klein, 910 Fairfield Avenue, Bridgeport
The Elf Christmas Spectacular is a whimsical tale of an elf who goes to hilarious lengths to win a talent competition & a spot on Santa’s sleigh on Christmas Eve. Sing along with the cast and meet Santa after the show. This Christmas Classic ran in Boston for 29 years before its well-received debut show at The Klein in 2018! Written & directed by Maureen Hamill. Tickets are $12 for the show and ages 2 & under are free! Show runs 1 hour.


Grinch Storytime
December 7th: 2pm
Fairfield University Bookstore
A very special guest arrives for his very own HOW THE GRINCH STOLE CHRISTMAS storytime during our Holiday Open House! Join us to share the classic tale, and meet folks from Fairfield/Trumbull School of Music! And you can even take a selfie with the Grinch himself! All kids age 3 and up are invited.


The Nutcracker “Sweet Tea”
December 8th: 1pm – 3pm
Burr Mansion
Featuring a performance by The CT Dance School! Tasty tea, delicious finger food and Scumptious Sweets. $40 per adult, $20 per child (children under 3 are free)


Fairfield County Children’s Choir
December 8th: 3pm – 5pm
The Klein
Fairfield County Children’s Choir kicks off its 25th Anniversary Season, bringing extra sparkle to the holidays, with The Best of the FCCC. The concert features seasonal favorites from a wide variety of composers. There’s something for everyone! The concert opens with a medley of One Voice; Clear Water, and For Unto Us a Child is Born, in which the children’s bright voices will quickly warm hearts and enkindle the festive spirit. Traditional tunes such as Go Tell It On The Mountain and Do You Hear What I Hear? will keep the joyous crescendo rising, as will global holiday offerings, Ocho Kandelikas and S’vivon. To round out the evening, a rousing rendition of Let it Snow! Let it Snow! will have everyone looking forward to winter’s first flakes, no matter the temperature!


Nutcracker Night
December 13th: 6pm – 8pm
Burr Mansion
Special extended performance of The Nutcracker.  Complimentary cookies & cocoa.  Nutcracker Cafe.  Photos with dancers available after the performance


The Nutcracker
December 14th: 2pm
December 15th: 1pm
The Klein
The Academy of New England Ballet Company presents Tchaikovsky’s holiday favorite, The Nutcracker.  This magical performance is perfect for all ages, featuring collaborative choreography from talented professionals and Special Guest Principal Dancers from around the world!  Tickets: $50, $40, $30, $20


Music with a Mission
December 14th: 7pm
First Presbyterian Church, Fairfield
You are invited to an evening of Christmas and classical musical selections featuring violinist Juliana Sharp. Donations support the Ghana Maternity Ward Project. Reception immediately following the performance.


The Connecticut Dance School – The Nutcracker
December 15th: 1pm and 4pm
The Quick Center for The Arts
Connecticut Dance School presents its annual Nutcracker production with two magical performances on Sunday, December 15, 2019 at 1pm and 4pm. Featuring more than 170 dancers, this timeless tradition combines original choreography, elegant costumes and classic sets. CDS’ Nutcracker performances are a true example of ballet as theater and are a perfect way for the entire family to enjoy the season.


The Carillon Holiday Concert
December 17th: 6:30pm & 8:30pm
Fairfield Warde High School


Fireside Tales
December 17th: 7:15pm
Pequot Library
Fathers and their children (ages 3+) can relax in front of the Library’s Reading Room fireplace and enjoy a bedtime story with children’s librarians. Kids and adults can wear pajamas and make popcorn in the fireplace.  Free and open to the public. No registration required.


Candlelight Holiday Concert
December 19th: 6:30pm & 8:30pm
Fairfield Ludlowe High School


A Christmas Carol Experience
December 20th & 27th: 6:30pm & 8:30pm
December 21st & 28th: 12pm, 2pm, 6pm & 8pm
December 22nd & 29th: 12pm, 2pm, & 4pm
December 26th: 6:30pm & 8:30pm
Burr Mansion
A Christmas Carol Experience,” a new adaptation of the Dickens classic, will be an immersive theatrical experience that will take the audience through the many rooms of the historic Burr Mansion as they follow Ebeneezer Scrooge and the Three Ghosts on their journey. The evening will also feature a choir singing carols and dancing at Fezziwig’s party.  This one-hour-long version will be limited to 32 guests per show, and promises to be a unique, intimate, and unforgettable experience.  Tickets, which also include figgy pudding and hot cider served during the play, are $35 for adults and teens (13+), and a limited # of lower-priced tickets ($20) will be allocated for each performance for children 12 and under. Patrons 21+ have the option to ‘spike’ their cider with rum or whiskey for an additional $5.


Connecticut Ballet’s The Nutcracker
December 21st: 2pm & 6pm
December 22nd: 1pm & 5pm
The Palace Theater, Stamford
Connecticut Ballet’s annual production is a staple of holiday entertainment in our region.  Come early and do some holiday shopping at the Nutcracker Holiday Boutique or stay afterwards to meet the guest stars in the lobby.


Parent's Night Out

Tree Lighting & Winter Market
December 7th: 2pm – 9pm
Two Roads Brewing Company, Stratford
Tree Lighting: The Two Roads tree lighting will place outside in our Hop Yard from 4:00 PM – 9:00 PM with the lighting taking place at 6:00 pm! Bundle up and join us outside for music, bonfire, holiday cheer + holiday beer!
Winter Market: The Two Roads Winter Market will take place in our Vault Room! The Market is the perfect place to kick off your holiday shopping and find the perfect gift! With 12+ vendors setting up from 2:00 PM – 8:00 PM stop by the Two Roads Vault Room (event room) to check them all out! Purchase the perfect gift while at the market? You could win a special Two Roads Prize! When any customer purchases something from one of our Winter Market vendors they will give you a raffle ticket to fill out with your name + email, Saturday evening a ticket will be pulled to determine a winner (you do not need to be present to win)!
Area Two: Swell Souls will be popping-up at Area Two from 2-8pm! Stop by, grab a beer, and check out their laid back and tie dye clothing!
The Tasting Room will be open from 12:00 PM – 9:00 PM. The Tasting Room(s), Winter Market and Tree Lighting Event are 21+ ONLY, no children, infants or toddlers! Dogs allowed outside, on the Hop Yard ONLY


Christmasquerade Ball
December 7th: 6pm – 9pm
St. Paul’s Episcopal Church, Fairfield
Join us for a wonderful evening of hors d’oeuvres, drinks, fellowship, and Live & Silent Auctions! Dress is festive and masks are a must. Tickets are $25 per person (21+) and can be purchased on Eventbrite or by mailing a check to St. Paul’s. Masks can be added for an additional $5 and will also be available at the door. Auction offerings include reserved pews on Christmas Eve and Easter, breakfast on the Rectory porch at the Memorial Day Parade, theater tickets, original paintings, a Murder Mystery party, a variety of gift baskets, and much more.


Casino Under The Stars
December 7th: 7pm – 11pm
Burr Mansion
Enjoy an exciting evening with BlackJack, Poker, Crabs, and Roulette! Gourmet food stations, open bar, DJ and exciting auction items. 21+ only.
“Elves” level $125 pp – 200 chips
“Santas” level $200 pp – 300 chips
“Angles” level $300 pp – 400 chips


Dueling Pianos
December 7th: 8pm
Penfield Pavilion
A Night of Two Legends – Elton John & Billy Joel


Holiday Trivia Night
December 12th: 7pm – 10pm
Burr Mansion
21+ | Trivia game throughout the night | Special performance by Exit 46 | Cash bar (beer and wine) | Sweet & savory snacks for sale





New Years Eve Celebrations

First Light Festival
December 31st: 4pm – 10pm
Westport Museum for History & Culture
Join Westport Museum for a night of family fun on New Year’s Eve for events at the museum and around town. The 2nd Annual First Light Festival celebrates the dawning of the New Year and will include many of the beloved activities that Westporters and visitors have enjoyed in years past.  Horse-drawn carriage rides | Face painting | Tarot Readings | A warming fire | Live music by Verbatim | Star gazing with Westport Astronomy Club | Henna Tatoos | Ballroom Dancing


New Year’s Eve Comedy Night
December 31st: 8pm and 10:30pm
Penfield Pavilion
Fairfield Parks & Recreation and Fairfield Comedy Club are ringing in the New Year with Big Laughs! Join us for our Special New Year’s Eve Comedy Event featuring the one, the only… Chuck Nice!

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!

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