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

Pinstripes
December 4th-5th, 11th – 12th, 18th – 19th: 10am – 2pm
Snap a picture with Santa while enjoying your favorite brunch menu items at Pinstripes.  Kids will also enjoy the Reindeer Waffle.

 

Fairfield Ludlow High School
December 11th: 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 and 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 11th: 9am – 11am & 11am – 1pm
Includes breakfast buffet, story time and a special gift for your child from Santa.

Tree Lighting

Fairfield Annual Tree Lighting
December 3rd: 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!  Enjoy some hot chocolate and free glow necklaces compliments of the Town Youth Council.

 

Trumbull Holiday Tree Lighting
December 3rd: 6pm – 7pm
Trumbull Town Hall
Live performances and free refreshments!

 

Westport Annual Tree Lighting
December 3rd: 5pm – 6pm
Westport Town Hall

 

Wakeman Town Farm Tree Lighting
December 3rd: 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 we will enjoy sweet treats from The Porch and Sweet P Bakery and hot chocolate from The Granola Bar and Starbucks.  We’re featuring a variety of local school musicians playing Christmas and Chanukah favorites.  Free & open to all!  Tree lighting at 4:45pm!

 

Fairfield University Annual Tree Lighting
December 6th: 6:16pm
Egan Chapel Patio, 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 6 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. The Student Alumni Association will be on hand to collect donations for the Teddy Bears with Love Drive. Bring a new teddy bear with the tags on, to be donated to local hospitals.

Photos with Santa

Bass Pro Shop, Bridgeport
November 6th – December 24th
Reserve your spot

 

CT Beardsley Zoo
December 4th – 5th, 11th – 12th, 18th – 19th
Holiday Happenings
This year, the Zoo is pairing up with Oliver’s Pajama Project to bring pajamas to underserved communities throughout the state as well as offering three fun weekends of Holiday Happenings. Oliver Koenig-Paquin is a young boy whose dream is to make sure every boy and girl has a pair of new pajamas to keep them warm and cozy at night. Throughout the holiday season, the Zoo will be collecting pajamas at the front gate: all ages and sizes needed!  On December 4-5, December 11-12 and December 18-19, the Zoo will provide festive holiday fare in the Elf Kitchen, featuring hot chocolate, gingerbread, sugar cookies, savory soups, and other festive holiday specialties. Santa’s Sleigh will be set up for Family Photos. Take a stroll through the Zoo and enjoy special crafts and activities with the children, including story times and two appearances each weekend day by a magician. Thirty wreaths from Wreaths Across America can be found around Zoo grounds, to remember fallen U.S. veterans and honor those who serve.  On Saturday, Dec 4 and Saturday, Dec 18, the Zoo will hold a Pajama Parade with Frosty the Snowman, Stripes the Tiger, and Thirsty the Penguin marching alongside Grand Marshal Oliver, founder of Oliver’s Pajama Project. We encourage guests to wear pajamas and bring pajamas to the parade, then take a family holiday pajama photo!

 

Jingle Bell Rock & Outdoor Winter Market
Westport Museum for History and Culture
25 Avery Place, Westport
December 4th: 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!

 

Southport
St. Nick Comes to Downtown Southport
December 9th: 5pm – 6pm

 

Sherman Town Green
Santa’s Arrival, Fairfield
November 28th: 10am – 2pm

 

Santa Sunday at The Beehive
79 Sanford Street, Fairfield
November 28th: 10am – 2pm

 

The SoNo Collection, Norwalk
Selfies with Santa

Fridays – Sundays 12pm – 4pm, 5pm – 7pm (runs through December 20th)
What’s that sound?  Santa’s in town!  The holidays wouldn’t be complete without a visit to the North Pole, so make this holiday unforgettable and take pictures with St. Nick!  Location – Level 3 near CAMP

 

Sport Hill Farm, Easton
December 5th: 11:30am – 2:30pm
Bring a camera and capture the memories.  Treats and more happening outdoors on the farm!

 

SENSEsational Santa
December 4th: 9am – 5pm
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

 

Holiday Lights Spectacular
Hartford Healthcare Amphitheater, Bridgeport
Hours: Sundays – Thursdays: 5pm – 10pm | Fridays and Saturdays 5pm – midnight
Order tickets here!

 

The DRIVE-THRU HOLIDAY LIGHTS SPECTACULAR is running now through January 2nd at the Hartford HealthCare Amphitheater in Bridgeport! One ticket gets you a magical experience for a carload of friends and family! Buy your ticket and go at your own convenience! Sun -Thu 5pm-10pm, Fri & Sat 5pm-midnight! A magical holiday light show  from the comfort of your car as you wind around and through the Amp on a one-mile route of over 2.5 million magnificent lights and lasers! At every turn, the path is overflowing with magnificent holiday displays that bring your favorite holiday themes and characters to life!  Get your carload ticket to the ONLY holiday light show in Fairfield County! Every car also gets over $140 worth of FREE COUPON GIVEAWAYS!

 

 

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

 

 

Fairs & Festivals

 

Holiday Stroll
Mill River Park, Stamford
Thursdays – Sundays 5pm – 10pm
Holiday Stroll is a new holiday tradition located at Mill River Park in Downtown Stamford, CT. A stroll through a festive, dazzling word of larger than life holiday light displays. After strolling enjoy our Holiday Village featuring a state-of-the-art Christmas Tree, holiday music, tasty food vendors, and the Half Full winter beer garden.  Purchase tickets ahead!

 

Santa’s Arrival
Sherman Town Green, Fairfield
November 28th 10am – 2pm

 

Holiday Movies at the SHU Community Theater
1420 Post Road, Fairfield
December Showings
Movies: Home for the Holidays, Frozen, It’s a Wonderful Life, Frozen 2, Christmas in Connecticut, The Santa Clause, White Christmas, Elf, The Polar Express, A Christmas Story, and Gremlins

 

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.

 

19th Annual Lamplight Stroll
Downtown Milford
December 3rd: 5pm – 9pm
Mark your calendars for Milford’s classic New England tradition – the Lamplight Stroll is a charming holiday event and unique shopping experience for the whole family. Enjoy horse and carriage rides around the twinkling Green, yuletide carolers, and of course, a visit from Santa himself! And, check off your list with unique gifts in participating downtown businesses, who welcome with festive refreshments, specials, and holiday cheer!  Come make holiday magic!

 

Three Kings Bazaar
First Church Congregational
148 Beach Road, Fairfield
December 3rd: 6pm – 8pm

 

1st Annual Sip n’ Shop
Newtown Community Center
8 Simpson Street, Newtown
December 3rd: 6:30pm – 9:30pm

 

Holiday Happenings
Connecticut Beardsley Zoo
December 4th-5th, 11th – 12th, 18th – 19th
This year, the Zoo is pairing up with Oliver’s Pajama Project to bring pajamas to underserved communities throughout the state as well as offering three fun weekends of Holiday Happenings. Oliver Koenig-Paquin is a young boy whose dream is to make sure every boy and girl has a pair of new pajamas to keep them warm and cozy at night. Throughout the holiday season, the Zoo will be collecting pajamas at the front gate: all ages and sizes needed! On December 4-5, December 11-12 and December 18-19, the Zoo will provide festive holiday fare in the Elf Kitchen, featuring hot chocolate, gingerbread, sugar cookies, savory soups, and other festive holiday specialties. Santa’s Sleigh will be set up for Family Photos. Take a stroll through the Zoo and enjoy special crafts and activities with the children, including story times and two appearances each weekend day by a magician. Thirty wreaths from Wreaths Across America can be found around Zoo grounds, to remember fallen U.S. veterans and honor thoswho serve. On Saturday, Dec 4 and Saturday, Dec 18, the Zoo will hold a Pajama Parade with Frosty the Snowman, Stripes the Tiger, and Thirsty the Penguin marching alongside Grand Marshal Oliver, founder of Oliver’s Pajama Project. We encourage guests to wear pajamas and bring pajamas to the parade, then take a family holiday pajama photo!

 

Scandinavian Christmas Market
1351 S. Pine Creek Road
December 4th: 10am – 3pm

 

Jingle Bell Rock & Outdoor Winter Market
Westport Museum for History and Culture
25 Avery Place, Westport
December 4th: 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!

 

Winter FunFest
Westport Country Playhouse
December 4th: 11am – 2pm
Winter Fun for the Whole Family! We are pleased to announce the first community event conceived, organized, and run by our Playhouse Youth Council, a group of engaged local high school students. Bring the family to a day of games, story readings, and holiday cheer — fun for every generation! 100% of the net proceeds from ticket sales and pictures with Santa will go directly to Homes with Hope, a Westport-based organization dedicated to ending homelessness in Fairfield County. Keep your tummies warm with hot drinks while you wait to have your photo taken with Santa. Fuel up on festive snacks (and candy) for the music, scavenger hunt, winter crafts and so much more! Proof of vaccination is required for attendees aged 18 and up. Masks are required for all aged 2–18. Snowdate: December 18, 11AM–2PM

 

Winter Market & Tree Lighting
Two Roads Brewing Company, Stratford
December 4th: 2pm – 8pm
Join us on Saturday December 4th 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! This is a FREE event- no tickets needed! The Tasting Room and pop-up events are 21+ ONLY, no children, infants or toddlers! No Dogs Allowed!

 

Winter Wonderland
Westport PAL Rinks at Longshore
260 Compo Road South, Westport
December 4th: 4pm – 9pm
Al’s Angels, LivFree & Westport P.A.L. are coming together 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 children fighting cancer and Westport P.A.L.  Event begins at 4pm – Ice Skating to begin at 5 pm. The event is free to attend – Ice Skating is $20 for Adults/ $15 for Kids

 

Newtown Holiday Festival
Main Street, Newtown
December 5th: 11am – 4pm

 

St. Nick Comes to Southport
Downtown Southport
December 9th: 5pm – 8pm

 

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

 

Holiday Caroling Party & Open House
Pequot Library, Southport
December 10th: 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!

 

Storytime with Santa & Elf
Connecticut Trolley Museum
58 North Rad, East Windsor
December 11th and 12th: 9am – 3pm
This unique daytime holiday program has been specially designed to provide an outstanding and festive holiday experience for families with children. Visitors will enjoy a ride in a decorated vintage trolley car where Santa will visit with each child. Also, while on board Santa’s elf will read a story. During the trolley ride and story, children are given a holiday craft to make.  Following the trolley ride, guests will head to the Visitors Center which has been transformed into a Winter Wonderland with multiple model train layouts and holiday lights galore. Admission prices are $25 per person/per seat (any ages), half off for Museum Members and all ticket sales must be made in advance. There will be no refunds on tickets! Storytime Trolley with Santa & Elf is held Rain or Shine

 

 

Holiday Market at Shaggy Coos
53 Center Road, Easton
December 11th: 10am – 3pm

 

Build a Train
Fairfield Museum & History Center
December 11th: 10am – 4pm
Choo choo! Have you ever wanted to build your very own train? Now is your chance to assemble and paint a wooden model train. You can also create your own immersive, wintry landscapes for your train. $8 per adult, $5 per child, includes museum admission.

 

Shop & Stroll to Music in Town
Downtown Southport
December 11th: 10am – 5pm

 

14th Annual Winter Wonderland
New Canaan Nature Center
December 11th – 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 seasonal activities for the entire family. Festivities include visits with Santa (from 11:30am-2pm), holiday model trains, campfire with marshmallow roasting, cookie decorating, holiday music, crafts & games, and so much more! Members: $10/person. Non-Members: $15/person

 

Winter Carnival
Chester Hill Farm
55 Old Dairy Road, Trumbull
December 12th: 1pm – 4pm

 

Carol Lights
Trinity Church, Southport
December 12th: 4pm – 6pm

 

Polar Express Pajama Party
Newtown Community Center, Newtown
December 12th: 4:30pm – 6:30pm

 

Candy House Workshop
Fairfield Museum & History Center
December 18th: 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!

Performances, Movies & Concerts

Holiday Movies at the SHU Community Theater
1420 Post Road, Fairfield
December Showings
Movies: Home for the Holidays, Frozen, It’s a Wonderful Life, Frozen 2, Christmas in Connecticut, The Santa Clause, White Christmas, Elf, The Polar Express, A Christmas Story, and Gremlins

 

The Polar Express 4D Experience
The Maritime Aquarium, Norwalk
Opens November 26th – January 2nd
Watch “The Polar Express 4D Experience,” a fun condensed version of the Warner Bros. film where you view the movie in 3D, and experience special sensory in-theater effects like snow, wind, the aroma of hot cocoa, and more.

 

Rudolph The Red-Nosed Reindeer: The Musical
The Palace Theater, Stamford
November 27th: 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
December 4th – December 30th (Saturday’s and Sunday’s)

 

Fairfield University Glee Club Christmas Concert
Quick Center for The Arts, Fairfield
December 3rd: 8pm
December 4th: 2pm

 

A Winter Ballet – Nutcracker
Trumbull High School, Trumbull
December 4th: Shows at 1pm and 4pm

 

Echoes of Sinatra
Pavilions at Penfield Beach, Fairfield
December 4th: 7pm

 

CT Dance School Presents, The Nutcracker
Quick Center for The Arts, Fairfield
December 12th: Shows at 1pm and 4pm

 

Tom Petty Project Holiday Party
The Warehouse FTC, Fairfield
December 18th: 8pm

 

 

 

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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