Winter Activities for the Holiday Season - FairfieldMoms


December is one busy month!  Whether you’re prepping for a Holiday party, shopping for your family & friends, planning a get-a-way over the break, FairfieldMoms has you covered when it comes to local events!  There are SO many activities, holiday fairs, photos with Santa, concerts & performances happening around Fairfield that we thought it would be helpful to map them all out for you!  You can also always check out our Calendar for details and updates!


Breakfast with Santa

Connect Beardsley Zoo
December 15th and 16th: 8:30am – 10:30am
December 22nd and 23rd: 8:30am – 10:00am
Get in the holiday spirit and join Frosty, Santa, and all their friends for Breakfast at the Zoo! 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.


Hub & Spoke
December 11th: 4:30pm – 7:30pm
Storytime with Santa, early dinner and fireside desserts


The Klein
December 1st: 9am – 11am
Have breakfast with Santa & friends! Saturday, December 1st from 9AM-11AM. Limited space is available, so don’t wait to reserve. Ticket sales for breakfast end 48 hours before event. Tickets: $5 per person


Mitchells of Westport
December 2nd: 9am – 11am
Join us for breakfast with Santa & Mrs. Claus!


The Pilot House
December 16th: 10am – 1pm
Enjoy a pancake breakfast and get your photo taken with our sensory sensitive Santa! This event will be a treasured memory for your family in our winter wonderland!


Tree Lighting

Fairfield Christmas Tree Lighting
November 30th: 6:15pm
Town Hall Green
The festivities begin at 6:15 pm with the Fairfield Woods, Roger Ludlowe and Tomlinson Middle School Chamber Choirs singing songs of the season and Fairfield Center Stage will wow you at 6:40 with an amazing performance. Enjoy some hot chocolate and free glow necklaces compliments of the Town Youth Council. First Selectman, Mike Tetreau will do the countdown to light the tree at 7:00 pm and Santa Claus arrives by Fire Engine soon after!


Norwalk Annual Tree Lighting
November 30th: 6pm
City Hall, 125 East Ave
Join us for the annual tree lighting celebration outside of City Hall. There will be entertainment, snacks, refreshments, crafts and a special visit from Santa!


Trumbull Holiday Tree Lighting
November 30th: 6pm
Trumbull Town Hall Gazebo
Santa will be arriving on the decorated fire truck! Performance by the Trumbull Youth Association, music by Madison Middle School Band, hot chocolate donated by Maefair Health Care Center and munchkins donated by Dunkin Donuts


Westport Annual Tree Lighting
December 5th: 5pm
Town Hall
The Staples High School Orphenians will perform a selection of seasonal songs as part of the proceedings. The Police Department Toy Drive Collection box will also be available to collect new, unopened and unwrapped toys for distribution to local families.


Fairfield University’s Annual Tree Lighting
December 6th: 6:15pm
Fairfield University
Join us, Lucas the Stag, Santa & Mrs. Claus as we light the tree, sing songs of the season, and share hot chocolate and cookies to warm your family’s spirits.


Wakeman Town Farm Holiday Tree Lighting
December 7th: 4:30pm
Wakeman Town Farm
Westport’s Wakeman Town Farm’s Tree Lighting has local soul. This year, Broadway actress Susan Terry will sing a few Holiday tunes and lead a festive sing-a-long. Volunteers pour hot cocoa and serve cookies. Free and open to the public!



Menorah Lighting

Chanukah Village & Menorah Lighting
December 2nd: 2pm.  Menorah Lighting at 4pm
Hosted by Chabad of Fairfield | Downtown on Post Road

Menorah Lighting Celebration
December 3rd: 5pm
Stew Leonard’s, Norwalk

Menorah Lighting in Downtown Westport
December 3rd: 6:15pm
Post Road & Main Street, Westport



Photos with Santa

Bass Pro Shop, Bridgeport
Weekdays: 10am – 8pm
Saturdays: 10am – 8pm
Sundays: 10am – 5pm
1 Bass Pro Drive, Bridgeport


Stew Leonard’s
Weekdays: 3pm – 6pm
Weekends: 10am – 6pm
100 Westport Ave, Norwalk


Mitchells, Westport
Every Saturday (12/1 – 12/22)
11am – 1pm
670 Post Road East, Westport


JWC’s A Visit to Santa’s House at Burr Mansion
December 8th: 10am – 4pm
December 9th: 10am – 2pm
739 Old Post Road, Fairfield
Purchase tickets prior or at the door


Jingle Bells Rock Family Day at Westport Historical Society
December 15h: 10am – 4pm
25 Avery Place, Westport


Winter Wonderland at New Canaan Nature Center
December 15th: 11am – 2pm
144 Oenoke Ridge, New Canaan


Santa Visits Jones Farms
December 15th: 10am – 4pm
December 16th: 10am – 4pm
606 Walnut Tree Hill Road, Shelton



Festivals & Fairs

Fairfield Christmas Tree Festival
November 30th: 10am – 7pm
December 1st: 10am – 5pm
December 2nd: 10am – 4pm
Burr Homestead, Fairfield

Holiday Express Train Show
November 30th: 5pm – 8pm (Opening Night)
December 1st – 31st – see website for all hours
Fairfield Museum and History Center

17th Annual Lamplight Stroll, Milford
November 30th: 5pm
Downtown Milford

Three Kings Bazaar
November 30th: 5:30pm – 8:30pm
December 1st: 10am – 3pm
First Church Congregational

Celtic Christmas Fair
December 1st: 9am – 3pm
Gaelic American Club

St. Nicholas Fair
December 1st: 10am – 4pm
St. Paul’s Episcopal Church

Scandinavian Club Annual Holiday Fair
December 1st: 10am – 3pm
Scandinavian Club

PopShop Holiday Market
December 1st: 10am – 3pm
The Warehouse @ FTC

33rd Annual Holiday Festival, Newtown
December 2nd: 11am – 4pm
Main Street, Newtown

Hub & Spoke’s Annual Sip & Shop
December 2nd: 5pm – 9pm
Hub & Spoke

Christmas in the Mansion
December 2nd: 12pm – 5pm
Laualton Hall, Milford

Mill Hill Elementary School Holiday Fair
December 4th: 6pm – 9pm
Mill Hill Elementary School, Southport

Holiday Shopping Bazaar
December 6th: 5pm – 9pm
Pious Bird, Bridgeport

Fairfield’s Downtown Holiday Shop & Stroll
December 6th: 6pm-9pm
Join FairfieldMoms at Happy Hour from 4-6pm at The Chelsea | End the night at 55 Wine Bar!

Let’s Wine about Winter Holiday Shopping Event
December 7th: 6pm – 9pm
Small to Tall Preschool, Bridgeport

1st Annual Stratfield Village Holiday House Tour
December 8th: 12pm – 6pm
Stratfield, Fairfield

Holiday Open House
December 8th: 11am – 4pm
Fairfield University Bookstore

Holiday Caroling Party & Open House
December 14th: 5pm – 7pm
Pequot Library, Southport

Jingle Bells Rock Family Day
December 15h: 10am – 4pm
Westport Historical Society

Winter Wonderland
December 15th: 11am – 2pm
New Canaan Nature Center



Performances & Concerts

The Elf Christmas Spectacular
December 1st: 12pm and 3pm
The Klein, 910 Fairfield Ave, Bridgeport
Tickets: $12 | Ages 2 and under FREE
The whimsical tale of an elf who goes to hilarious lengths to win a talent competition & a spot on Santa’s sleigh on Christmas Eve. Fun for all ages! Sing along with the cast and meet Santa after the show.


The Nutcracker “Sweet Tea” – Featuring The New England Ballet
December 2nd: 1pm
Burr Mansion, 739 Old Post Road, Fairfield
Tickets: $40 | Ages 3 and under FREE
Make Magical Holiday Memories! Enjoy Light fare, tea and sweets while taking in a magical vignette performance of the Nutcracker. Children may meet the dancers and have photos taken.


The Christmas Elf 2
December 7th: 4:30pm
Fairfield University Bookstore, 1499 Post Road, Fairfield
FREE and open to the public!  RSVP needed
In honor of the holidays the Christmas Elf 2 will participate in a special story time at Fairfield University Bookstore for ages 3 and up!


JWC Present’s “Santa’s House after Dark Nutcracker Night”
December 7th: 6pm
Burr Mansion, 739 Old Post Road, Fairfield
A special presentation of The Nutcracker from our Presenting Sponsor, Flash Pointe Dance. This event, for both children and adults, will include an extended 40-minute performance of the classic holiday ballet, along with an appearance by Mr. and Mrs. Claus to pass out cookies.


Fezziwig’s Party – A Christmas Carol Experience
December 8th: 11am and 1:30pm
December 9th: 11am and 1:30pm
Tickets: $10 | Ages 6 and up $8 (not recommended for kids under 6)
Fairfield Museum & History Center, 370 Beach Road, Fairfield
Enjoy a party with characters from Fairfield Center Stage’s “A Christmas Carol Experience.” Hear stories from Charles Dickens’ classic holiday tale, enjoy cookies & milk, craft a Victorian-inspired ornament and decorate a book to collect holiday messages from family and friends.


CT Dance School Annual Nutcracker
December 9th: 1pm and 4pm
Tickets $25-$45
The Regina A. Quick Center for the Arts at Fairfield University
1073 North Benson Road, Fairfield
Connecticut Dance School is proud to present our Holiday extravaganza of, The Nutcracker


A Christmas Carol Experience
December 14th and 21st: 6pm and 8pm
December 15h and 22nd: 12pm, 2pm, 6pm and 8pm
December 16th and 23rd: 12pm and 2pm
Burr Mansion, 739 Old Post Road, Fairfield
In this original adaptation of the beloved Charles Dickens classic, created as an immersive tour through Burr Mansion, the audience will follow Ebenezer Scrooge and the Ghosts of Christmas Past, Present and Future from room to room. Audiences will be guided from Scrooge & Marley’s to Bob Cratchit’s House to Mr. Fezziwig’s Christmas party (complete with figgy pudding and apple cider!) This one-hour-long version will be limited to 25 guests per show, and promises to be a unique, intimate, and unforgettable experience.


Norwalk Metropolitian Youth Ballet – The Nutcracker
December 14th (Nutcracker Suite – great for younger childred): 12pm
December 15th: 1pm and 6pm
The Regina A. Quick Center for the Arts at Fairfield University
1073 North Benson Road, Fairfield


The Carillon Holiday Concert
December 18th: 6:30pm and 8:30pm
Fairfield Warde High School, 755 Melville Ave


Candlelight Concert
December 20th: 6:30pm and 8:30pm
Roger Ludlowe High School, 785 Unquowa Road


Parent’s Night Out – Adults Only

Jingle & Mingle
November 29th: 6:30pm – 10pm
Burr Mansion, 739 Old Post Road, Fairfield
Be among the first to preview the Designer Decorated Holiday Showcase at the Burr Homestead. Featuring Beer & Wine from local breweries & vineyards and delightful delicacies by Vazzy’s. Live Entertainment by: Band Together!


Casino Noelle
December 1st: 6:30pm – 10:30pm
Burr Mansion, 739 Old Post Road, Fairfield
Premier Sponsor event. Enjoy an exciting evening of chance with our first ever casino night! Enjoy BlackJack, Poker, Craps, and Roulette! Full bar, delicious food by Vazzy’s and live & silent auctions! Celebrating out Festival Honoree Terry O’Connor, Master Auctioneer.
“Elves” level $125 pp- 200 chips
“Santas” level $200 pp- 300 chips
“Angels” leve $300 pp- 400 chips


Hub & Spoke’s Annual Sip & Shop
December 2nd: 5pm – 9pm
3001 Fairfield Ave, Bridgeport
Enjoy a glass of wine as you do some stress free shopping with local vendors


Santa’s House after Dark Trivia Night
December 6th: 7:30pm – 11pm
Burr Mansion, 739 Old Post Road, Fairfield
Adults only to enjoy the Burr Homestead dressed for the holidays and to test there knowledge of seasonal facts while sipping local brews and light refreshments. Be sure to wear your ugly sweater.


Pray for Snow at Two Roads Brewery Co.
December 8th: 12pm – 4pm
Two Roads Brewery, 1700 Stratford Ave, Stratford
Let’s summon the snow! REI’s Pray for Snow Party at Two Roads Brewing Company is back and better than ever. Break out your retro neon one-piece ski suit and grab your mono-board because it’s time to get RAD! Join us for music, drinks, retro-ski fashion show, and REI’s traditional Twinkie Roast. Tickets at



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

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