101 Ideas for Holiday Family Fun around Fairfield County - 2021 | Kids Out and About Fairfield County, CT

101 Ideas for Holiday Family Fun around Fairfield County - 2021

KidsOutAndAbout is Fairfield County's online guide to everything for kids, teens, and families!  The activities we've listed here are confirmed for this year, but many require reserving ahead of time, and please keep in mind that events could be canceled... so click through to make arrangements. Enjoy the holidays!

If we're missing an activity that should be on our list, please email Mindy Mangan at mindy@kidsoutandabout.com. Please make sure to include a link to the event when you email. Thank you!

If you don't already receive our free weekly e-newsletter for Fairfield County, sign up today to make sure you're in the know about free stuff, festivals, classes, camps, vacation ideas, and all the best events near you! In the meantime, enjoy the ideas below for holiday family fun in 2021!

Santa Sightings

Multiple Days Starting Nov 19, 2021 Photos with Santa - Stamford Town Center
Multiple Days starting Nov 26, 2021 Santa Express - Naugatuck Railroad
Multiple Days starting Nov 26, 2021 Santa Photos at Ridge Hill
Multiple Days starting Nov. 26, 2021 Santa’s Trolley Winter Wonderland at Shore Line Trolley Museum
Multiple Days Nov. 26 - Dec 20, 2021 Selfies with Santa - The SoNo Collection
Nov 26-Dec 24, 2021 (closed Sundays) 13th Annual Greenwich Reindeer Festival - Sam Bridge Nursery & Greenhouses
Multiple Days Starting Nov 27, 2021 Pictures with Santa at Rocking Horse Ranch Resort
Dec 3, 4, 9-12, 2021 Santa's Walking Wonderland - Indian Rock
December 3-4, 2021 Bethlehem Christmas Festival
Dec 4, 2021 Santa at Auerfarm
Dec 4-5, 2021 The 21st Annual Hay Ride With Santa At Cove Island
Dec 5, 2021 RCA Santa Run- 2021
Dec 5, 2021 Pet Photos with Santa- Stamford Town Center Mall
Dec 5, 2021 Heights and Lights - Stamford Downtown 
Dec 7, 2021 The Town of Stratford’s Annual Tree Lighting
Dec 12 and 19, 2021 Santa Brunch - Powder Ridge

 

Old-Time Christmas

Nov 27, 28, 2021 Holiday Wreath Making - Bellamy-Ferriday House & Garden
Multiple Dates Starting Dec 1, 2021 The Webb-Deane-Stevens Museum’s History of Christmas Tour
Dec 2, 2021 Holidays on Main at Webb-Deane-Stevens Museum Store
Multiple Dates Starting Dec 8, 2021 "Holiday Enchantment at the Mansion" Tour at The Lockwood-Mathews Mansion Museum
Dec 11, 2021 Winter Wonderland- New Canaan Nature Center
Dec 18, 2021 Candy House Workshop at Fairfield Museum

 

Light Displays

Daily from Nov 19, 2021 - Jan 2, 2022 Magic of Lights - East Hartford
Nov 19, 2021 - Jan 9, 2022 (Select dates) Holiday Lights - The Bronx Zoo
Nov 19, 2021 - Jan 31, 2022 Holiday Lights Spectacular - Olde Mistick Village
Multiple Dates Starting Nov 24, 2021 American Museum of Natural History Presents: Origami Holiday Tree
Nov 24 - Jan 1, 2021 Festival of Silver Lights- Meriden, CT
Multiple Dates starting Nov 25, 2021 Illuminate the Farm at Queens County Farm Museum
Multiple Dates starting Nov 26, 2021 The SoNo Collection - Holiday Bells Grove™
Weekends Nov 26 - Dec 30, 2021 Winterfest and Tunnel of Lights
Nov 27 - Jan 2022 Worldwide Lights Celebration at Stepping Stones
Nov 28, 2021 RCA Lights Up Rowayton and Egg Nog Contest
Dec 10, 2021 Festival of Lights - Olde Mistick Village

 

Living Nativities

Dec 11, 2021 RCA Nativity Pageant- Virtual

 

Holiday Theatre

Nov 27, 2021 Elf on A Shelf (Touring)- Oakdale Theatre
Nov 28, 2021 SENSORY FRIENDLY: Rudolph The Red-Nosed Reindeer - Bushnell Center
Nov 28, 2021 Rudolph The Red-Nosed Reindeer - Bushnell Center
Multiple Dates starting Dec 3, 2021 Irving Berlin's White Christmas - Center Stage Theatre
Dec 4 and 5, 2021 A Christmas Carol - Powerhouse Theatre in Waveny Park
Dec 11, 2021 The Kids Komedian - Stepping Stones
Dec 10, 11, 2021 Cirque Dreams Holidaze (Touring) - Oakdale Theatre
Dec 10, 11, 12, 2021 The Nutcracker - Ridgefield Playhouse
Dec 11, 2021 Holiday Cirque Spectacular with the Hartford Symphony Orchestra
Dec 11, 12, 2021 All Together Now! - NPT Holiday Show - Fairfield Theatre Company
Dec 11, 12, 2021 Ballet Theatre's Nutcracker at The Bushnell Center
Dec 16, 2021 Christmas With The Celts - Ridgefield Playhouse
Dec 17, 2021 Hip Hop Nutcracker - The Bushnell
Dec 19, 2021 Dance To The Holidays With Keo Motsepe & Anna Trebunskaya - Ridgefield Playhouse
Dec 19, 2021 O. Henry’s The Gift of the Magi at Queens County Farm Museum
Dec 26, 2021 Shen Yun- The Bushnell
Dec 26 and Dec 29, 2021 Jack Frost - Stepping Stones

 

Holiday Concerts

Sat and Sun Nov 27 - Dec 19, 2021 Holidays in Harmony - Stamford Town Center
Nov 27 and Dec 18, 2021 Industrial Rhythm “Litt Percussion Show” - Stepping Stones
Dec 3, 4, 5, 2021 Hartford Symphony Orchestra's Tchaikovsk & Grieg - The Bushnell
Dec 6, 2021 Broadway Unplugged - Holiday Edition - Starring Bryan Perri and Heidi Blickenstaff
Dec 18, 2021 A Virtual Laurie Berkner Family Concert
Dec 18, 19, 2021 Stamford Symphony Holiday Performance at Stamford Town Center
Dec 19, 2021 Jim Brickman The Gift of Christmas LIVE! - Bushnell Center

 

Christmas Tree Experience

  Averill Farm- Washington
  Belinsky Farm- Oxford
  Bob's Tree Farm- Bethel
  CT Christmas Tree Growers Assoc
  Fairview Tree Farm- Shelton
  H. Smith Richardson Tree Farm- Westport
  Horse Listeners Orchard- Ashford
Opens Nov 20, 2021 (reservations needed) Jones Family Farm- Shelton
Opens Nov 26, 2021 Maple Hollow Tree Farm- New Hartford

 

Ice Skating

Opening Nov 26, 2021 (weather permitting) WPAL Rink @ Longshore
  Winter Garden Ice Arena
  Wonderland of Ice
  Darien Ice House

Active Holidays

Nov 27, 2021 Thanksgiving Weekend Waddle - New Canaan Nature Center
Dec 4, 2021 Santa Made Me Do It 5K - Bethlehem, CT

 

 Chanukah

Nov 28, 2021 Giant Menorah Lighting- Latham Park
Nov 28 - Dec 6, 2021 CHANUKAH-At Chabad of Fairfield
Dec 2, 2021 Menorah Lighting- Stratford CT
Dec 4, 2021 Menorah Parade- Chabad to Latham Park
Dec 5, 2021 Menorah Lighting- The SoNo Collection

 

Shopping & Craft Fairs

Nov 6 - Dec 19, 2021 (Saturdays and Sundays) Art on Market - Ridge Hill
Nov 13, 2021 2021 Continuum Holiday Bazaar - New Haven, CT
Multiple Weekend Dates starting Nov 13, 2021 Flanders Artisan Marketplace
Nov 13-14, 2021 Holiday Market - Greenburgh Nature Center
Nov 13-14, 2021 Early Bird Holiday Trunk Show - Silvermine Arts Center
Nov 14, 2021 A Very Gifty Christmas - Newtown, CT
Nov 19 - Dec 19, 2021- Select Days Holiday Boutique In The Barn
Nov 20, 2021 Holiday Market- New Canaan Nature Center
Nov 20-21, 2021 Pop Up Market - Fairfield Museum and History Center
Nov 21, 2021 Clay Art Center Clay Holiday Market Opening Event
Multiple Days starting Nov 26, 2021 Wreath Display & Silent Auction - NBMAA
Dec 2, 2021 Holiday Market - Stamford Museum and Nature Center
Dec 3, 2021 Holiday Express Train Show Opening Night at Fairfield Museum
Dec 5, 2021 Holiday Celebration & Maker's Market - NBMAA
Dec 11, 2021 Lachat's Winter Market
Dec 11-12, 2021 Silvermine Seasonal Sale & Fundraiser - Silvermine Arts Center
Dec 12 and 19, 2021 Mountainside Holiday Market at Powder Ridge

 

New Year's Eve

Dec 31, 2021 Cirque De Light – Stepping Stones
Dec 31, 2021  New Year’s Eve Celebration at Windham Mountain
Dec 31 - Jan 1, 2022 Ring in the New Year at Rocking Horse Ranch Resort
Dec 31, 2021 New Year's Eve Torchlight Parade at Ski Sundown

 

Miscellaneous

Various Dates starting Nov 13, 2021 Holiday Train Show - Greenburgh Nature Center
Nov 23, 2021-Feb 20, 2022 28th Annual Holiday Train Show - the CT River Museum
Nov 26, 2021- SOLD OUT *** SOLD OUT****Candy Cane Hunt- Lachat Town Farm
Nov 26, 2021 Black Friday Art Camp- Creatively Wild
Multiple Dates Starting Nov 26, 2021 Holiday Bricktacular! - LEGOLAND Discovery Center Westchester
Nov 27, 2021 Gingerbread Decorating Event -- Open Arts Alliance
Nov 28, 2021 Trees In The Rigging Boat Parade - CT River Museum
Dec 2, 2021 Ornament Decorating Party - Gallery 53, Meriden, CT
Dec 3, 2021 Holiday Express Train Show Opening Night at Fairfield Museum
Multiple Dates Starting Dec 4, 2021 Holiday Happenings at Beardsley Zoo
Dec 4, 2021 Holiday Card Printmaking Workshop at Fairfield Museum
Dec 4, 5 2021  Holiday Festival- Newtown, CT (virtual and in Person activities)
Dec 11, 2021 Build a Train Workshop at Fairfield Museum

Below are items that have been posted to our calendar. If you are affiliated with a business hosting a holiday event that should be on our calendar, we'd love to see it there...it's free to post! Click here for instructions about how to add your organization to our list and easily post your events to our calendar!

 


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