101 Ideas for Holiday Family Fun around Fairfield County - 2023 | Kids Out and About Fairfield County, CT <

101 Ideas for Holiday Family Fun around Fairfield County - 2023

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 2023!

Santa Sightings

Multiple Days Starting Nov 9, 2023 Photos with Santa - Stamford Town Center
Multiple Days starting Nov 20, 2023 Santa Photos at Ridge Hill
Multiple Dates starting Nov 24, 2023 Santa Express — Railroad Museum of New England - Naugatuck Railroad
Multiple Days starting Nov. 24, 2023 Visit Santa at Shore Line Trolley Museum
Nov 24-Dec 23, 2023 (closed Sundays) 15th Annual Greenwich Reindeer Festival - Sam Bridge Nursery & Greenhouses
Nov 30, 2023 Holiday Lighting Festival - Town of Stratford
December 1, 2, 2023 Christmas Festival - Bethlehem, CT
Dec 2, 2023 Santa at Auerfarm
Dec 2 and Dec 9, 2023 The 23rd Annual Hay Ride With Santa - Cove Island
Dec 3, 2023 The Mike Barbis Santa Toy Drive - Rowayton
Dec 3, 2023 Heights and Lights - Stamford Downtown
Dec 9-10, 16-17, 23, 2023 Breakfast with Frosty - Connecticut's Beardsley Zoo

 

Old-Time Christmas

Multiple dates starting Nov 24, 2023 Christmas by Candlelight 2022 - Old Sturbridge Village
Multiple Dates starting Dec 1, 2023 Holiday at The Homestead - Boothe Memorial Park and Museum
Dec 1, 2023 Holiday Stroll Open House - Keeler Tavern Museum
Dec 2, 2023 Holiday Carnival at Olde Mistick Village
Dec 3, 2023 Christmas in Clinton OPEN HOUSE
Multiple Dates Starting Dec 7, 2023 The Webb-Deane-Stevens Museum’s History of Christmas Tour
Dec 8, 2023 Holiday Caroling Party - Pequot Library
Dec 16, 2023 - **SOLD OUT Winter Wonderland- New Canaan Nature Center - SOLD OUT

 

Light Displays

Multiple Dates Begining Nov 17 - Dec 24, 2023 The Holiday Wish Express - Stamford Town Center
Multiple Dates Begining Nov 17 - Dec 31, 2023 Festival of Lights at Harvest Moon
Multiple Days Starting Nov 18 - Dec 23, 2023 Glow Hartford | Holiday Indoor Light Festival
Multiple Days Starting Nov 24 - Dec 24, 2023 The All New Holiday Stroll- Stamford’s Mill River Park
Select Nights Nov 25 - Dec 23, 2023 Night of Lights Merry Christmas Hayride! at Fairview Tree Farm
Nov 30, 2023 Holiday Tree Lighting - Stratford, CT
Nov 30, 2023 Christmas Lighting Celebration - Stew Leonard's Norwalk
Multiple Dates beginning Nov 11, 2022 - Jan 8, 2023 Illuminate the Farm at Queens County Farm Museum
Multiple Days Starting Nov 20, 2023 Worldwide Lights Celebration at Stepping Stones
Daily from Nov 23 - Dec 31, 2023 Magic of Lights - East Hartford
Nov 17, 2023 - Jan 7, 2024 (Select dates)

Holiday Lights - The Bronx Zoo

Multiple Dates Starting Nov 24, 2023 Holiday Lights - Lake Compounce
Nov 19, 2023 The Lighting of Ridge Hill
Multiple Days Starting Nov 21, 2023 Origami Holiday Tree - American Museum of Natural History
Multiple Days starting Nov 24, 2023 Home For The Holidays - Mystic Aquarium
Multiple Days Nov 24 - Dec 30, 2023 Winterfest and Tunnel of Lights - Connecticut Trolley Museum
Nov 26, 2023 RCA Lights Up Rowayton and Egg Nog Contest
Nov 30, 2023 Holiday Lighting Festival - Town of Stratford
Dec 8, 9, 15, 16, 21, 22, 23, 2023 2023 Lantern Light Village - At Mystic Seaport Museum
Dec 8, 2023 Festival of Lights - Olde Mistick Village
Dec 10, 2023 Holiday Buoy Tree Lighting - Milford

 

Living Nativities

Dec 9, 2023 RCA Nativity Pageant- Pinkney Park

 

Holiday Theatre

Nov. 24, Dec 2, and Dec 16, 2023 The Nutcracker by the New Paltz Ballet at Rocking Horse Ranch Resort
Nov 28, 2023 A Magical Cirque Christmas - Palace Theater
Nov 29, 2023 The Clairvoyants - Holiday Spectacular - Ridgefield Playhouse
Multiple Dates Starting Nov 29, 2023 A Christmas Carol at The Legacy Theatre
Nov 30, 2023 Nutcracker! Magical Christmas Ballet - Toyota Oakdale Theatre
Multiple Days Dec 1 - Dec 17, 2023 A Christmas Story - Powerhouse Theatre in Waveny Park
Dec 1-3, 2023 Ballet Theatre's Nutcracker at The Bushnell Center
Dec 3, 2023 SENSORY FRIENDLY- Ballet Theatre's Nutcracker at The Bushnell Center
Dec 3, 2023 Woodbury Ballet Presents The Nutcracker - Palace Theater - Waterbury

Dec 8, 9, 2023

Cirque Dreams Holidaze at Oakdale Theatre
Dec 8, 9, 10, 2023 The Nutcracker - Ridgefield Playhouse
Dec 8, 9, 2023 Elf The Musical Jr! at Edmond Town Hall
Dec 10, 2023 Peppa Pig: Sing-Along Party - Palace Theater - Waterbury
Dec 13, 2023 A Christmas Story – 40TH Anniversary Movie - Ridgefield Playhouse
Dec 16, 2023 HSO POPS! SERIES: Holiday Cirque! - The Bushnell
Dec 16, 2023 O. Henry’s The Gift of the Magi at Queens County Farm Museum
Dec 16, 17, 2023 Connecticut Ballet presents 'The Nutcracker' at The Palace
Dec 17, 2023 Holiday Open House - Sensory-Friendly/Relaxed - The Bushnell
Dec 22, 23, 2023 Connecticut Ballet presents 'The Nutcracker' at The Bushnell
Dec 30, 2023 The Hip Hop Nutcracker - Palace Theater - Waterbury

 

Holiday Concerts

Nov 18, 2023 Laurie Berkner - Holiday Concert - College Street Music Hall
Dec 2, 2023 "Home Alone" in Concert with the Waterbury Symphony Orchestra at Palace Theater- Waterbury
Dec 9, 2023 Mannheim Steamroller Christmas at Palace Theater - Waterbury
Dec 9, 10, 2023 The Holiday Show - The New Paradigm Theatre Co - Fairfield Theatre Company
Dec 17, 2023 Ridgefield Chorale Presents: Holiday Pops Concertat Ridgefield Playhouse
Dec 20, 2023 Travelers Chorale: 2023 Holiday Show - The Bushnell
Dec 20, 2023 *** SOLD OUT ***Christmas With The Celts at Ridgefield Playhouse

 

Holiday Trains

Weekends starting Nov 18 - Dec 10, 2023 Holiday Train Show - Greenburgh Nature Center
Nov 21, 2023 - Feb 18, 2024 30th Annual Holiday Train Show - the CT River Museum
Dec 2, 2023 Holiday Express Train Show Opening Night at Fairfield Museum

 

Christmas Tree Experience

  Averill Farm- Washington
  Belinsky Farm- Oxford
  Bob's Tree Farm- Bethel
  CT Christmas Tree Growers Assoc
  Fairview Tree Farm- Shelton
  Jones Family Farm- Shelton
  Plasko's Farm

 

Ice Skating

  WPAL Rink @ Longshore
  Winter Garden Ice Arena
  Wonderland of Ice
  Darien Ice House

Active Holidays

Nov 24, 2023 Black Friday Hike - Flanders Nature Center
Nov 25, 2023 Thanksgiving Weekend Waddle - New Canaan Nature Center
Dec 2, 2023 Santa Made Me Do It 5K - Bethlehem, CT

 

 Chanukah

Dec 7, 2023 Menorah Lighting Celebration - Stew Leonard's Norwalk
Dec 7, 2023 Menorah Lighting - Ridge Hill
Dec 9, 2023 Chanukah Menorah Car Parade - Stamford Chabad
Dec 10, 2023 Chanukah Concert - Micha Biton - JCC of Greater New Haven
Dec 10, 2023 Giant Menorah Lighting- Latham Park
Dec 10, 2023 Hanukkah Party For All (Ages 10+) - Park City Music Hall
Dec 10, 2023 Chanukah Menorah Lighting - Unite Through Light! - Chabad of Fairfield
Dec 12, 2023 Menorah Lighting- Stratford CT

 

Shopping & Craft Fairs

Multiple Dates starting Nov 11, 2023 Flanders Artisan Marketplace
Nov 12, 2023 A Very Gifty Christmas - Newtown, CT
Nov 16 - Dec 17, 2023- (Thurs - Sun) Holiday Boutique In The Barn - Keeler Tavern Museum
Multiple Days Nov 16 - Dec 23, 2023 Clay Holiday Market - Clay Art Center
Nov 18, 2023 Holiday Market- New Canaan Nature Center
Nov 18, 2023 Indigenous Craft Fair - Mystic Seaport Museum
Nov 18-19, 2023 Holiday Market at Greenburgh Nature Center
Nov 18-19, 2023 Holiday Pop-Up Market- Fairfield Museum and History Center
Multiple Days starting Nov 25, 2023 Annual Holiday Market - The Institute for American Indian Studies
Multiple Days starting Dec 2, 2022 Wreath Display & Silent Auction - NBMAA
Dec 2, 2023 2023 Continuum Holiday Bazaar - New Haven, CT
Dec 2, 2023 Holiday Stroll - Westport Downtown
Dec 2, 2023 Lachat's Winter Market
Dec 3, 2023 Craft and Gift Fair at JCC of Greater New Haven
Dec 3, 2023 Holiday Celebration & Maker's Market - NBMAA
Nov 5, 2023 Farm & Artisan Market - Stamford Museum and Nature Center

 

New Year's Eve

Dec 31 - Jan 1, 2024 Ring in the New Year at Rocking Horse Ranch Resort
Dec 31, 2023 Noon Year's Eve - Newtown Community Center
Dec 31, 2023 Noon Year's Eve - EverWonder Children's Museum
Dec 31, 2023 Kids countdown to New Years with the BenAnna Band - At Mystic Seaport!

 

Miscellaneous

Nov 10, 2023 Fall Wreath Family Workshop - Fairfield Museum
Nov 12, 2023 Annual Thanksgiving Dinner - Webb Deane Stevens Museum
Nov 30, Dec 1, 21, 28, 2023 Baking Workshop for Kids at Edmond Town Hall (Ages 8-12)
Nov 18, 2023 Giant Balloon Inflation Party - Downtown Stamford
Nov 19, 2023 Stamford Downtown Parade Spectacular
Nov 26, 2023 Trees In The Rigging Boat Parade - CT River Museum
Dec 1, 2023 Henry Whitfield State Museum, Guilford - Firelight Festival
Dec 3, 2023 Homestead Holiday Workshop - Lachat Town Farm
Multiple Dates Starting Dec 3, 2023 Holiday Festival- Newtown, CT (virtual and in Person activities)
Dec 9, 16, 2023 Flashlight Candy Cane Hunt- Lachat Town Farm
Dec 9, 10, 2023 Family Day! Wreath Festival Fundraiser 2023 - Woodcock Nature Center
Dec 26, 27, 28, 2023 Drop-in: Paint-a-Train - 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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