(Somewhat fewer than)101 Ideas for Holiday Family Fun around Fairfield County - 2020 | Kids Out and About Fairfield County, CT

(Somewhat fewer than)101 Ideas for Holiday Family Fun around Fairfield County - 2020

KidsOutAndAbout is Fairfield County's online guide to everything for kids, teens, and families! Typically we list (MORE than) 101 ideas for holiday family fun, but. . . it's 2020, which means a bit less is happening than usual. 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 2020!

Santa Sightings

Nov. 27, 28, 29; Dec. 5, 6, 12, 13, 19, 20, 2020 Santa’s Trolley Winter Wonderland at Shore Line Trolley Museum
Nov 27-Dec 22, 2020 (closed Sundays) 12th Annual Greenwich Reindeer Festival - Sam Bridge Nursery & Greenhouses
Dec 1, 2020 The Town of Stratford’s Annual Holiday Lighting Festival
December 4-5, 2020-**CANCELED*** Bethlehem Christmas Festival


Old-Time Christmas

December 12, 2020 **SOLD OUT** Winter Wonderland- New Canaan Nature Center


Light Displays

Daily from Nov 13, 2020 - Jan 2, 2021 (closed 12/31) Magic of Lights
November 20, 2020 - January 10, 2021 (Select dates) Holiday Lights at the Bronx Zoo
November 21, 2020 (Virtual Event) A Diwali Virtual Celebration - Danbury Library
Nov 25 -Jan 3, 2021 Festival of Silver Lights- Meriden, CT
Weekends November 27 - December 29, 2020 Winterfest and Tunnel of Lights
December 11, 2020 Festival of Lights at Olde Mistick Village


Living Nativities

Dec 12, 2020- Virtual RCA Nativity Pageant- Virtual


Holiday Theatre

Multiple Dates starting Dec 4, 2020 A Center Stage Christmas @ Center Stage Theatre
Dec 6, 2020 Dance To The Holidays - The Ridgefield Playhouse
Dec 12, 2020 (Virtual Event) Something Beautiful from Iceland ~ Holiday Concert with Ragga Grondal, Svavar Knutur, and Kristjana Stefans
Dec 13, 2020 (Virtual Event) Hip Hop Nutcracker - The Bushnell
Dec 19, 2020 (Virtual Event) Moscow Ballet's Great Russian Nutcracker Live Stream
Dec 19, 2020 (Virtual Event) Christmas Around the World with Puppeteer Robin McCahill
Dec 19, 2020 A Slightly Wicked Holiday Show - The Ridgefield Playhouse


Holiday Concerts

Nov 19- Dec 24, 2020 (Virtual Event) Once Upon a Virtual Holiday - Stamford Town Center
Dec 12, 2020 (Virtual Event) Jim Brickman Comfort and Joy at Home (Virtual Event) - Fundraiser for the Bushnell Center
Dec 13, 2020 (Virtual Event)

Jim Brickman Comfort and Joy at Home- Palace Theatre Fundraiser


Christmas Tree Experience

  CT Audubon Society - H. Smith Richardson Tree Farm- Westport
  Averill Farm- Washington
  Belinsky Farm- Oxford
  Bob's Tree Farm- Bethel
  Fairview Tree Farm- Shelton
  Horse Listeners Orchard- Ashford
Opens Nov 21, 2020 Jones Family Farm- Shelton
Opens Nov 27, 2020  Maple Hollow Tree Farm- New Hartford


Ice Skating

Opening Nov 27, 2020 (weather permitting) WPAL Rink @ Longshore
  Winter Garden Ice Arena
  Wonderland of Ice
Reservations Required in 2020 Darien Ice House


Dec 10-18, 2020 CHANUKAH-At Chabad of Fairfield
Multiple Dates starting Dec 12, 2020 Chanukah at Chabad - Chabad of Stamford
Dec 13, 2020 Giant Menorah Lighting- Latham Park
Dec 14, 2020 Menorah Lighting- Stratford CT


Shopping & Craft Fairs

Nov 7, 2020 Holiday Market at Greenburgh Nature Center
Multiple Weekend Dates starting Nov 14, 2020 Flanders Artisan Marketplace
Nov 13-22, 2020- **Extended weekends Dec 5-20, 2020 Holiday Boutique In The Barn
Nov 20-22, 2020 The SoNo Collection - 2020 Wright-Way Productions Christmas Market
Dec 1 - 24, 2020 (Virtual Event) Virtual Greenwich Holiday Stroll, 24 Days of Holiday Shopping & Dining Dec 1-24


New Year's Eve

Dec 31, 2020 (Virtual Event) LIVE Virtual Noon Year's Eve Storytime with Danbury Library
Dec 31, 2020  New Year’s Eve Celebration at Windham Mountain



Nov 24, 2020-Feb 14, 2021 27th Annual Holiday Train Show at the CT River Museum
Nov 28 - Jan 6, 2021 Winter Wonderland Walk at Beardsley Zoo
Dec 4, 2020 Outdoor Adventures: Family Night Hike at SM&NC
December 6-12, 2020  Holiday Festival- Newtown, CT (virtual and in Person activities)
Dec 12, 2020 Boathouse Kids Crafts – December Holiday Luminaries at Connecticut River Museum
Dec 19, 2020 (Virtual Event) The Science and Indigenous Folklore of Santa and His Reindeer with Moki Kokoris

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!