101 Ideas for Holiday Family Fun around Fairfield County - 2025
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 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 2025!
17th Annual Greenwich Reindeer Festival & Santa's Workshop
November 28 - December 24, 2025Santa and his three LIVE reindeer are returning to Greenwich for the 17th Annual Greenwich Reindeer Festival & Santa's Workshop presented by Jenny Allen & Kristen Studwell at Compass Real Estate, "The North Pole on North Street", Sam Bridge Nursery & Greenhouses, 437 North Street, Greenwich. The cherished town tradition continues for the seventeenth consecutive year at this expansive nursery where visitors can have their photo taken with Santa, meet the reindeer and also enjoy the beautiful Santa's Workshop, which provides more space for families while they wait in line for their photo with Santa. This all takes place just minutes from downtown Greenwich. Parking is free. We are proud to support Kids In Crisis for the 17th consecutive year. Every day November 28-December 24 except Sundays.
101 Ideas for Holiday Family Fun around Fairfield County - 2025
Santa Sightings
Old-Time Christmas
| Multiple dates starting Nov 22, 2025 | The Holiday Wish Express – Stamford Town Center |
| Multiple dates starting Nov 28, 2024 | Christmas by Candlelight 2025 - Old Sturbridge Village |
| Dec 5, 2025 | Holiday Stroll Open House — Keeler Tavern Museum |
| Multiple dates starting Dec 5, 2025 | 2025 Lantern Light Village | Mystic Seaport Museum |
| Dec 6, 2025 | Holiday Carnival at Olde Mistick Village |
| Dec 13, 2025 | Build-a-Train Family Workshop | Fairfield Museum and History Center |
Light Displays
Holiday Theatre
| Multiple dates starting Nov 6, 2025 | Christmas Spectacular Starring The Radio City Rockettes |
| Multiple date starting Nov 14, 2025 | Irving Berlin's White Christmas - The Goodspeed |
| Nov 29 & 30, 2025 | The Nutmeg Ballet's The Nutcracker at The Bushnell |
| Multiple dates Dec 4 - 28, 2025 | Twas the Night Before... by Cirque du Soleil - Theatre at Madison Square Garden |
| Nov 28 & 29, 2025 | Cirque Dreams: Holidaze / Toyota Oakdale Theatre |
| Multiple dates starting Nov 29, 2025 | Santa Story 3 - Downtown Cabaret |
| Multiple dates starting Dec 3, 2025 | Scrooge and Marley — LegacyTheatreCT |
| Multiple dates starting Dec 11, 2025 | A Christmas Carol Experience 202 - Fairfield Center Stage |
| Dec 13, 2025 | Woodbury Ballet presents The Nutcracker 2025 at The Bushnell |
| Dec 20 & 21, 2025 | Connecticut Ballet's 'The Nutcracker' at The Bushnell |
Holiday Concerts
| Dec 1, 2025 | DCINY Holiday - Carnegie Hall |
| Dec 10, 2025 | Béla Fleck & the Flecktones - The Beacon Theatre |
| Dec 12, 13 & 14, 2025 | HSO Masterworks Series: Winter Dreams at The Bushnell |
| Dec 13, 14, 2025 | Sounds of the Season - New York Philharmonic |
| Dec 17, 2025 | Travelers Chorale Concert – The Colors of the Season | The Bushnell |
| Dec 17-20, 2025 | Home Alone In Concert - New York Philharmonic |
| Dec 28, 2025 | Concert of the Future: "A Christmas Dream" - Carnegie Hall |
Chanukah Events
| Dec 14, 2025 - Jan 2, 2025 | Chanukah - Chase Family Gallery - Mandell JCC |
| Dec 14, 2025 | Lighting of the Menorah- Parade Plaza – Downtown New London Association |
Kwanzaa Events
| Dec 26, 2025 | Kwanzaa Lighting Celebration – Downtown New London Association |
Christmas Tree Experience
| Multiple dates starting Nov 23, 2025 | Christmas Trees – Maple Row Farm |
| Multiple dates starting late Nov, 2025 | SABIA TREE FARM - Home |
| Opening Nov 28, 2025 | Pell Family Farm |
| Multiple dates starting Nov 29, 2025 | Christmas Home - Fairview Tree Farm |
Active Holidays
| Nov 27, 2025 | Shoreline Turkey Trot 5K - West Haven, CT |
| Dec 6, 2025 | Santa Made Me Do It |
| Dec 7, 2025 | CLA Blue Back Mitten Run | HMF Events |
Ice Skating
| All year | Wonderland Of Ice |
| All Year | Winter Garden Ice Arena |
| All Year | Darien Ice House Public Skating |
| Open weekends | Milford Ice Pavilion - Public Skate |
| Dates starting in Nov, 2025 | Sono Ice House |
Shopping & Craft Fairs
| Multiple dates starting Nov 20, 2025 | Holiday Boutique in the Barn: Keeler Tavern Museum |
| Nov 22, 2025 | Holiday Market | New Canaan Nature Center |
| Nov 21 & 22, 2025 | Holly Berry Festival – Holly Berry Festival |
| Nov 22 & 23, 2025 | Access for All Community Day | Holiday Makers Market | New Britain Museum of American Art |
| Nov 23, 2025 | Holiday Craft Fair – Roaring Brook Nature Center Roaring Brook |
| Nov 23, 2025 | Frosty's Christmas Festival | Middlebury CT |
| Multiple dates starting Nov 29, 2025 | Annual Holiday Market: Featuring Indigenous and Local Artisans | The Institute for American Indian Studies Museum & Research Center |
| Dec 13, 2025 | Santa Shopping Stroll – Downtown New London Association |
| Dec 13, 2025 | Handmade Holiday Bazaar at Connecticut Science Center |
New Year's Eve
| Dec 31, 2025 | Kids Countdown to New Year with Steve Elci & Friends | Mystic Seaport Museum |
Miscellaneous
Below are upcoming holiday events that have been posted to our calendar by local organizations. 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!
Christmas Tree Farms
Fairfield County offers a delightful selection of Christmas tree farms that bring the magic of the holiday season to life. Families can enjoy the cherished tradition of selecting the perfect tree while exploring picturesque landscapes and engaging in festive activities. From charming local farms to larger operations, each location provides a unique experience, complete with hayrides, hot cocoa, and seasonal treats. Many farms also host holiday events, making it easy to create lasting memories with loved ones. Whether you’re looking for a classic fir or a unique spruce, the Christmas tree farms around Fairfield promise to make your holiday celebrations truly special.
Subscriptions Boxes: Gifts That Keep on Giving
Send thoughtful choices to the ones you love near and far, and plan some excellent expected surprises for your own family in the months to come. KidsOutAndAbout has put together of some of our favorite choices with a range for all different ages and interests.
