Holiday Events

Family Friendly Holiday Events in Fairfield County

The weeks between Thanksgiving and New Year’s Day truly are the most wonderful time of the year! Christmas has been my favorite holiday ever since I was little, and somehow it only gets more magical now that I have kids of my own. Watching their eyes light up with excitement and wonder brings me right back to some of the most memorable times of my life. What makes the holidays special is different for all of us. But experiencing the season together, as a family, will always be most important. Here are a few of our favorite holiday events in Fairfield County that are sure to build memories that will stay in your little ones’ minds – and hearts – forever. Don’t miss these family friendly holiday events in Fairfield County!

Family Friendly Holiday Events in Greenwich

Greenwich Reindeer Festival & Santa’s Village, Greenwich, CT

Santa and three of his favorite reindeer have returned to “the North Pole on North Street” (aka Sam Bridge Nursery & Greenhouses) for the 11th Annual Greenwich Reindeer Festival & Santa’s Village! Sam Bridge is always a special place to visit, but the magic around the holidays is something that shouldn’t be missed! From now through December 24th, this stunning holiday décor destination has been transformed into Santa’s Workshop. Here children, adults, and even pets (on leashes!) can have their photo taken with Santa. But as exciting as Santa is, perhaps the best attractions of all take place in his Village! Right outside his workshop doors, families have the opportunity to visit the (live!) reindeer and enjoy train and carousel rides. We bundled up and paid a visit to the reindeer on one of the coldest days of December last year. It could have been one of those family outings that ended disastrously, but the joy that filled the kids’ eyes warmed our hearts more than any added layer ever could!

family friendly Holiday Events
Photo Credit: Greenwich Reindeer Festival Facebook Page

Greenwich Historical Society Candlelight, Greenwich, CT

At first glance, this festive evening at the Greenwich Historical Society does not seem overly kid-friendly. But don’t be fooled! On Sunday, December 15th, visitors both young and old are invited to take a tour of the Bush-Holley House, which will be done up in holiday style. Tours last approximately 45 minutes and interpret Christmas traditions as they were celebrated by the Bush and Holley families centuries ago. If touring this colonial home isn’t your little one’s cup of hot chocolate, you can still have a wonderful time in the Vanderbilt Education Center listening to holiday music, enjoying treats, making crafts, and visiting with Santa Claus!

Holiday Events
Photo Credit:

Watch Santa Rappel in Stamford

Heights & Lights, Stamford, CT

Have you ever seen Santa Claus scale the side of a building? I assume your answer is “no”, so I’m here to change that! On Sunday, December 8th, Santa, Rudolph, and the Grinch will twist and fly as they make their way down from 22 stories high above downtown Stamford. The crowd of festive thrill-seekers is invited to cheer them on as they descend from Landmark Square (one of Stamford’s tallest buildings!). Like in years past, New York Yankees’ general manager, Brian Cashman, will join Santa and his crew as a guest rappeler. Once they’ve all made it safely back to solid ground, follow them to Latham Park to view the annual tree lighting and listen to carolers sing holiday music.

Santa Rappel in Stamford
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Family Friendly Holiday Events in New Canaan

New Canaan Nature Center Winter Wonderland, New Canaan, CT

My fingers are crossed that just the right amount of snow will fall for New Canaan Nature Center’s “Winter Wonderland” on Saturday, December 14th. Guests of this magical annual event will be transported into a whole new world filled with fun, holiday activities for the entire family to enjoy! Santa will welcome visitors throughout the day, a roaring campfire will be ready for roasting chestnuts and marshmallows, a giant model train will depict the town of New Canaan, and you can participate in a number of crafts and games (like a wacky Winterland scavenger hunt). Of course, you won’t want to leave before taking a horse-drawn wagon ride. And don’t forget to sign up for the family gingerbread house contest when you arrive– it’s first come, first serve!

New Canaan Nature Center
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To see my complete roundup of Holiday events, head to my website: Busy Little Bee.

About Lauren Haley

Lauren Haley was born and raised in Darien, CT. Lauren is the founder of Busy Little Bee. As a busy mom looking for activities for her girls, Lauren always found herself spending hours on various websites comparing schedules, costs, and class descriptions. And when it came time to start the daunting task of finding a preschool, it was impossible for her to locate a quick overview of each school’s approach to learning or identify open house and registration dates. Lauren quickly realized that navigating the logistics of activity registration and preschool enrollment didn’t need to be so difficult, so Busy Little Bee was born! Lauren lives in Darien, CT with her husband, Chris, and three children, Parker, Madison, and Hudson. Website:

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Suburbs 101 is an online lifestyle guide for the New York Suburbs of Westchester County, Long Island, Fairfield County and Northern New Jersey.  Get the inside scoop on what it’s really like to live in the New York suburbs through our weekly interviews with local suburbanites and features on Food, Fashion, Home, Travel, and Local Events. Be sure to Follow Us on InstagramLike Us on Facebook and subscribe to our Monthly Newsletter.

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