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Top 20 Things to Do in Winter in Fairfield County, CT

Top 20 Things to Do in Winter in Fairfield County, CT

Have the most fun this winter with our guide to the 20 must-do events in Fairfield County. Don't miss winter seasonal fun like ice skating at a local rink, visits with Santa and his reindeer, performances of The Nutcracker and Disney on Ice, and more!


1. Get in the holiday spirit at a Christmas tree festival.

A tradition for more than 30 years, the Fairfield Christmas Tree Festival at Burr Homestead in Fairfield is held in late November or early December. Attendees can shop for Christmas trees and wreaths, take a photo with Santa, and tour the designer-decorated rooms, all while contributing to a good cause—the festival donates proceeds to a worthy local organization each year.

2. Meet Santa's reindeer.


Meet those amazing animals who pull Santa’s sleigh at the Greenwich Reindeer Festival & Santa’s Workshop at McArdle’s Florist & Garden Center, open late November through late December. You can also get a photo with jolly Old St. Nick himself.

3. Cut your own Christmas tree.

Cut your own Christmas tree at Jones Family Farm in Shelton or another tree farm in the area.


4. Experience holiday lights in the park.

November ushers in the Fantasy of Lights at Lighthouse Point Park in New Haven, which runs through January. Bask in the glow of the mile-long route of holiday lights in many incarnations, including a gingerbread house and a holiday dragon. Some exhibits are animated, too!

5. See visions of sugar plums during a performance of The Nutcracker

the nutcracker

Westport’s Academy of Dance presents its annual production of The Nutcracker, a more than 30-year tradition, at Staples High School in Westport in early December. Find more area performances of the classic ballet.

6. Watch Santa scale a skyscraper.

Santa is used to climbing down the chimney, not down skyscrapers! But at Heights & Lights Rappelling Santa and Holiday Tree Lighting in early December, you can watch Santa descend 22 stories by rope from one of Stamford’s tallest buildings, Landmark Square. Once he reaches the ground, follow him up Bedford Street to Latham Park for an evening of holiday fun with live music and the annual lighting of Stamford’s holiday tree.

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7. Hit the slopes for skiing and snowboarding.

Grab your gear and pack up the kids for a day of skiing or snowboarding at one of the area’s family-friendly resorts, such as Mohawk Mountain Ski Area in Cornwall (Litchfield County).


8. Watch The Polar Express in IMAX.

polar express movie tom hanks

From late November through early January, you can catch The Polar Express in IMAX at the Maritime Aquarium in Norwalk. This perennial holiday film tells the tale of a young boy who doubts the existence of Santa Claus and gets taken on a magical Christmas Eve trip to the North Pole.

9. Check out a holiday train show.

Let your little ones delight in the magic of model trains at the annual Holiday Express Train Show at Fairfield Museum and History Center. From early December through early January, you can watch the trains wind around a winter wonderland of spectacular trees and beautiful holiday scenery. Find details on this and more train rides, exhibits, and displays in the area in our train guide.


10. Ring in the New Year with wolves.

howling wolf

Hang out with wolves at the Wolf Conservation Center in South Salem, NY, just over the Westchester border. Each year on New Year’s Day, visitors can help Howl in the New Year while they enjoy hot beverages and learn all about these beautiful and endangered creatures.

11. Catch Disney on Ice when it skates into town.

See Mickey, Minnie, and a host of your other favorite characters when the Disney on Ice tour stops at Webster Bank Arena in Bridgeport for a few days in early January. Check the website for the full schedule.


12. Have a sleepover with the starfish.

Kids can enjoy group sleepovers at the Maritime Aquarium in Norwalk. Enjoy a light dinner an aquatic guided tour, aquatic games, snacks and crafts. Wake up to breakfast, a private seal show, and an IMAX movie to cap off the morning.


13. Go sledding.

boys sledding

Pull out your Flexible Flyer and get set for some downhill snow day fun. Once there’s enough of the white stuff on the ground, Fairfield’s parks open for sledding. Find the best hills in the area in our guide.


14. Hit the ice with your skates.

Go ice skating at the Dorothy Hamill Skating Rink in Greenwich, or find another rink in our skating guide.


15. Lend a helping hand.

Give back to the community on Martin Luther King Jr. Day in mid-January. Learn more about volunteer opportunities in the Fairfield area.

16. Celebrate MLK.

The Bruce Museum in Greenwich invites families to participate in its annual Martin Luther King Family Day. The event commemorates the legacy and work of Dr. King, and involves educational activities, music, and other performances. Activities are free with museum admission.

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17. Wear your winter best to the children's ball.

winter children's ball

For the very popular Winter Wonderland Children’s Ball, held at Stepping Stones Museum in Norwalk in late February, kids are invited to dress in their party best for an evening of wintry celebration featuring dancing, a life-sized igloo and snow globe, winter crafts, and full access to all the exhibits in the museum.

18. Bounce away your cabin fever.

When the temps drop outside, keep your kiddos active indoors at Pump It Up Norwalk, where they can bounce around to their hearts’ content on the center’s giant inflatables. Check nymetroparents.com/calendar for details on the center’s upcoming drop-in sessions and special events like Parents’ Night Out and Sensory-Friendly Jump sessions.

19. Watch a sensory-friendly movie.

kids watching movie in theater

If you have a family member with sensory issues, opt for a sensory-friendly movie matinee where the lights stay up, the sound is turned down, and audience members are encouraged to get up and make as much noise as they please—find more info here.

20. Have a dino-mite winter break at the Peabody.

Kids can explore the prehistoric era during their Presidents Week school break in mid-February when the Yale Peabody Museum of Natural History in New Haven hosts Dinosaur Days.

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