Winter Festivals in CT: Heartwarming Ways to Enjoy the Season

There’s a magic in the air when there’s a crispness in a breeze with the tinge of snow on the horizon. It’s what helps make Connecticut so special during the winter.

Aside from the million reasons it’s incredible in the warmer months, of course

What better way to celebrate the new season than to attend one of the many winter festivals in CT with lots of fun activities? It allows families to get together, take a stroll wrapped in warm scarves, and drink some hot chocolate.

There’s always something for everyone:

The little ones can enjoy face painting
Mom can relax in a carriage ride
Dad can be in awe of ice sculptures
And the whole family can enjoy pictures with Santa

The decorated streets and incredible foods stationed around make for fantastic afternoons.

The top winter fairs and festivals in CT

There are many holiday-specific festivals around the state.

Is December not a good time for you to get away?

Fear not: You can enjoy these festivals throughout winter.

Holly Berry Festival

One of the first winter festivals of the season, on November 22nd, take your family to the Holly Berry Festival at the Sacred Heart Academy. The event offers free admission to all.

Kids can have their photo taken with Santa, and the parents can enjoy the baked goods, along with the pasta dinner and other fun activities.

Greenwich Holiday Stroll Weekend

You and your loved ones will not want to miss the Greenwich Holiday Stroll Weekend.

You can:

Hop on a complimentary carriage ride
Witness a live nativity scene featuring real animals
And relax to holiday music performances

If you’re someone who likes to see lots of different things, you can check out the ice carving and test some of the food from the local trucks. The best part is the festival takes place Saturday, December 2 from 10 a.m. to 6 p.m. and Sunday, December 3 from noon to 5 p.m. in downtown Greenwich. That means you can do some holiday shopping while the kids are checking out the events. Local businesses even offer discounts for shoppers to share the holiday magic!

This annual event kicks-off the Greenwich Reindeer Festival, which lasts through December.

Kent Gingerbread Festival

The annual Kent Gingerbread Festival returns in December.

Shuffling along Kent’s main street from store to store, admiring holiday gingerbread creations, is about as quaint as the holidays get.

The Tunnel of Lights and Winterfest

At East Windsor’s Winterfest and Tunnel of Lights, establish a new holiday custom while riding in a vintage trolley vehicle.

Sing holiday carols while the trolley glides through a tunnel of shimmering lights. After that, visit the tourist center to see the model trains and lovely seasonal decorations. Santa will be waiting for you, with a little something for every visiting kid. Most Friday, Saturday, and Sunday evenings in December from 5:00 p.m. to 9:00 p.m. are festival nights at the Connecticut Trolley Museum.

This is one (of many) top Christmas lights displays across Connecticut.

Festival of Trees and Traditions at Wadsworth Atheneum Museum of Art

What started as a fundraising event in 1974, the Festival of Trees and Traditions at Wadsworth Atheneum Museum of Art has turned into a gathering to celebrate the holiday season.

Visitors can enjoy the works of local artists and businesses and donate decorated trees and wreaths. All donations will be displayed at the galleries, showcasing the generosity of community members.

The festival will take place from December 1 to December 3, and then again from December 6 to 10 at 600 Main St., Hartford, CT.

Newtown Holiday Festival

What says Christmas more than a holiday trolley ride, gingerbread house contest, and a festival of trees? Head over to Newtown to celebrate the holiday season with fun for the whole family. Your kid will likely be most in awe over the Polar Express or the Nutcracker Suite Ballet. There’s also a historic house tour for everyone to see the beauty of history and timeless decorations

The Newtown Holiday festival takes place on Saturday, December 3 from 11 a.m. until 4 p.m. at 25 Main St., Newtown, CT.

Bethlehem Christmas Town Festival

Bethlehem’s Christmas Town Festival is a highly anticipated holiday event for locals. Families can enjoy such winter activities as:

Ride the Christmas Town Train
Get their faces painted
Hop on a hayride
Enjoy the cookie sale
Relax to live music
And check out the craft and food vendors

This winter festival runs on Friday, December 1 from 5 p.m. to 10 p.m. and Saturday, December 2 from 8:30 a.m. – 4 p.m at Town Green, Junction of Rte. 61 and Rte. 132, Bethelehem, CT.

Winterfest at Mystic Aquarium

The festive spirit fills Mystic Aquarium from December 26 to January 1. Watch as artisans fashion incredible ice sculptures, elves play with the animals in the pond, and take in some local entertainment. When you create your very own snowflake creation, you’ll be able to bring a bit of Winterfest home with you.

Winterfest at Ski Sundown

For Winterfest 2023, a celebration of winter enjoyment, visit Ski Sundown! Join in celebrating the winter season by donning your favorite winter costume, silly hat, or helmet cover! Anyone with a lift ticket or pass from Ski Sundown is welcome to attend this free event!

The festivities on January 21 will include:

Meeting Olaf from Frozen
Live music
And live ice sculpting demonstrations

Purchase your lift tickets for today in advance online. Anyone having a lift ticket or pass from Ski Sundown is welcome to attend for free!

Chester Winter Carnivale

Chester Winter Carnivale may be the most highly attended of the winter festivals that take place in Connecticut. Attendees can watch a tractor parade, shop the local gallery, and check out the local specials. One of the most highly anticipated events is the Chilly Chili Cook-off, where guests can witness a good ole ingredients throw-down. After their stomachs are rumbling, they can check out many street eats and treats available.

Ice carving, face painting, and other entertainment will also be available. The festival takes place on Sunday, February 18 from 10 a.m. to 4 p.m. in the Chester, CT center.

It’s one of the best things to do in Connecticut in February, for obvious reasons.

We hope you have a great start to your winter festivities!