9 Winter Festivals In Connecticut That Are Simply Unforgettable

There are so many ways to celebrate the crispness of the air and the impending arrival of snow in Connecticut every winter, but there is something truly amazing about attending a festival. Face painting, carriage rides, ice sculptures, pictures with Santa, fabulous street eats, and tractor parades – yes, even tractor parades! – are some of the magnificent things that happen during winter in Connecticut. These celebrations occur at a variety of times throughout winter, so you’ll have plenty of opportunities to attend them all! Here are some of the coolest winter festivals in Connecticut this season that you definitely don’t want to miss.

1050 Washington Blvd, Stamford, CT 06901, USA

Holiday Stroll/Facebook

The all new Holiday Stroll at Mill Park in Stamford is a gorgeous, illuminated showcase that captures the magic of the season in the most brilliant way. The spectacular walk-through experience is interactive and captivating, featuring a 30-foot Christmas tree, synchronized music, 3D ornaments, and incredible light displays. For the adults: a Winter Beer Garden awaits! Plus delicious food vendors serving up festive and fun eats for the whole family. For the kids: carnival rides and some of their favorite holiday treats, including cider doughnuts and hot chocolate with marshmallows.

This event typically runs Thanksgiving to Christmas Eve. Learn more about the Stamford Holiday Stroll on their website.

Fairfield Christmas Tree Festival

Every year the historic Burr Homestead in Fairfield is transformed into an extraordinary Christmas display with each room beautifully decorated and full of festivity. The holiday boutique will be open for those who want to do a little shopping and Santa is available for photos with the kids. There are also a few special events planned like Holiday Hip Hop Night and a Nutcracker Sweet Tea.

Editor's Note: After 40 years of kicking off the holiday season, the Fairfield Christmas Tree Festival lit up its trees for the last time in 2021. In its many years of celebration, the festival raised millions of dollars for local charities and created lifelong memories for countless families. It will be greatly missed in the years to come.

Advertisement

Newtown, CT, USA

Newtown Youth and Family Services

A holiday trolley ride, gingerbread house contest and festival of trees make this holiday festival in Newtown an enchanting place to visit. There is also a polar express for the kids, historic house tours, and the Nutcracker Suite Ballet. Newtown knows how to pack a whirlwind of activity into one day! The Newtown Holiday festival typically takes place the first week of December.

Learn more about this family-friendly festival via the Newtown Family Services website.

Advertisement

Wadsworth Atheneum Museum of Art, 600 Main St, Hartford, CT 06103, USA

Facebook/Wadsworth Atheneum Museum of Art

The Festival of Trees and Traditions was started in 1973 as a fundraising event. Local artists, community members and businesses donate decorated holiday trees and wreaths to be put on display in the galleries. It is quite an extensive collection of holiday cheer shining all in the same space! This festival typically takes place the first week of December every year.

Learn more about this unique festival via the Wadsworth Atheneum Museum of Art website.

Related Stories

Delight In A 100-Foot Christmas Tree During This Epic Holiday Festival At A Beloved Connecticut Amusement Park

A LEGO Festival Is Coming To Connecticut And It Promises Tons Of Fun For All Ages

Paid Content Brick Fest Live

Marvel At Ice Sculptures, Reindeer, And More At Connecticut's Wintertide Festival This February

Bethlehem, CT, USA

Facebook/Bethlehem Christmas Town Festival

The Christmas Town Festival in Bethlehem is quite a celebration, and it all starts with a ride on the Christmas Town Train. Other events include face painting, hay rides, a cookie sale, live music and craft and food vendors. There is a whole lot to do and see at this exciting winter festival which typically runs the first week in December.

Learn more about the Christmas Town Festival on the official website.

Connecticut Trolley Museum, 58 N Rd #9606, East Windsor, CT 06088, USA

Facebook/Winterfest and the Tunnel of Lights

Start a new holiday tradition aboard a historic trolley car at the Winterfest and the Tunnel of Lights in East Windsor. The trolley will pass through a tunnel of sparkling lights as your ride along singing Christmas carols. Afterwards you can head into the visitors center which has beautiful holiday decorations and model trains to view. Meet up with Santa and he will have a small gift for each child. The festival is at the Connecticut Trolley Museum and typically run every weekend from Thanksgiving through the end of the year.

Learn more about Winterfest on the Connecticut Trolley Museum website.

Putnam, CT, USA

Facebook/Saybrook Point Inn, Marina & Spa

The Fire and Ice Festival is a unique way to warm up on a chilly day. The only one of the Connecticut winter festivals to offer both a fire bar and a sculpted ice bar, this is one unique way to celebrate the cold weather. There will be plenty of local food, beer and wine offered along with demonstrations of ice sculpting and woodworking. There will also be opportunities to take that classical winter carriage ride. The Fire and Ice Festival is typicaly held around Valentine's Day, but times vary.

Learn more about the Fire and Ice Festival, visit the City of Putnam website.

Mystic Aquarium, Stonington, CT 06355, USA

Facebook/Mystic Aquarium

The last week of Deecember, Mystic Aquarium comes alive with holiday cheer. There are different events scheduled every day to celebrate the season. Watch as artists create amazing sculptures out of ice, elves frolic in the water with the animals and enjoy local entertainment. You can take a piece of Winterfest home with you by crafting a snowflake masterpiece of your very own.

To learn more about Winterfest, visit the Mystic Aquarium website.

Advertisement

Chester, CT, USA

Facebook/Chester CT Winter Carnivale

The streets of Chester fill up completely with the arrival of the Winter Carnivale - this just might be the most highly attended of CT's winter festivals! This event is packed with fun activities for the whole family. Watch a tractor parade or shop the local gallery and shop specials. You definitely won't want to miss the Chilly Chili Cook-off and there are plenty of other street eats and treats available. There will also be ice carving, face painting and other entertainment. The Chester Winter Carnivale typically takes place every year in February.

Learn more about this local festival via the City of Chester website.

While this isn’t a complete list of all of the coolest winter festivals in Connecticut, these are a great place to start! Do you have any other favorite things to do in winter in Connecticut? Are there any other winter festivals that should be added to this list? Let us know so we can check them out!

Still looking for more things to get you in the Christmas mood for this season? Our holiday bucket list will get you into the holiday spirit in no time.