Connecticut Towns to Make Winter Break Memories Last Updated: December 2022

Meet the CT Ambassadors! is proud to partner with some of Connecticut’s most popular bloggers for ideas, insights and inspirations from the people who are lucky enough to call Connecticut home, like blogger Mommy Poppins.

Connecticut is well known for its New England summers and some of the most breathtaking fall foliage in the country. But the state does anyting but hibernate during the winter months. Explore all corners of the state's charming towns and wintry scenic countryside with these wonderful winter fun ideas from our friends at Mommy Poppins. Check out their Connecticut Winter Fun Guide for even more ideas. 

Find hospitality and history in Washington

With its picturesque towns, winter in Washington is much like you might imagine life in a snow globe would look. A visit to the Litchfield Hills area offers cozy and traditional New England pleasures like cozying up with a good book at the Hickory Stick Bookshop, voted best country bookstore by Yankee Magazine

The Litchfield Hills are home to several of New England’s prominent boarding schools - one of which is The Gunnery. Every Sunday evening The Gunnery’s Linen Rink opens its doors for family skate. The cozy and historic Gunn Memorial Library offers excellent family programs throughout the holiday season. 

The Institute for American Indian Studies Museum & Research Center’s award-winning Wigwam Escape room offers a unique twist with a historically-themed adventure for the whole family. Without using phones, clocks, tools, or written language you must solve the puzzle by relying on skills important to survival some 500 years ago. 

(Photo courtesy of the Institute for American Indian Studies Museum & Research Center)

Take in Cassatt and cross-country in Farmington

Connecticut has the winter sports scene covered. If cross-country skiing is your thing, we've got just the place—Winding Trails in Farmington. This full-service facility has all ages covered, from tots to teens, with a rental center, snack bar, and a toasty fire to warm your toes. 

Farmington is also the home of the family-friendly Hill-Stead Museum where works by such masters as Degas, Manet, Monet, and Cassatt are on display throughout the historic house, along with a collection of prints, photographs, and various decorative arts and furnishings. Nearby, the Stanley-Whitman House offers history, enriched, family-friendly programs all year round, including Colonial open hearth cooking.

(Photo courtesy of Winding Trails)

Celebrate yesterday and today in Mashantucket

As the largest resort casino in North America, Foxwoods Resort Casino provides entertainment for every member of your family. The world-class resort houses 2 family-friendly indoor pools, video games arcades, bowling, a zipline, virtual reality experiences, escape rooms, a pottery painting studio, and more. In other words, kid heaven. And, if that doesn’t sound sweet enough, there’s also a Sugar Factory with its signature over-the-top lineup of candy-inspired mocktails and cocktails. 

Before you head home, make sure to check out the Pequot Museum featuring Native American history. This 308,000 square foot complex has a permanent exhibit, a restaurant, and a research center. What young guests remember most are the multi-sensory dioramas that depict the Mashantucket Pequot Tribe and the cultural history of the eastern woodlands. 

Experience arts and ice adventures in Westport

Connecticut has the good fortune of having some top-notch outdoor skating rinks, but only one of them has sweeping waterfront views of the Long Island Sound. At the Westport Police Athletic League Rink, we highly recommend strapping on your skates at sunset and watching the lights twinkle on the water. 

On Thursdays, head over to the Westport Winter Farmer’s Market on Sylvan Lane. Housed in the warmth of Gilbertie’s Herb Gardens' greenhouses, this market has over 30 vendors and fun family activities. 

Westport has a long history of being home to all kinds of artists from performing arts to visual arts. The Westport Country Playhouse provides its Family Festivities Series throughout the winter.  If visual arts are more your thing, the MoCA Westport is featuring a Human Rights teaching exhibit.

Enjoy slopes and slices in Middlefield & New Haven

Located about thirty minutes north of New Haven, you will find Besek Mountain; more commonly known as Powder Ridge Mountain Park and Resort. There is nothing quite like the cold air brushing against your cheeks as you fly down the mountainside. Thankfully you can find that thrill in Connecticut without ever putting on a pair of skis. Powder Ridge offers two-hour passes to its specially groomed tubing trails

Warm yourself up with comfort foods, Connecticut style- aka burgers and pizza. Known as the birthplace of the American hamburger and for its iconic pizza places, New Haven is definitely a kid foodie’s paradise. You can get a taste of some of the most famous pizza in America at Pepe’s or Sally’s. The Elm City also boasts an indoor ropes coursewonderful art galleries, and so much more. Check out the complete list of Mommy Poppins’ 25 Things for Families to do in New Haven for more.

More Ideas the Kids Will Love

The fun doesn't stop there. Check out the guides below for endless winter break thrills.