8 Connecticut Towns with Real Holiday Spirit Last Updated: November 2023

No one dresses up for the holiday season quite like Connecticut. To find a few of the towns that show particularly scenic levels of festive spirit, we consulted the photo book, A Connecticut Christmas by Caryn B. Davis. We’re sharing some of her photographs that we think perfectly capture the charm of Connecticut and the warmth of the holiday season!


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A Cornwall Christmas Card

Within a short drive of some of the state’s busiest Christmas tree farms, West Cornwall is home to one of the most picturesque sights in Connecticut, the West Cornwall Bridge. Whether you walk or ride through, the bridge is one of a handful of covered bridges still left in New England. Stop to pick up a souvenir (or a Christmas gift or two!) at Cornwall Bridge Pottery or extend your visit to this pretty region with a stay at the Falls Village Inn in nearby Falls Village.

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Gift Shopping in Chester

Down along the southern portion of the Connecticut River, the sweet town of Chester lights up during the holiday season. Don't miss their annual holiday market and tree lighting celebrations. Stroll its Main Street boutiques, art studios, restaurants and more, usually brightly decorated for the season. Be sure to grab a meal at the Pattaconk Bar & Grille when you visit. Or, feel right at home while sampling local craft beer at the charming Little House Brewing Company.

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No Grinches in Greenwich

A visit to the town of Greenwich along Connecticut’s southwestern shoreline is a must-do during the holidays. In addititon to top name shops and local boutiques for everyone on your list, the family can enjoy the annual Reindeer Festival to keep everyone in the spirit. Make a reservation at the luxury Delamar Greenwich and enjoy a gourmet dinner at l'escale. You can even get here in less than an hour from New York City via Metro North train.

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In the Litchfield Spirit

This year, Newtown's Holiday Festival features virtual and in-person events including a scavenger hunt, bedtime stories with Santa, Festival of Trees, and lots more family fun. Nearby, check into The Litchfield Inn and have a bite at the Village Restaurant overlooking the town green. Plan to include a visit to one or more of the area’s Christmas tree farms, many of which offer tractor rides and hot cocoa too (seasonal).

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New Haven's Festive Sidewalks

The lighting of the Christmas tree on the famed New Haven Green just after Thanksgiving is always a big event for the Elm City. In fact, throughout the season, you’ll find holiday happenings such as free horse and carriage rides through the city and roving carolers to get you into the spirit. Pick up a few gifts at the Shops at Yale and reward yourself with a sweet treat from Libby’s Italian Pastry Shop.

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See the Lights in Meriden

Not far from the holiday hustle and bustle of New Haven, you’ll find the annual Festival of Silver Lights display in Meriden’s Hubbard Park. After dark, half a million white lights and illuminated character scenes come to life as you wind your way through this suburban park in a car or on foot. And it’s all free, through the month of December. Stock up on locally made seasonal sweets at Thompson Chocolate before you visit.

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Looking for the Charm in Essex

When snow covers the town of Essex, it looks like a New England picture postcard. But even without snow, you’ll find this lively and historic town celebrating the holidays with downtown strolls and house tours (watch the calendar!) Start your gift shopping at Toys Ahoy and grab a night (or a bite) at the Griswold Inn.  Essex is also home to the Connecticut River Museum which hosts the annual Holiday Train Show, a family favorite.

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Magically Mystic

Although it’s most popular as a destination for summer visitors, the town of Mystic literally lights up during the holiday season. From Santa’s arrival after Thanksgiving in a parade of colorfully-lit boats to Mystic Seaport Museum's Lantern Light Village to shopping at Olde Mistick Village, be sure to keep an eye on the calendar for all of the events and celebrations coming to Mystic for the holidays.

If you liked this tour of Connecticut’s holiday towns, check out Caryn B. Davis Photography or follow Caryn on Instagram at @carynbdavis. And be sure to check the CTvisit Events page regularly as new holiday celebrations for 2023 are continually being added.