’Tis the season in Connecticut! From historic main streets and sparkling displays to vibrant cities with urban flair in every string light, holiday spirit can be found all across the state. Read on to discover some of Connecticut’s most merry destinations.
Chester
This charming rural town has fascinating nautical roots — a history you can still feel as you wander along the Connecticut River downtown. The iconic Chester Stars displays cast a warm glow all winter long, illuminating shops, art galleries, and cozy restaurants. Whether you’re attending one of their annual holiday events or stopping by on a quiet weekday, Chester’s dazzling lights and quaint vibe are sure to leave you enchanted.
Essex
While the Essex Steam Train is often thought of as the main attraction of this coastal town, there’s much to explore when it comes to holiday cheer. Declared one of the “American Merriest Main Streets,” according to NBC’s "Today,” Essex gives “festive” a whole new meaning. From community parades and colorful lights to riverboats and tours of historic homes, this town combines fascinating history with jolly celebrations. Don’t miss a visit to the Connecticut River Museum for the ultimate glimpse of the season through a historical lens.
Litchfield
Litchfield is known as one of New England’s and one of the most beautiful residential communities in the country. True to its reputation, Litchfield embraces an intimate, collaborative approach to winter celebrations. From its annual tree lighting and local artisans’ markets to intimate holiday concerts, Litchfield’s festive events are steeped in history and small-town charm, offering an authentic New England experience.
Meriden
Conveniently located in the center of the state, Meriden might seem like an unlikely contender for a holiday spirit roundup. However, the free Festival of Silver Lights at Hubbard Park proves this playful city deserves a spot on the list! Every evening through early January, Hubbard Park transforms into a sparkling spectacle with over 300,000 twinkling lights. The dazzling displays include animals, tree decor, and curious scenes both traditional and modern all artistically arranged around the park’s Mirror Lake and walkways. For a free, fun, and festive night of razzle-dazzle, head to the Silver City.
Mystic
Olde Mistick Village is charming year-round, with its bevy of local businesses in a walkable layout free of car traffic. In December, it transforms into a whimsical winter wonderland, complete with sparkling decorations and seasonal events. Nearby, downtown Mystic offers a different vibe, with its waterside side charm, markets, and iconic Mystic River Bascule Bridge. You won’t see the bridge move to allow vessels to pass through, but you may catch a glimpse of some boats adorned with string lights or wreaths.
Washington
Tucked in the rolling hills of Litchfield County, the town of Washington offers a peaceful and idyllic holiday escape. Stroll through the village streets that inspired the “Gilmore Girls” TV series draped with sparkling lights and festive charm. Explore seasonal events at iconic spots like the Mayflower Inn, shop for unique gifts from local artisans, or enjoy a meal at one of Washington’s local restaurants.
Wethersfield
Known as “Ye Most Ancient Towne” in Connecticut, Wethersfield brings American traditions to life like no other. Its historic district, filled with beautifully preserved homes and landmarks, becomes even more magical when adorned with traditional yuletide decor. Here you can find carolers strolling down Main Street, festivities at the Keeney Memorial Cultural Center and, on certain dates, horse-drawn carriages trotting dutifully down the streets. A trip to Wethersfield is like taking a step back in time with all the warmth and wonder of the season.
But wait – there's more!
We can’t possibly list all of Connecticut’s towns with winter happenings. Take a look at this list of holiday happenings and this list of winter events from CT Visit.
