Connecticut’s Best Towns and Villages

Road trip through history and shop by the sea

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Something special happens in Connecticut. Park the car, stroll main street, and feel the decompression begin. Main Street America? We invented that. Town greens? Those come standard here. White picket fences and American flags? Got those covered, too. The charm of Connecticut can be found in its small towns and main streets. Explore unique shops and galleries, get immersed in the café culture and soak in the authentic life. There are no wrong turns.

Fairfield County

Start your country getaway in Greenwich, the state’s coastal southwest corner. Greenwich Avenue, the “Rodeo Drive of the Northeast,” is packed with boutiques, jewelry stores, design showrooms, chic cafés and art galleries. Summer music series, art shows and Shakespeare on the Sound attract visitors and locals to the heart of the village.

Up the coast, Westport welcomes guests to a picturesque waterfront setting. Start at the Westport Historical Society inside the 1795 Wheeler House. More than 200 homes here date back at least 100 years, and the historic downtown features a mix of unique shops and luxury brands. This former artists’ colony is still a vibrant cultural center with the Westport Country Playhouse and the Levitt Pavilion playing to packed houses.

Greater New Haven

As the first planned city in America, New Haven boasts a skyline that mixes Gothic towers with modern high-rises.Yale University gets much of the credit for New Haven’s civic pride, and visitors energetically browse the boutiques and bookstores that cater to the Yale intelligentsia. Atticus Bookstore and Café on Chapel Street makes a great jumping-off point. Work your way down York Street through Yale to Broadway. Circle back to campus to visit the greatly expanded Yale Art Gallery, the Yale Center for British Art and the renowned Shubert Theater.

The seaside town of Madison makes a great place to overnight this time of year. The town green hosts arts and crafts fairs, antiques shows and performing arts during warmer months. Main Street is anchored by a historic movie house and has plenty of great spots to grab sodas, sandwiches and sweets. Visitors also can enjoy the Sculpture Mile, where the work of local artists is dotted along the street. Its proximity to Yale makes Madison bookish, too, as visitors discover at RJ Julia Independent Booksellers.

Another quintessential New England town nestled along the shoreline, Guilford branches off from the largest town green in the state. Five museums set up shop inside historic homes—the Henry Whitfield State Museum is the oldest stone house in New England, with many artifacts of 17th century Puritan life on display. The cute part? Visitors can soak in all the period pieces while perched on a Segway. Shoreline Segway offers guided tours through the entire time capsule.

Litchfield Hills

Not all of our postcard-perfect villages have coastal views. Connecticut’s hills and valleys make picturesque backdrops for charming towns as well.

Centrally located in the scenic hills of northwest Connecticut, Litchfield presents a lovely picture of Colonial life. Walk up and down North Street and South Street, searching for a treasured antique along the way. The Congregational Church on the town green is one of the most photographed in the state. Mingle with the locals at the highly acclaimed West Street Grill, where you might find a famous personality.

The colorful town of Kent is a small-towner’s dream. The pre-Revolutionary War village hugs the Housatonic River, which makes the easy-to-walk public corridor a scenic experience as well. An idiosyncratic mix of shops occupies 19th century homes. Delighted visitors might uncover the garden statuary or antique inkwell they’ve been searching years for. Visit the vast Morrison Gallery with exhibits by internationally known artists.

Mystic Country

Mystic Country offers a delightful combination of shoreline towns and inland beauties nestled in the “quiet corner” of the state. Mystic preserves an authentic snapshot of 19th century coastal life in New England. This small shoreline village has boat rides during warm weather from Mystic Seaport, as well as an assortment of unique shops and fresh seafood. The neighboring village of Stonington features the Old Lighthouse Museum, charming shops, art galleries and cozy inns.

Just between us, Putnam is Connecticut’s best-kept secret. Long hailed as an antique-hunter’s dream destination, this charmer feels as collectible as its wares. Every store in the walkable town center presents a new treasure waiting to be discovered. Weary shoppers get their second wind at restaurants and coffee shops along the Quinebaug River, which meanders through the downtown district.

Connecticut River Valley

In Connecticut’s central valleys, history goes back centuries. Inns have operated here since the 1700s, Main Street houses proudly fly flags, and homeowners and shopkeepers compete for the best window boxes.

Begin in Essex at the Connecticut River Museum, where the state’s maritime legacy is on display, along with the Turtle—a replica of the first submarine built for one person. Catch the trolley that loops through town at a leisurely pace and plot a route to explore on foot. Romantic getaways are a natural here, aided in part by the roaming seasonal flower cart in search of lovers on Main Street.

In Wethersfield, visit artifact-rich museums, quaint shops and sidewalk cafes nestled among tree-lined streets. Public gardens and farm stands honor the area’s agricultural history. And Connecticut’s largest historic district includes more than 50 homes built before the Revolutionary War. Some can even claim that “George Washington slept here.”

Get a Room

B&Bs and historic country inns exemplify the quintessential Connecticut getaway. The Griswold Inn, front and center on Main Street in Essex, has welcomed guests since 1776. Others, such as Water’s Edge Resort & Spa in Westbrook, offer rooms with waterfront views.

This itinerary is compliments of the Connecticut Office of Tourism.

At A Glance

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