There are many towns that could be called the prettiest in the Constitution State, depending on your taste and criteria, so I want to explain how I made this list. All of these towns have something about them that screams (politely, of course) classic Connecticut and classic New England. They have all maintained their historic character and although they have changed to varying degrees with the times, they have not been spoiled by the clutter of modern life. They're not so small that you can see everything in a few minutes, nor so big that they feel like cities. They have walkable centers where there's plenty to do and see, and they're also a short and easy drive from other attractions. These are not the towns that make you say, "It would be so nice to live here;" these are the towns that make you say, "People live here?!" These places are physically beautiful, whether you look at their architecture or their natural settings. A visitor dropped in one of these towns with no warning or plan would a) instantly reach for their camera, b) be able to entertain themselves immediately, and c) have no problem quickly developing an itinerary for a few hours or a long weekend.
Essex
Essex is best known for being the target of the British raid that led to "the single greatest loss of American shipping" in the War of 1812, and for having once been named the best small town in America. Located at the picturesque junction of the Connecticut River and Long Island Sound, Essex is made up of three villages: Ivoryton, Centerbrook, and Essex Village. For the most part, when people talk about how adorable this little port town is, they're talking about Essex Village. And it is pretty freaking adorable - from homes to businesses to municipal buildings to street signs, everything here is nautical and twee yet somehow understated too. Surprisingly, given how many times a day tourists must pause on the sidewalk to photograph their houses, the residents of Essex always seem to be smiling and friendly when you pass them on the streets.
For an equally adorable but more down-to-earth Connecticut River town, head north to Deep River. (North of Deep River is Chester - more on that below.)
Stonington Borough
So, this is a tad confusing. There's Stonington, the town in southeastern Connecticut on the Rhode Island border. There's also North Stonington, the town just north of Stonington, but don't worry about that for now. And then there's Stonington Borough, located within the town of Stonington. This mile-long peninsula ends at a point (called the Point) from which you can see the watery borders of three states (CT, RI, and NY.) Stonington Borough (I'm just going to call it Stonington from now on) manages to feel like an authentic fishing village and a watercolor rendering of a coastal paradise, both at the same time. It would be an exaggeration to call this place a hidden secret, but it is vastly under-appreciated, and although it's now starting to appear on Best of New England-type lists, you might feel like you stumbled upon it thanks to the best wrong turn ever.
Stonington attractions include: Shopping and dining on and around Water Street, as well as at the Velvet Mill, the Old Lighthouse Museum, the Captain Palmer House, the town dock, DuBois Beach, Dodge Paddock/Beal Preserve, Saltwater Farm Vineyard, Stonington Vineyards, and Stonington Point. But don't forget to simply wander Water Street and Main Street, past Cannon Square and up and down all the little time-warped residential cross-streets between them.
If you get tired of Stonington, which might not be physically possible, you're just a few minutes' drive from two tourism powerhouses: Mystic, also partly located within the town of Stonington and home to the famous Seaport and Aquarium, and Westerly, RI, with its very popular beaches.
Litchfield
Litchfield is what people who have never been to Connecticut think of when they think of Connecticut. Preppy and pristine, with a town center consisting of tasteful white and brick buildings and a sedate green, you might mistake Litchfield for one of those little places where everything looks lovely but nothing ever happens. But in fact, there's a lot to explore in and around the town that lends its name to the Litchfield Hills.
While in Litchfield, you might visit: The Tapping Reeve House and Litchfield Law School, Haight-Brown Vineyard, the restaurants and stores at the center of town (this is technically a borough within the town of the same name, as Stonington is) White Memorial Conservation Center, and Topsmead State Forest.
Any drive to or from Litchfield will be a scenic drive. Head for a nearby town like Kent, New Milford, New Preston, or Norfolk (or pick a random one, they're all cute, I promise.) Along the way, watch out for covered bridges, cows, and dramatically rolling farmland that will make you struggle to keep your eyes on the road. For especially astonishing views, drive around Lake Waramaug. To experience a more bustling part of the Berkshires, go north to Great Barrington, MA. All the towns listed here are beautiful year-round, but if you go to Litchfield County in the fall, be aware that everyone else will be going there too - and for good reason.
Chester
Chester calls itself a "small rural town" with roots in mills and shipbuilding, but that description doesn't prepare you for how European this charming Connecticut River Valley town feels. Narrow, hilly roads converge at the curiously curved Main Street, where brightly painted buildings house boutiques, galleries, and restaurants, and the little Pattakonk River swirls below. Chester is quiet, classy, and artsy - three adjectives that could describe many Connecticut towns. This one is unique enough that I had to include it here.
Some things to experience in Chester are: Chester Museum at The Mill, the Chester-Hadlyme Ferry, local marinas and lakes, and the Norma Terris Theatre.
Cross the historic Swing Bridge to find the postage-stamp sized town center of East Haddam, home to the Goodspeed Opera House and the Nathan Hale Schoolhouse. Gillette Castle and other nearby state are good spots from which to appreciate the natural beauty of this part of the state. Keep driving north and you'll reach Middletown (west of the River) and East Hampton (to the east), both of which offer their own array of sights and activities.
Wethersfield
This central Connecticut town where Washington rendezvous'ed with Rochambeau (yes, I've been listening to Hamilton ever since New York in November) is undoubtedly historic; it fights for the rank of oldest town in Connecticut, or "Ye Most Auncient Towne" in Connecticut, with nearby Windsor. Wethersfield is larger than the other places listed here, but the section sometimes called Old Wethersfield (essentially, the downtown) is village-sized. It conjures up storybook American scenes (you know, with sidewalks and lush green lawns and ice cream cones and stuff) with a particularly New England flavor.
Visitors to Wethersfield might stop at: The Webb-Deane-Stevens Museum, Heirloom Market at Comstock Ferre and the other stores and eateries nearby, Cove Park and the Cove Warehouse, the Ancient Burying Ground, the Buttolph-Williams House, and many other historic Wethersfield sites. You'll find many of these by simply walking the length Main Street and exploring Broad Street and other roads that look inviting. You'll be sure to pass perfectly preserved homes of eras past, and you'll want to stop and read the plaques on all of them.
Wethersfield is one of a collection of Hartford suburbs like Glastonbury, West Hartford, and Simsbury, that are more interesting and substantial than the word "suburb" implies. But the best way to extend a visit to this historic spot is to cross the town line into Hartford and take in the variety of cultures, cuisines, entertainment options, and landmarks of the capital city.
Photo by Johnna Kaplan