5 of Connecticut's Prettiest Towns

TIMOTHY STARKEY HOUSE, 1720, NOW ESSEX COFFEE AND TEA COMPANY

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OK, on to the post. 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.

the single greatest loss of American shipping

the single greatest loss of American shippingand for being cute...by the mouth of the CT River where it meets Long Island Sound

Some highlights of a trip to Essex might be: The Connecticut River Museum, RiverFest Cruises, the Griswold Inn, the restaurants and shops all along Main Street and nearby streets (best for little gifts and treats or a more "curated" selection of antiques), Riverview Cemetery, the Essex Historical Society, The Essex Steam Train and Riverboat, and Ivoryton Playhouse. But the best thing about Essex might just be walking down Main Street (note: typing "Main Street, Essex" into your GPS will put you in Centerbrook; when you're about to drive into the water, and the dividing line down the road is painted red, white, and blue, you're in the right spot) and admiring the cute.

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.

When In Kent

JUST A GUITAR STORE. BECAUSE IT'S KENT.

The Size of Connecticut is about, as the header says, local destinations off the beaten path. This post is not about that. In fact, out of all the Town Center Strolls I've posted so far, Kent (along with Mystic) is possibly the most traveled. But sometimes one finds oneself in extremely popular destinations, and I couldn't let the opportunity for a blog post pass me by.

Kent used to intimidate me. The town, with a population of under 3,000, felt sophisticated yet rustic, blending the exclusivity of an upper-class suburb with the insularity of a small village. It always seemed that the sign at the town line reading "Kent Welcomes You" was not really directed at me.

These days I am not at all intimidated by Kent. It's a bit like the way objects which seem huge when you are small are revealed to be disappointingly medium-sized when you grow taller. The welcome sign is probably not for me, and I don't mind.

The thing is, Kent mostly just got lucky. It has a lot going for it: the preservation of Bulls Bridge, one of just a few covered bridges left in Connecticut; a stunning natural setting, full of steep hills and lush greenery; and a reputation for some of the best fall foliage in New England. It's home to two state parks, Kent Falls and Macedonia Brook. And the Appalachian Trail runs through it, meaning scruffy backpack-laden people who look like they just crawled out of the woods (because they just crawled out of the woods) co-exist, occasionally uneasily, with locals and New Yorkers weekending in the one part of the Connecticut countryside where they won't have to encounter people who don't care about New York. It also has self-consciously casual restaurants and oh-so-curated shops and numerous galleries, and there is art everywhere.

But as we all know, the lucky one is not always the best one, or the most deserving, or even the prettiest. Still, there's nothing you can do. You will go to Kent, because you can't not go there. Everyone goes there.

Now, I'm not saying there's anything wrong with Kent. I'm just suggesting that if you go there, don't let anyone tell you this is all northern Litchfield County has to offer. Take the opportunity to visit some of the less-traveled towns and villages of this beautiful area. The Secret Corner site is excellent if you want to plan what to do, and I have some ideas in my Litchfield County section as well. (Oh, and a word of warning to any drivers or cyclists who don't want to be surrounded by motorcycles on the lovely country roads: go during the week if at all possible.)

JUST A CPA'S OFFICE. BECAUSE IT'S KENT.

THE NEXT TRAIN WILL ARRIVE AT...OH YES, NEVER.

ART IS EVERYWHERE IN KENT. (THIS IS BY PETER WOYTUK.)

THE LIBRARY WAS HOLDING A TEMPTING BOOK SALE WHEN I TOOK THESE PICTURES.

THE SWIFT HOUSE DATES FROM THE 1780s.

THESE GUYS COULD PROBABLY BUY AND SELL YOU.

JUST A GARDEN DESIGN BUSINESS. BECAUSE IT"S KENT.

IN THE KENT VILLAGE BARNS SHOPPING CENTER.

FOREIGN CARGO ("A FASCINATING JOURNEY IN SHOPPING")

THE PRIMITIVE HOME

J.J. GROGAN'S ("PURVEYORS OF FINE THINGS")

WHERE RAILROAD STREET ENDS.

A Quick Walk in Milford

Milford is technically a city, but its walkable center feels more like a small town.

Like Clinton, Milford is a place many people come to shop. The Connecticut Post Mall, and the concentration of strip malls and big box stores along Route 1, mean roads in that area are often horribly congested. But a few minutes away there is another Milford, where historic bridges are decorated with flowers, little waterfalls spill into rivers and ponds, and ducks swim happily everywhere. The leafy, monument-studded Broad Street Green is the second longest town green in Connecticut. (The longest is, confusingly, in New Milford, though both of those seem shorter to me than Lebanon's endless meadow of a town green.)

Many years ago, I used to spend a lot of time in Milford. Back then, no one seemed particularly thrilled to be spending time in Milford, but that's been changing for a while now. The city hasn't lost its old-fashioned feel - just look at the duck pond and the little storefronts on the small streets that curve between the train station and the river - but it's gained a new kind of energy. Maybe that's simply a result of Fairfield County's population overflowing to the east in search of slightly less expensive housing. Whatever the reason, for the moment it strikes a very pleasant balance - not yet obnoxiously gentrified, just a bit brighter and shinier, like all those ducks are finally lining themselves up into a row.

Main Street, Clinton

I would guess that to most people in most parts of Connecticut, the town of Clinton is synonymous with Clinton Crossing, the outlet center on Route 81. (And if the recorded welcome messages in multiple languages that you hear as you walk along the center's "sidewalks" are anything to go by, that probably holds true far beyond Connecticut as well.)

I will admit to spending an embarrassing amount of time at Clinton Crossing, but if you think - as I once did, years ago - that its stores are the only reason to visit this shoreline town, you are mistaken.

Take a walk down Clinton's Main Street (East and West Main meet above the Indian River, which winds its way past the town's beach and into Long Island Sound.) You'll see the Elisha White House, a.k.a. Old Brick, built in 1750 and now used by the Clinton Historical Society. Witch hazel, used "by early settlers for medicinal purposes" and "by Unilever/Ponds, a corporation that dominated manufacturing in Clinton for decades," grows in the garden in the back. 

You'll also pass all the usual small-town staples: coffee house, ice cream parlor, appliance store, post office, pizza place.

One thing I always notice every time I'm in Clinton is how much history and eccentricity remains. Some other towns might have demolished this little house and replaced it with a drab brick rectangle of an office building by now, but here it still stands proudly.

.The 1791 Adam Stanton House was built "by a wealthy, striving merchant-businessman."

The store sold "a wide array of dry goods from baskets to salt to tools and tea."

The Academy was founded in 1801 as, essentially, a prep school.

Higher education was big around here long before that, though; the Reverend Abraham Pierson, who was minister of the Congregational Church in Clinton beginning in 1694 (back when Clinton was still part of Killingworth) attended Harvard and helped found the school which would later become Yale.

(Speaking of New Haven - did I mention pizza?)

The current Congregational Church building, almost obscured by summer trees and standing high up on a hill, was built in 1837.

Everywhere you look in the center of Clinton, you'll spot some little plaque or monument. On a recent walk through town I noticed for the first time a little waterside gazebo at Clinton Landing, behind the Town Hall, and the site of the goldsmith shop of Abel Buell. 

Though I love the shoreline year round, summer is the time when this region comes alive. Merchandise is moved out of stores and onto sidewalks, people emerge from indoors to be near the water, and flowers bloom everywhere.

Summer is also when the flags appear. Suddenly, one day, they are everywhere (large, small, draped over doorways, hanging from utility poles on the main roads, stuck into flower pots) and weird, obstinate little Connecticut transforms into classic, jubilant America.

Laurel City

Winsted is a city located within the town of Winchester, much like Willimantic is a city within Windham and Groton is a city within Groton.

If you live in Connecticut long enough you'll get used to such things, but the first time you discover one of these little cities wearing a town like an overcoat, your mind will be blown.

I remember when I first drove through Winsted. It was perhaps seven years ago, shortly after I moved back to Connecticut, and I was perplexed by what I thought was a singular (and uniquely weird) municipal and geographical arrangement.

But that's not what I remember most about my first impression of Winsted. What struck me initially was the unusually wide main street, not the norm for a Connecticut town settled in the mid-18th century. As it turned out, the street had not originally been laid out in such an open, almost Midwestern manner; it was widened to four lanes after the devastating floods of 1955 wiped away a great swath of downtown. Then I noticed the old mill buildings along the Mad River. (Is there a better-named river anywhere in the country? The world?) Here they made scythes, and hosiery, and clocks - a typical non-sequitur of a shopping list from Connecticut's manufacturing glory days.

Today in Winsted, as in other Connecticut cities, people are making - or trying to make - good use of those old brick mills and factories. There is still a long way to go, but I hope their efforts succeed. There's so much potential in that wide main street, the proud buildings that line it, and the little river - calm, for now - that runs alongside.