5 Underrated Small Connecticut Cities

"PEACOCK ALLEY," NORWICH

Happy New Year, and welcome to a new type of post I've been wanting to incorporate into The Size of Connecticut. I had the idea to do a little series of "Top Fives," grouping five similar destinations, in the hope that it might help people looking for a particular type of place to go.

This first one is about some of the small (population-wise, though some are tiny in area as well) Connecticut cities that often fly under the radar of people in the Nutmeg State and outside of it. For the purposes of this post I'm defining city as a municipality that is incorporated as a city (in Connecticut, you can't always tell what's a city and what's a town without looking it up) and one that feels urban: these places are walkable, they're relatively densely populated and built up, they've historically been centers of industry (not just farmland), and they offer plenty of things to do, places to eat, and sights to see.


Norwich

Population: 40,493

The so-called Rose of New England, at the confluence of the Thames, Shetucket, and Yantic Rivers, is the place to go if you like to be surprised by dramatic architecture and topography. From the downtown area, with its hilly, one-way streets and unpretentious waterfront, to Norwichtown, where 18th and 19th century homes surround the town green, to the time-warped old mill village of Taftville, Norwich is as unexpected as its new peacock mural - painted on a set of alley stairs - would suggest. This city can seem a bit abandoned at times, but that's what lets visitors pretend they're the first to have discovered it.

Some other Norwich attractions are the Slater Memorial Museum at the Norwich Free Academy, the Leffingwell House Museum, the Veterans Memorial Rose Garden in Mohegan Park, the Spa at Norwich Inn, and several history-centered walking tours, including one dedicated to local hero-turned-villain Benedict Arnold.

New London

Population: 27,620

With only about five and a half square miles of land to its name, New London is tiny. But the Whaling City, located where the Thames River meets Long Island Sound, makes up for that by being saturated with what feels like more history per square inch than any other place in the state. It's also got more than its fair share of art galleries, coffee shops, and restaurants. Here, old-fashioned beaches and lighthouses meet military pride and an eclectic, artistic, diverse downtown. New London seems to constantly swing between downturn and revitalization, but you could say it's impressive the city exists at all, given that the aforementioned Benedict Arnold burned most of it down in 1781.

A few of New London's highlights include the Lyman Allyn Art Museum, the Custom House Maritime Museum, the Hempsted Houses, the United States Coast Guard Academy, Fort Trumbull State Park, the Old Town Mill, Monte Cristo Cottage, the Connecticut College Arboretum, Ocean Beach Park, the Historic Waterfront District Heritage Trail, and Whale Oil Row.

Middletown

Population: 47,648

Within Connecticut, Middletown's appeal is no secret (though residents of the state's corners who are less familiar with its center can be quite surprised the first time they stumble across this charming city.) But elsewhere, aside from the occasional "Most Romantic Main Street" award, Middletown is relatively unknown. Which is too bad, because this place - funky college town meets plucky New England city in a spot geographically fortunate enough to offer a plethora of activities for sporty outdoor types - should be on more people's "to visit" lists. The main attraction is the downtown area, situated along the Connecticut River. It's full of interesting places to eat, drink, and shop, and it looks like the set of a wholesome Midwestern musical with a Northeastern edge.

A handful of places to go in Middletown are Harbor Park, Wesleyan University, NoRa Cupcakes, and the Parklands at Long Hill. With children, try the Kidcity Children's Museum, Adventure Rooms, and Oddfellows Playhouse.

Winsted

Population: 7,321

Winsted - an incorporated city for Connecticut's purposes but technically a part of Winchester, the larger town that almost completely surrounds it - looks like no other place in the state. Its most unusual feature, a wide Main Street with buildings lining just one side, gives this New England town a feeling of the Old West. The design is the reaction to a catastrophe. In 1955, the floods that deluged many Connecticut towns flattened much of Winsted's downtown. After that, Main Street was rebuilt to give the Mad River, which usually flows happily beside it, room to go mad again. Winsted, called the Laurel City, is one of Connecticut's earliest mill towns, and old brick factory buildings still loom large in its landscape. Now some of these mills are being put to new uses, and the city might just transform itself yet again.

Here's a selection of Winsted points of interest: the Soldiers' Monument and Memorial Park, Whiting Mills, the Gilson Cinema and Cafe, and Ralph Nader's American Museum of Tort Law.

Derby 

Population: 12,830

Derby is Connecticut's smallest city (its motto is literally "Connecticut's Smallest City") which makes it worth visiting simply as a curiosity. (How did those early settlers cram a whole city into such a small space, and why did they bother?) But although this industrious little city with a very small-town vibe is not exactly bustling with activity, there's more to this tiny municipality than a superlative. The Housatonic and Naugatuck Rivers converge here, making for some lovely waterfront walks and views. (There are also six bridges.) Preserved 19th century buildings surround Derby Green, where the road signs bear the names of female relatives of the private developers who convinced the local government to lay out the streets. And Derby is very proud of its very weird history, including this Revolutionary War story about pork.

If you go to Derby, places to check out include the Derby Greenway, the Sterling Opera House, the General David Humphreys House, and Books by the Falls. 

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.

The Other Corner

The northeast is the "Quiet Corner"; the only corner of Connecticut, as far as I know, that has a name. The southeast corner, where I live, is known for its history and casinos and longstanding ties to the sea, but in travel articles about the state, it’s often ignored. (The Neglected Corner.) The southwest corner, where I grew up, is known mainly for being near New York. (The Hedge Fund Corner, perhaps.) Recently I found myself staring at a map of the northwestern tip of the rectangle and wondering just what, exactly, was up there. I asked my Mom, who still lives in the southwest, but she had no idea either. So we set out in search of the mysteries of what I began to call "the Other Corner."

We drove north from Westport through wooded hills and big box store strip malls and road construction. A tractor supply store appeared and soon enough the suburban sameness was replaced with tiny farms and the Housatonic River began to snake slowly along beside the road. We passed a yellow Cow Crossing sign, shortly followed, comfortingly, by cows.

None of this was new. I’d been to Kent, where the sign announces that you are welcome but you kind of sense that you’re really not, and to preppy Litchfield, where people’s heads swivel around like oscillating fans when an outsider walks into a café. This wasn’t the Corner yet.

A little further north, things began to get odd, in the best possible way. A large stone chimney rose from the ground, surrounded by a circle of grass. It was only a remnant of this region’s industrial past, what’s left of the 1800’s Kent Iron Furnace, but it looked like some sort of mystical ancient monument.

We drove into West Cornwall, which has an old red-painted covered bridge. (You’d think this would be in nearby Cornwall Bridge, but you’d be wrong.) The bridge was dark inside and just wide enough for one vehicle at a time. The town was so perfect and diminutive that we cooed over it as if it was a toy town on a store shelf.

Multiple Cornwalls and numerous Canaans, all pocket-sized and adorable, overlapped in ways incomprehensible to non-locals. In Falls Village, technically another Canaan (don’t ask), the houses were elegant in a way that contemporary buildings never are, as if the town had an ordinance against extras and flourishes. We tried to explore but the gently inclining roads formed triangles which led us back to where we started. It was like they were purposely keeping us from something, vigilantly protecting what was hidden around the next turn.

The Housatonic reappeared on the other side of the road, no longer placid but flowing swiftly. The views became more expansive and the hills less thickly wooded. Now we were really in the corner of the map.

We turned east where Connecticut borders New York and Massachusetts and drove until we arrived at Haystack Mountain State Park. We drove up a one-way road, and up and up, wondering what would happen if someone came down. But no one did. When the road ended we walked, first along a soft path of dead leaves under a canopy of trees, then up an increasingly steep hill, then up stone steps two feet high. After half an hour, we were over 1,700 feet above sea level, staring up at a sturdy stone tower. A staircase curved around the inside of the cylinder; the upper level had a peaked wooden roof and a 360 degree panorama of the Berkshires. We felt thoroughly alone, but for some reason we whispered.

We drove on, intending to complete the Corner by continuing west, and then suddenly we were lost. Deeply, profoundly lost, the kind of lost you can only get in your home state on a clear day with a map on your lap. If it wasn’t all so pretty, so serene and leafy and empty, I would almost have suspected a plot. If I lived in a place like this, in one of the grand yet understated white houses that occasionally interrupted the defensive line of trees beside the road, would I want people to be able to find it?

We had been lost for so long that I couldn’t believe we hadn’t crossed a state line, when suddenly we were found. Or rather, we found something: a whole city (or in this case, a city wrapped in a town) sprang up seemingly out of the earth. Winsted, with its broad main street (widened after the devastating Great Flood of 1955 destroyed the original) looked like an Ohio River town taken apart and transported to New England to be reassembled. We passed a movie theatre, a post office, coffee shops, neat lamp-posts with banners in a row. I stared as if I’d never seen such things in my life.

We abandoned the Corner plan and zigzagged up to Riverton, which appeared to be waiting for a 4th of July parade. Flags waved proudly on both sides of the main street and the smart buildings practically begged to be draped in bunting. Even a disused factory looked distinguished. We entered the adorable white-painted General Store (really a convenience store-slash-small deli), where we looked similar enough to the other people, but heads swiveled and we could not have felt more out of place. The attitude, like the architecture, was vintage Western Connecticut: a subtle but unmistakable dismissal. We accepted their judgment, and started back.

So I’d answered some of my questions about the Other Corner, but now I had more. I wanted to learn what roads I’d been on when I was lost. I wanted to know what gave the stone structures and silent woods and deceptive roads their mysterious feeling. I wanted to figure out what was so good up there that they didn’t want me to find it.