Fairfield County is the most densely populated area of Connecticut, and the richest. Often called the “Gold Coast” or the “bedroom of New York,” this is one of the most exclusive counties in the entire nation. Named for its most prosperous colonial town, the county now boasts a string of cities along the Old Post Road and a hilly interior of prosperous suburbs. Though swamped with wealth, the county surprisingly retains much of its charming character, and we can thank our fussy Yankee values for not allowing it to become a haven of ostentatious excess.
The exclusive addresses of Greenwich, New Canaan, Darien, and Westport give the county its reputation, filled with celebrities and entrepreneurs who have settled here for a quick commute to New York City. Greenwich boasts some of the best restaurants in the county and the finest stores in the world. Darien has been a retreat for New Yorkers since the Civil War and Westport has been called Beverly Hills East.
Anchoring these communities is Stamford, a large city that has recently become a vital center of corporate business, with its motto “The City that Works.” The city of Norwalk has also been revitalized, with the restaurant district of SoNo, which jumps with small bistros, galleries, and shops, and an arty, grit-and-polish feel and WPA murals.
Further up the coast, Bridgeport has not experienced the revivification that Norwalk and Stamford have, but boasts some of the county’s biggest attractions, including Fairfield County’s largest music and sports venue, Bluefish Stadium and the Arena at Harbor Yard. A hundred years ago this was the richest and most powerful city between Boston and New York, and vestiges of its former glory linger in its parks and downtown, and along some of the tree-lined avenues. Surrounding Bridgeport are Stratford and Fairfield, two colonial towns that have risen again to prominence. The nexus of universities in the area recently earned it a nod from the American Institute for Economic Research as one of the best college “metro areas” in the nation.
The interior of the county is mostly a string of wealthy suburbs: Wilton, Weston, Easton, and Trumbull. Unlike tract-housing suburbs in some other areas of the country, however, they are heavily forested, and feature diverse homes. The former “hat city” of Danbury is the western gateway to the state, benefiting from the influx of wealth as the New York metro area expands. And the charming towns of Ridgefield, Newtown, Redding, and Bethel grant a quaint, clapboard feel that everyone expects of Connecticut.
Fairfield County contains amazing attractions, from wildlife encounters to historical homes. If you are a foodie, this is heaven, full of fascinating restaurants, from the fanciest French gourmets to the yummiest hot dog joints. And the shopping is by far the glitziest and most glamorous in the state. Keep an open mind and an open wallet as you explore this gateway to the pleasures of Connecticut.
Mark Twain said once of Hartford, “Of all the beautiful towns it has been my fortune to see, this is the chief . . . You do not know what beauty is if you have not been here.” Sure, he might have been talking about the city when it had the highest per capita income in the US. But there are beauties to be found here still, and the surrounding suburbs and villages have some of the most interesting attractions in the state. Hartford County surprisingly includes the most remote area of the state, on the Tunxis Trail, while the tobacco farms that fill the rich, flat floodplains around the Connecticut River seem out of place in central New England.
The history is long and rich here, and in general, more relics and houses have been preserved, possibly because this is the state capital. Hartford is widely known as the insurance capital of America, though it was once known for its revolvers. Like the best cities, Hartford rings a large public park, Bushnell, the oldest in the nation. The Hartford Courant is the nation’s oldest and longest-running newspaper, and the city also contains the oldest art museum, the Wadsworth Atheneum.
The county also boasts the oldest continuously operating ferry in the US, crossing from Glastonbury to Rocky Hill; the state’s oldest settlement from 1633, Windsor; and its oldest gravestone, Rev. Ephraim Huit’s, 1644. Old Wethersfield is only a year younger than Windsor, and its collection of 17th- and 18th-century houses is unrivalled. But Hartford County also looks to the future, and Windsor Locks has the state’s only international airport, Bradley.
The larger suburbs are really cities themselves, including Manchester and West Hartford, both great places to shop and eat. At the south end of the county, Bristol and New Britain are old industrial cities that now contain art and history museums, as well as large companies like ESPN. The New England National Scenic Trail heads along the traprock ridges that form the spine of this county, and you can step out of these cities into a seeming wilderness in minutes.
To the west are the charming towns of Simsbury, Burlington, Canton, and Granby, retreats and homes for the city’s elite. The Farmington is the best-stocked trout river in the state, and its long, tumbling length is haunted by anglers, as well as kayaks, canoes, and rafts in the summer.
You’ll find very quickly that Hartford is more than just the state capital. Take your children to the country’s longest-running amusement park, or take yourselves to a romantic dinner on the breezy porch of a country inn. Whatever you do, take your time to explore the diverse attractions of this county on your travels through Connecticut.
Often called the playground of Connecticut, New London County’s population is a third of New Haven, Hartford, or Fairfield Counties’, but it brings in over a third of the state’s tourism. The two Native American gaming casinos, Foxwoods and Mohegan Sun, have become two of the biggest destinations in New England, and with the maritime activities, the wineries, and the well-preserved historical attractions, this area of the state is simply too good for you to pass up. You could easily spend a week seeing everything here without venturing into any other part of Connecticut (not that you should).
Mystic was a destination long before Humphrey Bogart and Lauren Bacall honeymooned here. The historic seaport and the aquarium anchor a tourist town steeped in maritime history, and nearby Stonington has a beautifully preserved village for those who aren’t as interested in shopping and restaurants. The harbor of New London is a home of American sea power, with Fort Trumbull, the Coast Guard Academy, and the Nautilus submarine all big draws. At the west end of the coast, the towns of Lyme and Old Lyme have maintained their rural charm, and the Florence Griswold House was the center of American Impressionism.
The entire seashore surrounding these towns is dotted with parks like Rocky Neck, Harkness Memorial, and Bluff Point, giving the visitor an opportunity to explore wooded beaches that the Native Americans used centuries ago. You can charter cruises on the Sound from almost any of these seaside ports to fish, learn, or party.
Inland, the city of Norwich and its environs boast the two casinos that bring thousands of people from New York and Boston every day. They are not just coming for the gaming; these are two of the largest and most beautiful casinos in the entire world, featuring shopping, restaurants, and events like concerts. The nearby Mashantucket Pequot Museum has been called the best museum of Native American history in the country, competing only with the Smithsonian. Walking through a completely reconstructed Pequot village makes you almost not mind losing at the Foxwoods gaming tables that evening.
And though it seems so far north that it should be part of a different county, Lebanon is a must-see for anyone interested in American history. The town green and surrounding houses are among the most important sites of the Revolutionary War.
In short, New London County is the place to be. Although most of these attractions are geared toward the summer visitor, you will find something to do here in any season. And whatever you do, don’t forget to bring your appetite for the local Noank oysters and littleneck clams. They are as delicious as they were when the Pequots treasured them centuries ago.
The Connecticut River was at the heart of what was once the Old Saybrook Colony, and it remains so today. Poet Wallace Stevens called it “the river of rivers” and said: “It is the third commonness with light and air, a curriculum, a vigor, a local abstraction. Call it, one more, a river, an unnamed flowing, space-filled, reflecting the seasons, the folk-lore of each of the senses; call it, again and again, the river that flows nowhere, like a sea.” The mouth of the Connecticut by Old Saybrook was recently called one of the 40 last great places in the Western Hemisphere by the Nature Conservancy.
The smallest Connecticut county geographically, Middlesex is also generally flatter than the others, though it contains many small rocky hollows and rises up from the river and the coast in rolling hills. Until recently, travel was primarily by boat, and today there are still only three car bridges that cross the wide river in the whole county, at Middletown, East Haddam, and the I-95 bridge at Old Saybrook.
Old Saybrook itself is a charming town that for most of the 20th century was the home of Katharine Hepburn, winner of more Academy Awards than any other actor. She started her acting career up the road at the famous Ivoryton Playhouse. The other two coastal towns of Clinton and Westbrook have become famous for their shopping outlets and their charming resorts.
Ivoryton got its name from the business of making piano keys, and today forms a nexus of charming villages with its neighbors of Essex, Deep River, and Chester. Essex is often cited as one of the prettiest towns in the nation, and that distinction is difficult to argue with. All these towns along the western side of the river have great antiquing. Across the river, Gillette Castle in East Haddam is another huge appeal for visitors to the state, and all these attractions make this part of the river a popular place to canoe and sail.
The north end of the county is anchored by Middletown, where Wesleyan University sits high on a hill, bringing culture and wealth to the area. This is where, long ago, the Connecticut River’s course may have changed, from heading directly south to modern-day New Haven, to its present southeasterly course. Whether or why it did so remains a mystery—one of many that you will find to intrigue you in Middlesex County.
The old New Haven Colony nearly became the center of Connecticut, and shared the capital with Hartford for many years. The colony’s harboring of three rebel judges from England was probably the only thing that prevented it from becoming its own state. But New Haven became truly its own city and cultural area with the founding of Yale University, which for the last 300 years has brought the area refinement and wealth.
The center of the county in many ways, New Haven is Connecticut’s second largest city after Bridgeport, and is chock-full of museums, theaters, and exciting annual events. Few would argue that Fairfield County as a whole might have better restaurants, but no single city has as many top-quality (and famous) eating establishments as New Haven has. This was the oldest planned city in America, and you can still walk the old green and among the towering spires of Yale, imagining the fight against the British here in the Revolutionary War.
The immediate suburbs of New Haven—Hamden, East Haven, and North Haven—all have their own characteristics. Though this is the third most populous county in the state, hiking and biking trails abound, like the Quinnipiac Trail, the oldest in the state’s extensive blue-blazed system, in addition to huge parks like Sleeping Giant, and the Farmington Canal Greenway.
New Haven County also contains a number of towns along the shoreline of Long Island Sound. To the west, Milford and West Haven are more-populated suburban towns with fine beaches and parks. To the east, Branford, Guilford, and Madison have quaint village centers along the Old Post Road that hearken back to times gone by.
At the north end of the county, the factory towns Meriden and Waterbury are still huge population centers. Waterbury has some fine museums, and Meriden features the wonderful vistas of Castle Craig in Hubbard Park. South of Waterbury are the old industrial towns of the Naugatuck Valley, designated an “All-American Valley” for its part in the textile and brass industries. Meriden’s suburb of Wallingford is a charming town built around one of the best private schools in the country, Choate Rosemary Hall.
In between these larger towns are quiet rural communities like Oxford, Bethany, Prospect, and North Branford. But New Haven County’s charms are not like Litchfield’s or Windham’s. This county is a healthy mixture of town and gown, seaside and mountain. With restaurants rivaling Fairfield County, and attractions rivaling New London, this area has a little of everything for all tastes and inclinations.
Tolland County takes great pride in being the home to Nathan Hale, American patriot, spy, and martyr of the Revolutionary War. In the sleepy town of Coventry you can find his homestead and memorial, engraved with those immortal words, “I only regret that I have but one life to lose for my country.”
The county’s social life revolves around Storrs, the home of the former agricultural land grant college that became the University of Connecticut. UConn causes the county’s population to jump by over 20,000 every September, and stay that way until May. Famous for their championship Huskies basketball teams and for being the top public university in New England, UConn is beloved by people throughout the state who haven’t even gone there for school. Storrs itself is a classic college town, simply crawling with Husky fever.
North of I-84 is Stafford Springs, home to one of Connecticut’s premier car-racing venues, Stafford Motor Speedway. Otherwise, the north half of the county is full of sleepy towns that are excellent places to find a little peace and quiet. Tolland itself has been rated one of the best towns in the country to live in.
Tolland may be the smallest Connecticut county, but it is full of both national and local pride. Visiting here will surely instill you with it, too.
What is home? This is a question that often troubles our nomadic society. Home is certainly more than the place we lay our head to sleep each night, or labor at in the day. Maybe it is a feeling, a spirit, a state of being. We might even think it is just an illusion. Whatever it is, we search for it, traveling the gray back roads of the world, wondering what we are missing. In the words of native son and playwright Eugene O’Neill: “Obsessed by a fairy tale, we spend our lives searching for a magic door and a lost kingdom of peace.”
There are many places in this world that promise you that fairy tale, easy to imagine and in reality hard to live with. Connecticut is a doorway to the truth.
Here you can walk through some of the oldest buildings in America, and feel moss on the stone walls of colonial farmers. You can taste a fried oyster in a seaside restaurant or the first sip of this year’s Chardonnay in a local vineyard. You can fish the small, stony rivers or hike the edge of traprock ridges. The loamy smell of deep forests might call, or the salty tang of long golden beaches.
One thing becomes abundantly clear: There is no one path to knowing the truth Connecticut offers. You may find it on the green grass of a hill, on the porch of a clapboard inn, or at the top of a roller coaster. It is waiting for you at a farm stand, at an antiques store, and at the curve of the next country road. You can find truth through our paintings, our architecture, and our music. And hopefully you will find it in the people you meet, in their sparkling eyes and firm handshakes.
Literary giant Wallace Stevens once said, “There is nothing that gives the feel of Connecticut like coming home to it.” He found that feeling in the ground beneath his feet each day on the way to work. “Going back to Connecticut is a return to an origin . . . an origin of hardihood, good faith and good will.” Long before Stevens composed poems on the streets of the state capital, the ardent patriot of the American Revolution, Nathan Hale, found his own truth here before the United States of America officially existed. He loved Connecticut so much that he died for it, sneaking into British-controlled New York City, not in the pursuit of some abstract freedom, but to save the home he loved. “Home”—Hale understood what that word meant, and though he died before he could tell us more in words, his actions speak to us over two centuries later.
Connecticut offers visitors and residents alike glimpses of that unspoken truth. What is it, you ask? I can only tell you what I found in the years since I made my home here, something that Nathan Hale might have echoed had he lived. We must first become patriots of a small plot of earth, then a watershed, then a township, a county, a state. We must love, and love deeply, the people around us and the earth we stand on. Only then can we be in the real and truest sense patriots of a nation, and hopefully of the human race.
Is that what you will learn here in Connecticut? It’s time to find out.
When people think of the charming country life of Connecticut, they are usually thinking of Litchfield County. Forested hills and dales punctuated by idyllic farms and delightful villages make up most of this area. Bounded by Route 84 on the south and Route 8 on the east, the Litchfield Hills have called people from the nearby cities for over a century. At one time this area was a hot spot for logging and mining, but no longer. Tourism is the county’s main business today, despite some small population centers in Torrington, New Milford, and the northern suburbs of Waterbury. For visitors seeking beauty of both land and culture, search no further.
Woodbury and Kent are antiquers’ dreams, and a great introduction to the joys of shopping without the pressure or prices of the bigger cities to the south. Litchfield itself is a charming hill town; its town green has shops and restaurants along one side and the state’s most photographed Congregational church on the other. Due to its accessibility off of Route 8, it can be the busiest of the county’s towns on a weekend morning, but you simply can’t miss it. Nearby Bantam and Goshen are “blink-and-you-missed-it” small towns, but have hidden rewards if you know where to look. In the far northwest corner, Sharon, Lakeville, and Salisbury are so far away from metropolitan centers that sometimes it seems they have remained in another, older and slower time. That is, until the cars at Lime Rock’s NASCAR track speed things up on summer weekends.
Roxbury was once home to sculptor Alexander Calder and playwright Arthur Miller, and has more famous residents today. Don’t expect the residents to point the way to their houses, though; privacy is considered a cardinal virtue in New England. Towns like Washington, New Preston, and Cornwall hide their own treasures, with charming bookstores and covered bridges, wineries and waterfalls. You’ll need an insider, or at least an insiders’ guide, to find them.
The Housatonic River is a fly-fishing paradise, and the white blazes of the Appalachian Trail guide thousands of hikers through the county every summer. In the autumn, this is one of the best leaf-peeping areas in the entire world, and the many inns and B&Bs can be booked months in advance. However, Connecticut is so easily accessed that a day’s drive in the Hills is no problem from any of the nearby counties. Drive or walk through displays of red and yellow and orange that you’ve only seen in photographs.
Norfolk, Canaan, Goshen, Riverton . . . the list of charming towns with country inns waiting for you to relax on their porches can seem endless. But time itself doesn’t seem to move slower in Litchfield County, it actually does move slower. Visit and find out how they do it.
Windham County is sometimes known as the “Quiet Corner” of Connecticut, and it certainly is quieter than most, with the lowest population and position farthest away from the major cities of the surrounding states. It also forms the center of a National Heritage Corridor, the Last Green Valley, a natural and cultural area more than 78 percent forest and farmland with thousands of historic buildings.
Windham is anchored at two ends by the slightly larger settlements of Putnam, a former mill town, and Willimantic, the “Thread City.” The rest of the county is made up of small villages like Woodstock, Pomfret, Brooklyn, and Scotland, where beautiful country roads take you to antiques shops, historic homes, and bed-and-breakfasts. Camping, hiking, and fishing opportunities are plentiful out here, and the numerous farms offer agricultural tourism and tasty rest stops.
When flying at night from Washington, DC, to Boston, you can look out the plane window and see an unbroken stretch of light from the megalopolis of cities and suburbs. All except right here, in Windham County, the heart of the last green valley.