Often I’m asked, by people who are new to Connecticut or planning to move here, “What are the places I have to see?” Obviously, anyone can turn to the Internet and instantly find a list of the state’s most popular tourist attractions. But we all know that’s not quite the same thing. And having written this blog for eleven years now, I’ve thought a lot about “official tourist Connecticut” vs. the Connecticut I love, the Connecticut I wish newcomers and visitors (and long-term residents stuck in a travel rut) could see.
So when I get that question, I have answers – too many answers, in fact, to dash off a snappy reply on the spot. And that’s why I’m writing this post. It’s my ultimate list of the seven things you must see and do to really understand and appreciate Connecticut, whether you’re visiting, living here, or something in between. These seven musts are types of activities more than particular locations, though I am including plenty of specific suggestions.
But for those who just want the quick list, I’ve also compiled my top ten Connecticut travel picks. They’re listed at the end of the post and also marked with a * throughout. These are the places I’d take someone from out of state on an ultimate Get to Know and Love Connecticut Tour.
Experience the Whole State
Despite its reputation, Connecticut is not just a bland rectangle of affluent suburbs. Sure, those exist (though they’re a lot less bland than you’d think when you really start looking.) But we also have densely populated urban areas, rural farming communities, and what the national media might call hollowed out former industrial towns. Landscapes can change in minutes from thick woods to swaths of sand and salt marsh to rolling hills. Though common characteristics tie the state’s 169 towns into a whole, it can sometimes seem like each region is a different world. And you don’t really know Connecticut until you’ve gotten a sense of them all. Luckily, it’s a small state, so this isn’t too hard! Different people and entities divide the regions up in different ways (you can search this blog for posts by region using the map here.) But to start off, these are the areas you’ll probably want to explore:
Shoreline towns. Life here is guided by the presence of the beach, by storms and sun and morning fog over the water. This is a place of seafood and sailing, summer tourist motels and slow strolls on boardwalks, and shopping for nautical-themed mementos. Take a slow drive through several towns, or pick just one or two to spend a day or more. You can’t go wrong in quintessentially coastal Stonington Borough*, Old Saybrook with its wide Main Street and scenic causeway, genteel Old Lyme, polished Guilford, or bustling Madison.
The Connecticut River Valley. The towns and cities along the state’s eponymous river still retain a sense of when this waterway was Connecticut’s link to the sea and the world. There’s just something special about the exquisite towns of Essex, Deep River, Chester, and East Haddam, and though the streets get busier as the river approaches Hartford, suburbs like Glastonbury and Wethersfield are lovely as well. The calm returns and you may spot some of the region’s distinctive tobacco sheds between the historic homes as you follow the river past the Windsors and beyond.
Fairfield County. This is the Connecticut they warned you about, the one from TV and movies and punchlines. But you’ll quickly find that this region, too, is complex. The Southern part of the county is fast-paced and crowded, but packed with some beautiful beaches, excellent shopping and dining, and a few well-preserved historic districts. Just a bit inland, visit upscale New Canaan and Ridgefield for their history and charming downtowns. Further north and west, a much calmer Fairfield County emerges, and country towns like Redding and Sherman feel almost remote, the kind of places you’ll rarely see on TV.
Litchfield County. Hilly and spacious, sophisticated and bucolic, this area is famous for fall foliage but beautiful year-round. Litchfield and New Milford have attractive, busy town centers surrounded by historic homes and beautiful open spaces. New Preston and Washington Depot are impossibly cute with distinctive little shops to match. Falls Village in Canaan and Lakeville in Salisbury are snapshots in time, the Connecticut that modernity graciously forgot. Visit one of the region’s nature preserves or state parks or drive around Lake Waramaug, stopping for stunning views, small towns, and vineyards.
The Quiet Corner. The northeastern part of the state – also called the Last Green Valley for its unspoiled nature – will draw you in with its promised quiet and win you over with lively little towns, roadside farm stands, and outdoor adventure. Walk on trails beside rivers and falls that once powered vast mill complexes and drive through fields and orchards to little towns with distinct personalities. Visit Willimantic or Putnam for artsy, quirky downtowns and sidewalk strolls. Stop in Pomfret, Woodstock, or Thompson for gently sloping farmland, centuries-old homes and schools, and storybook churches. Head to Coventry or Lebanon for stillness and Revolutionary-era history that you don’t need much imagination to envision.
Cities. All of Connecticut’s cities are steeped in history and culture. Among the larger cities (which are “large” by Connecticut standards only) Hartford* is the easiest to navigate and feels the most like a “real” big city. Historic, walkable, in turns gritty and grand, Connecticut’s capital has something for everyone, whether you like museums, parks, food, or simply being surprised by a city’s charms. New Haven has attractive neighborhoods, surprisingly rugged open spaces, and an underappreciated coastline. Bridgeport, Stamford, and Waterbury all have their own unexpected magic. The smaller cities are also very much worth visiting; try the underrated little port city of New London, where art, eclectic architecture, and restaurants abound, and you’re never far from a beach, pier, or riverfront.
Get Close to the Coast(s)
Connecticut is, quite obviously, a coastal state, and almost everyone who lives here feels a personal connection to a particular slice of the shore. Connecticut’s beaches, like everything else here, offer a good deal of variety: small or large, white sand or rocky sand, preserved wilderness or man-made convenience. Rocky Neck State Park* has a boardwalk, a long swath of gently curving sand, dramatic rock formations topped by a stone pavilion, wooded trails, and a seasonal concession building. Hammonasset Beach State Park, Connecticut’s largest beach park, has amenities that include a nature center and connects to an extensive multi-town trail network. Harkness Memorial State Park is built around a historic mansion and gardens. Almost all beaches have picnic areas, and many have campgrounds. But state-owned beaches aren’t the only ones to choose from: don’t ignore town beaches, which are free in the off-season. Some of my favorites are Waterford Beach Park in Waterford and Burying Hill Beach in Westport, both wind-swept escapes from civilization, and Stamford’s Cove Island Park, a surprising mix of green lawns, paved trails, and a wild little shore. West Haven and Milford have lengthy coastlines with many options for beachgoers. To get off the sand and out on the water, take a boat trip like this Connecticut lighthouse tour or any of the numerous options offered along the shore.
All that said, it’s important to remember is that Long Island Sound is not Connecticut’s only body of water. The state could not be what it is without its rivers, the Connecticut, the Thames, the Housatonic, and many, many more. In Essex, the Connecticut River Museum tells the story of life along that waterway, and several boat tours, like the steamboat Becky Thatcher, provide a different view of the area’s natural beauty and historic river towns. Riverside parks, like Indian Well State Park in Shelton, offer space to relax on a riverbank. And the state’s many lakes, like Candlewood, Zoar, Pocotopaug, and Waramaug – just to name a handful – are a window onto a different aspect of life by the water in Connecticut.
Explore State Parks and Forests
Like the state park beaches mentioned above, Connecticut’s inland state parks and forests are among the highlights of life in the Constitution State. Each one has something unique and rewarding to it, whether it’s untrammeled nature, history, or miles of walking and hiking trails. Camp Columbia in Morris and Haystack Mountain in Norfolk are among those where rustic stone towers await you at the top of a climb. Chatfield Hollow in Killingworth is one of several parks with a picture perfect covered bridge; it also has an elevated boardwalk trail, a pond ringed with pine trees, and a restored waterwheel. Windsor Locks Canal Trail, stretching between Windsor Locks and Suffield, is one of many linear trails, or Greenways, that repurpose a disused transportation corridor for recreation. Bluff Point in Groton is part beach, part coastal forest, part sweeping vista. Topsmead in Litchfield surrounds a postcard-perfect Tudor-style estate. A separate section of Nipmuck in Union is a dedicated Mountain Laurel Sanctuary. Nachaug in Eastford contains the remains of the home of the first Union general to die in the Civil War. Nehantic in Lyme and East Lyme, and Peoples and American Legion in Barkhamsted, are perfect places to go when you want to feel isolated and small in a world of trees.
Embrace Local History
In New England, the past is unavoidable: our towns are old, our houses are old, and sometimes it seems you can barely cross the street without encountering a building where George Washington once slept. So while you’re in Connecticut, you might as well get into that history and seek out some particularly significant sites. Fortunately, our historic places are among the prettiest and most interesting in the country.
The most ubiquitous aspect of Connecticut’s history is its well-preserved houses and public buildings. To admire the best collections of these, walk around one of Connecticut’s historic districts, which often cluster around attractive town centers. Some of the best, biggest, and easiest to explore are in Old Wethersfield, on Main Street and around Broad Street Green; in Fairfield, between the Old Town Hall and the beaches; in Glastonbury, on Main Street in the town center and extending south; in Litchfield, surrounding the town green; and in Madison, around the town center on Route 1.
It doesn’t get much more New England than a classic town green, and Connecticut has a whole lot of them. The Guilford Green* is arguably the prettiest. This large, park-like square is edged with lovely shops and eateries and surrounded by blocks of historic homes, most notably the Henry Whitfield House, the oldest house in Connecticut and the oldest stone house in New England. Milford and New Milford also have beautiful, large greens surrounded by vibrant downtown areas. New Haven and Waterbury are good examples of greens that retain their central place despite finding themselves in modern, urban settings.To get the best sense of how the original towns greens functioned as common grazing land, head to Lebanon, where the mile-long green is more like a meadow than a manicured lawn.
On Lebanon Green and in the house museums surrounding it, tales of Washington and Rochambeau come to life. The Revolution impacted many towns in what was then nicknamed the Provisions State, and those stories are recalled at striking historic sites like Fort Griswold State Park* in Groton and Putnam Memorial State Park in Redding.
But Connecticut history isn’t just Colonial history. Erstwhile industrial pursuits have left fascinating remnants of the past in old mill towns like Putnam, Willimantic, and Plainfield; curious attractions like Mine Hill Preserve in Roxbury, the Beckley Furnace Industrial Monument in North Canaan, and the Old New-Gate Prison and Copper Mine in East Granby; and abandoned places turned public spaces like Gay City State Park in Hebron.
And of course, Connecticut’s population being as diverse as its topography, there’s also substantial African American history (the Connecticut Freedom Trail documents and catalogues significant sites), Native American history (several museums and many dozens of informational markers and plaques around the state – as well as endless place names – tell these stories), Jewish history (drive through rural Connecticut and you may spot a diminutive early 20th-century synagogue), and many more sites honoring the histories of the many groups who made, and still make, Connecticut such a fascinating place.
Go on a Road Trip
Too many people get their only impression of Connecticut from the highway; it’s no wonder they think of the state as an indistinct blur of trees, billboards, and office towers between Point A and Point B. But get off those highways, and whole new worlds appear. Because Connecticut is so compact, just an hour of driving on local roads can take you through cities, suburbs, and small towns; between hulking brick textile mills and beneath canopies of leafy trees; and past historic churches, houses, and cemeteries. On any one drive, you can spot dozens of things you would never have guessed were there.
Follow Connecticut State Route 169*, a 47-mile National Scenic Byway that runs from Norwich to Woodstock through the small towns and farms of the Quiet Corner. Or drive north on Route 7 out of busy Fairfield County into Litchfield County, where upscale meets rustic and winding roads lead to covered bridges. Or drive up the Lower Connecticut River Valley*, crossing the water on tiny car ferries or historic bridges, stopping in pretty river towns and taking in the natural beauty of the region. Or just tell your GPS to avoid highways, and find your own back road adventures.
Eat Some Signature Connecticut Foods
Connecticut is known for what probably sounds to outsiders like an odd selection of menu items. (To be honest, a lot of them sound quite odd to me too.) Local specialties include lobster rolls (hot not cold, butter not mayo); seafood shacks generally (any waterfront town will have at least one); and steamed cheeseburgers. Being an inventive place in general (Connecticut brought you the frisbee, the submarine, the cotton gin, and the toothpaste tube – you’re welcome) it’s not surprising the Nutmeg State has dreamed up some new foods, too, like lollipops and hamburgers, both of which were born in New Haven.
But Connecticut also produces some of my ultimate favorites. New Haven Pizza* (Neapolitan-style, thin crust, charred, you’ll see it called Apizza) is, to this native Manhattanite, far superior to New York or Chicago-style pizza. (I love a simple red pie from Bar, but Sally’s, Frank Pepe’s, and Modern are the most popular choices.) There’s nothing like homemade black raspberry chocolate chip frozen yogurt from a rural ice cream stand* like Rich Farms in Oxford, Buttonwood Farm in Griswold (where the above photo was taken), or Salem Valley Farms in Salem. And though the foods themselves aren’t specific to Connecticut, there’s something extra special about locally grown produce and wine from Connecticut vineyards. (My favorite is Saltwater Farm Vineyard in Stonington.)
Celebrate the Season (and the Off-Season)
In Connecticut, people live for the seasons, and the seasons shape people’s lives as few other factors do. Perhaps because each one can feel so long and bring so many hardships – hurricanes, Nor’easters, blizzards, floods – we celebrate the changes and the events each season brings. Summer equals beach time, ice cream stands, seafood shacks, sidewalk tables, picnics on the grass or the sand, farm stores, farmers markets, and agricultural fairs. Fall means hot apple cider, warm apple cider donuts, buckets of apples at farm stands, pumpkins everywhere, and garden centers full of multi-hued mums and seasonal gifts. Winter is for admiring the twinkling lights and decorations that pop up along almost every Main Street, drinking hot drinks in cozy coffee shops, and bundling up to experience the beauty of freshly fallen snow, rivers turned to roads of ice, and forests turned sparkling wonderlands. Spring is about flowers: daffodil festivals, cherry blossoms, and blooming gardens in municipal parks.
But to really get a feel for Connecticut life, you have to appreciate the off-season too. That means walking on the beach in fall and winter, when the tourists are long gone; wandering inland woods and city streets in summer, when everyone else has flocked to the coast; and taking advantage of those otherwise inconvenient spring rainstorms to see the state’s numerous waterfalls in full force. (I like Yantic Falls in Norwich, Case Falls in Manchester, and Chapman Falls in Devil’s Hopyard State Park, but there are many others.)
My Connecticut Top 10
1 Stroll through Stonington Borough.
2 Explore Downtown Hartford.
3 Have a beach day (whatever the season) at Rocky Neck State Park in Niantic.
4 Be charmed by historic Connecticut on and around Guilford Green.
5 Be awed by historic Connecticut at Fort Griswold Battlefield State Park in Groton.
6 Get to know the Quiet Corner along National Scenic Byway Route 169.
8 Find the sweetest small river towns on a Connecticut River Valley road trip.
9 Eat some New Haven Pizza.
10 Enjoy some local ice cream (or another frozen dessert) at a rural ice cream stand.