Holidays in Connecticut? Anyone who has visited New York finds it hard to imagine a lifestyle so completely different just two hours away (by train or car) from the city.
In what is known as Litchfield County, in a part of northwestern Connecticut, the quality of life is incredible. Everything is so peaceful, green, and quiet. Local farms offer organic produce, there is virtually no crime, and the community and volunteers play a major role. You can find art, design, and beauty everywhere. Perhaps it’s true that when life is good, everything feels easier?
During and after the pandemic, many fled the Big Apple to move to the countryside. Some continue to work remotely, others prefer to take the train every day to commute to their offices in New York, while others escape to the countryside the moment the weekend arrives. Here is everything I observed and felt about life in this part of America.
Located in the northeastern United States, New England- which includes Maine, New Hampshire, Vermont, Massachusetts, Rhode Island, and Connecticut - is a delightful mix of natural beauty, history, and vibrant culture, offering experiences for every traveler.
One can’t help but wonder what the English pilgrims felt when they first spotted this land, after months of transatlantic navigation, back in the 17th century. And think also of the Native Americans, the Indigenous peoples, who lived here in harmony with nature and relied on hunting, fishing, and agriculture, preserving a culture rich in traditions. Not many know that even today, the day after Thanksgiving is Native American Heritage Day (November 24), which remembers the genocide of the local population.
The region I am going to tell you about is a part of Connecticut (the Constitution State—as you can read on the car registration plates—or the Nutmeg State), which falls squarely into what has been dubbed "America’s Gold Coast".
The Fairfield area, north of New York, is undoubtedly much more expensive and exclusive, while Litchfield County is a more open and natural province, with rivers and parks. Quite a different thing from the capital, Hartford, which is one of the poorest cities and completely different from the others.
Renting a car is vital for all travel. Every family almost always has a pick-up truck and another vehicle to get around. There is no public transport and everything is at least 30 to 40 minutes away, even just for a grocery run.
I took the train from Grand Central Terminal in New York to visit some friends, and it stops at tiny stations in the middle of nowhere—you won’t even find a taxi, just plenty of green space and silence. If this old train, which takes two hours, were replaced by a faster one, you would certainly find more commuters and it would start to get more chaotic here too.
Companies like Hertz allow you to rent a car and do a drop-off in a different city for your road trip. Online you can choose the vehicle you prefer and check the insurance options included in your contract. Usually, these are pick-up trucks or super comfortable cars with heated seats and a large display that connects to your phone to make traveling easier with Google Maps, make a call, or receive a WhatsApp message.
On the windscreen near the rearview mirror, you will definitely find the E-ZPass. If you leave this little box open, the tolls are automatically charged to your credit card, so there is no need to pay in cash.
Sitting in these powerful cars and following the road signs can cause a bit of tension at first, especially if it’s your first time, but if you drive cautiously everything will go smoothly. Just remember that in America you can overtake on both the right and the left, and alcohol is absolutely not tolerated. Throughout the trip, I never saw anyone exceed the speed limit. The police often go unnoticed, but they are always around the corner.
Staying in this part of Connecticut is certainly easier than it used to be, I am told. Before, the small hotels—the Inns—were bought and transformed into private homes because they produced less value than the real estate itself, so people preferred to live in them.
Today, however, things have changed. Thanks to Airbnb you can find accommodation, alongside hotels with rooms that can cost $600 a night, or $900 at weekends. There are also those who prefer the wild style of camping in state parks, but you need great equipment for nights under the stars, which shine as clear and bright here as in the desert.
Having the opportunity to stay in Litchfield County with friends and observe the local habits so closely was a wonderful gift for me. In August, the weather in Connecticut is beautiful. The temperature is perfect and in the evening you always need a jumper, just like indoors since the air conditioning is always set very low (the only downside, but it’s like that everywhere in America).
It’s hard to imagine these villages covered in snow. Yet the winter temperatures in these areas are so harsh that they push many retirees to move, with very little, to Florida or Arizona, even populating entire condominium complexes. If it weren't for the harsh winters during certain periods, life in these areas flows peacefully and without too many surprises: you have privacy, plenty of green spaces, no traffic, and charming little shops that close at five in the afternoon. Connecticut is right for you if you love this dimension.
Among the 50 US states, Connecticut ranks 48th in total land area, but it is one of the most densely populated. Yet, if you live in Litchfield County, you might not realize it for the rest of your life. The taxes, however, you feel them all, because they are among the most expensive in America (not on the house, but on earnings).
In Litchfield County, nothing is built without strict regulation. Some land belongs to the State, while other areas are purchased through fundraising initiatives and preserved by non-profit organizations, the Land Trusts, like the one in Steep Rock . Federal regulation supports this process, encouraging donations and reducing taxes. This is why those with a lot of money in America invest hundreds of millions of dollars in these charitable activities.
The great sense of community among the inhabitants of the villages—those who are part of small, often very small realities—is the true core of life in this part of the world. I notice it from the charity events I come across, from the organization of benefit initiatives, and from the stories of my friends, and it is by no means something to take for granted.
Even if they do or have done something else in life, many sign up as volunteers, such as firefighters and emergency personnel. So if needed, they are the first people to arrive at your home, also because the nearest hospital is often no less than 30 minutes away. Incredible, isn’t it? Not to mention that the state grants tax breaks to those who volunteer and support charitable causes.
Amidst so much greenery, I honestly didn't expect to stumble upon some of the most prestigious schools in America for over a century, like the Kent School or Hotchkiss.
Originally founded by Episcopal orders, they still practice self-reliance today: students are expected to work as well as study. A path that proves fundamental in helping to shape the individual's character - intellectually, socially, ethically, and spiritually- to make a difference in the world. This is why they are called "Preparatory Schools".
At these levels, education is an incredible business that attracts students from all over the United States, as well as from other parts of the world. Naturally, it requires money; it starts from $60,000 a year per student, though this varies depending on family income. Despite the exclusivity that has always distinguished these schools, known for their high level of preparation and strict selectivity, scholarships are always made available.
Sport is another important aspect, with golf, American football, lacrosse (an ancient sport invented by Native Americans), ice hockey, and tennis practiced daily, featuring tournaments that ignite competition with other schools, which remain open until June and resume in September. For a teacher, having a three-month summer break can be a great prospect, considering that the average American worker gets only two weeks of holiday a year.
What affects the quality of life is certainly also the lack of crime and the widespread affluence. In Connecticut, there is very little police presence, precisely because there is so little crime.
Most houses are still left unlocked. Things, I am told, probably began to change with the pandemic, when many fled the city and started getting used to deadbolts, security cameras, and alarms just like in New York.
Another thing that surprised me is that the houses have no curtains or shutters. I knew they weren’t common, but I hadn’t imagined the life of those who can wander around freely without finding indiscreet eyes peering through their windows. So you can take a relaxing shower while looking at the countryside, with light filtering in everywhere, at least in summer, since every room has numerous windows.
Privacy is also guaranteed by the fact that in America everything comes in an XXL format: the gardens surrounding the houses, or rather beautiful country homes, are ultimately acres and acres of green land, where in the morning, if you are lucky, you can spot deer or a black bear having breakfast with the apples from your tree.
A healthy lifestyle is best appreciated at the dinner table. If we are used to thinking of America as one big cheeseburger, this region of Connecticut will make you think again.
Local farms here focus heavily on organic, non-GMO produce. It might shock some to learn that a few kilos of organic vegetables can actually cost more than a beautifully aged steak, but that’s America for you!
Everything premium is sold at high prices and displayed impeccably. When shopping, just remember to read the labels carefully, especially because you’ll spot plenty of "Italian" products like ravioli, Sorrento lemons, and the famous meatballs, which actually have very little to do with genuine Italian food.
On these farms, you can find sweetcorn - local and absolutely delicious - but also turnips, fresh eggs, and many mouth-watering products that can end up on the outdoor barbecue on the very same day. When shopping, just remember to read the labels carefully, especially because you’ll spot plenty of putatively "Italian" products like ravioli, Sorrento lemons, and the famous meatballs, which actually have very little to do with genuine Italian food.
Aside from the farm shops, if you drive carefully, along the road you can spot signs advertising the sale of onions, cut flowers, vegetables, and much more. You will be surprised to learn that there are no shop assistants waiting for you. You simply choose what you want, note down your purchase with a pen and paper provided, leave your cash, and take your own change. It runs entirely on the honour system.
In this part of Connecticut, even a humble flowerbed in the middle of a driveway is adopted and ends up green and blooming, more beautiful than before. It is difficult to determine where my property ends and yours begins, not because it isn’t clear what the boundaries are between what is mine and what is yours, but because there is great care for everything else, which ends up becoming one big shared garden in the most metaphorical sense of the word.
I believe it is more or less the same for art, at least that is my impression. Through a sort of osmosis, everything beautiful and creative in a space ends up contaminating everything else. Not only is there a reverence for beauty, but also a desire to share culture, whether it’s music or contemporary art. These activities do not seem born to make a profit, but to entertain, surprise, and delight, I imagine.
Thus, a tiny dot in the middle of the greenery becomes an independent craft distillery with a fancy food truck, while in an old farm, a silo transforms into the futuristic interior of what looks like a spaceship bound for the moon. Meanwhile, driving for miles in your car, you can stumble across a space dedicated to design and antiques where Renaissance treasures sit comfortably alongside contemporary art.
This distillery was established only in 2021, but it is a hidden gem that has already been discovered by The New York Times, which dedicated an article to it. Tenmile Distillery was founded in Wassaic, New York, with the intent of creating a small independent distillery to return to traditional whiskey-making methods.
“At Tenmile,” their website reads, “there are no frantic production schedules. Our goal is to produce best-in-class spirits, with the best ingredients, with the best professionals, so we take our time.” In short, it seems like the perfect project that aligns beautifully with the rhythm of life in this part of America.
The estate is a dream. You are welcomed by fragrant herb gardens at the entrance, and the interiors are housed within the wide, bright spaces of an old barn. All around, acres of lawn stretch as far as the eye can see, dotted with fruit trees. The deep silence is broken only occasionally by the whistle of a passing train.
The food truck is super cool and shines in the sunlight; you can eat outdoors, order a cocktail at the bar, and taste a menu of delicious yet delightfully simple dishes.
At RT Facts in Kent, you can easily lose hours browsing through eclectic garden ornaments and the most extraordinary curiosities, each meticulously catalogued and boasting its own history.
The space possesses an undeniable soul and personality, a direct reflection of its founders, Greg and Nathalie Randall—a couple who complement each other beautifully in both life and business. Their decision to leave New York City for Kent back in 1992 was incredibly visionary. This area, once considered far removed from the futuristic glamour of the city, is now a magnet for celebrities looking to style the country retreats they escape to for peace.
You don’t just come here to buy an object; you come to take home a piece of history and enjoy a proper chat with two people who feel like old friends by the time you leave. Their highly curated taste spans across vastly different eras, satisfying the whims of even the most discerning clients.
Top-tier interior designers and architects regularly compete to style Connecticut’s grandest residences using their stock. Indeed, it is quite common to spot pieces designed by Greg and Nathalie gracing local estates or published in major international design magazines—coveted by industry professionals who inevitably return here time and time again.
My journey comes to a temporary close at Spring Hill Gathering. I had a suspicion this wasn't the work of ordinary people, and looking into the background of the founders who launched the project in 2017 proved me right.
Stephanie and Tim Ingrassia possess professional CVs that would make anyone blush. They are highly successful individuals operating at the upper echelons of America's cultural and financial sectors. Yet, they deserve immense credit for investing their own wealth into transforming an 18th-century farm, nestled in a dense woodland clearing, into a cultural sanctuary for the local community.
The estate features a breathtaking amphitheatre sculpted by artist Mark Mennin, while the old barn serves as a natural stage for open-air performances and rotating art exhibitions showcasing works worth thousands of dollars. Even the public loos, designed by artist Randy Polumbo, occupy a beautifully repurposed vintage train carriage, threatening to steal the show from the main exhibits.
What struck me most is how extraordinarily welcoming the entire space is. Beyond the food truck and the option to taste their home-produced wines, the lawns are dotted with complimentary garden games and picnic benches, open to families, children, couples, and anyone else who wishes to wander into Spring Hill.
So... will you be making your way to this special corner of America?