This East Coast Destination Is an Autumn Lover’s Dream—With Apple Orchards, Elegant Inns, and Forest Hikes

Thirty years ago, my husband, Mark, and I began looking for a weekend house outside of Manhattan. He is a sculptor who carves stone, mostly granite. His pieces were getting more monumental, and he had just started work on a large commission for what would become New York City’s Chelsea Market. Even if he could have afforded a studio in the city, no urban warehouse could accommodate the growing scale of his sculptures and the heavy machinery required to create and transport them. I was a television producer and had just given birth to our first baby, Ray, so I was bushwhacking through the badlands between motherhood and a 24/7 career. 

Our New York City home was a 600-square-foot apartment, where Mark and I pulled down a Murphy bed each night while Ray slept in the tiny bedroom he would soon share with his sister, Ava. We had fantasies of life in the country: the kids chasing fireflies on summer evenings, or clearing a patch of dirt where they could plant pumpkins and daisies. With a secondhand Volvo full of optimism, and all of $20,000 to spend on a down payment, we set out each weekend from New York with Ray in his car seat. Sixty-six viewings later, we threw our meager savings into a hulking wreck of an unfinished house just two hours away in northwestern Connecticut, in Litchfield County, with enough land for Mark and his tons of stone to spread out. 

Had I known then that, within six years, we would close the door on our city life and relocate here for good, I might have chosen a town that had sidewalks, maybe even a handful of streetlights, or a train to the city (the nearest station is an hour away). Then again, I had not yet learned that in this enchanted corner of New England, remoteness is kind of the point. 

The adjustment, at first, was drastic. The first autumn came on fast. October winds swayed my car, where I spent hours each day—15 minutes driving my kids to school, 15 to piano lessons, 15 to the grocery store, 30 if I wanted fresh Parmesan cheese. I missed street life, public transportation, even sirens. One day, as I was heading home at twilight, I didn’t pass a single car on the road, only an amber-colored fox slipping into a cornfield. 

But inevitably, the glowing images of my 20-year history in New York (and Paris before that), and my heartache for city life, began to fade. In time, I came to understand that by landing in Litchfield County, we did not simply move to the country. We found our way home. 

When I looked for comfort, I found it everywhere: In my garden, where peonies in every shade of pink erupted in June. On the sidewalks of Litchfield and Kent, which sparkled during the holidays like English villages. Tucking in to chicken pot pie with new friends at a table by the fire at G. W. Tavern, in Washington Depot. Picking up boxes of vegetables at Waldingfield Farm, where both my kids would later harvest Sun Gold tomatoes and snap peas for their first summer jobs. At our beloved Hickory Stick Bookshop, the heart of the community, which one day would host both of my book launches. 

Northwestern Connecticut has historically been a place for free thinkers, celebrities seeking anonymity, writers and artists, and wealthy New Yorkers who are left cold by the splash and glamour of the Hamptons. The abolitionists Harriet Beecher Stowe and John Brown were born here; Marilyn Monroe and Arthur Miller, Stephen Sondheim, and the film director Milos Forman made homes among these softly rolling hills. So have Christine Baranski, Graydon Carter, Daniel Day-Lewis, Denis Leary, Seth Meyers, and Meryl Streep. And while it’s always a thrill to run into a boldfaced name buying a Thanksgiving turkey at New Morning Market, a natural-food store in Woodbury, or gobbling gougères at the White Hart, in Salisbury, we in Litchfield County don’t need the validation of celebrities because, movie star or stonemason, we all live here for the same reasons. 

We relish the starry night skies and the plaintive wail of coyotes. We delight in the crunch of pine needles underfoot when we hike at Steep Rock Preserve. We offer our own heirloom tomatoes or Black Satin dahlias as dinner-party gifts. We meet for a movie at the Bantam Cinema, which sells freshly made popcorn with real butter. We stop at the Warren General Store for the best breakfast sandwich in the world, according to my son, who has sampled quite a few. 

We are hardy around here, and come wintertime, de-icing the windshield is part of the package: we need the cold months for the fruit trees—and our souls—to regenerate. But the release I feel when the orchards burst into life in the spring is hard to put into words. There is nothing quite like the appearance of punch-pink peach and apple blossoms on the ridgeline, and the juicy summer fruit they promise.

One of the things I love to do most of all is show visitors around. And, lately, Litchfield County has gained a couple more reasons for people to come up for the weekend—even if my guest room happens to be full already. Washington’s historic Mayflower Inn, fully renovated after joining the Auberge Resorts Collection back in 2018, has in the past year been joined by two chic boutique properties in Litchfield: the Abner Hotel and the Belden House & Mews. 

I often take guests for a hike at the White Memorial Conservation Center (there are 40 miles of trails) and, later, to explore the area’s gastronomic highlights. That Italian food that was lacking when we first arrived? Well, there is no finer anywhere (even in Manhattan) than Materia Ristorante, in Bantam. I love Litchfield’s West Street Grill for moules frites and Sparrow, in New Milford, for chicken bao buns. Chilling on a bar seat at Community Table, our beloved local restaurant, is like coming home. 

Another delight is to take visitors for wine or music at Spring Hill Vineyards, in New Preston, which has an outstanding art collection (full disclosure, the stone amphitheater was carved by Mark) or to marvel at the home store RT Facts, in Kent. On any given Saturday, there may be an exhibit opening at KMR Arts, in Washington Depot, and a farmers’ market in almost every town.

Some people are surprised that I didn’t lose my identity when I left New York, but in fact thrived, and found a new career as a writer. One dear friend from my New York days paid a visit a while back. She told me that when she arrived, she was expecting to see a country gal churning butter on the porch, hopelessly out of the New York loop. She left looking for real estate. (But yes, I do usually have dirt under my fingernails.) 

It’s not hard to explain: I am the same person I was in New York City, only now I wake up to the sounds of bluebirds, bullfrogs, and wind rustling in the trees. Even though the train to Grand Central is still an hour’s drive away, there is always a play or a restaurant to lure me to Manhattan, which I still cherish, but rarely miss. 

But there are many more reasons to stay, not least of which is the home where I raised my children. They both live overseas, but love returning to see what is popping up in the garden or to catch a glimpse of the bobcat that lives in our woods. 

It would be difficult not to lose your heart to Litchfield County, to what it has always been, and what it is still becoming. There are wonderful new hotels, new stores and galleries, new restaurants, and plenty of specialty shops selling Parmesan cheese.

Unchanging, though, is the backdrop of natural beauty that steals the breath of visitors and, to this day, makes me gasp in awe. When I moved here, feeling displaced and strange and way too removed from city life, I would ask myself, “Whose life am I even living?” Now, when I step outside on a crystalline fall day and the air smells of apples and woodsmoke, I say, “I am so lucky to live here.” 

A version of this story first appeared in the October 2025 issue of Travel + Leisure under the headline “Fall Forward.”