There’s a stretch of Connecticut that never fails to reset me. A place where winding roads carve through quiet hills and the air smells faintly of grass and nostalgia. I’ve lived in Greenwich for over 20 years, and every year when life feels too digital, I take a Connecticut day trip to Litchfield County. It’s my reset button. A mix of scenic hiking, small-town charm, cheese, chocolate, and autumn foliage, tucked into one impossibly charming corner of New England. Whether you visit in fall or year-round, this is my go-to annual trip.
For a recap of my Connecticut day trip to Litchfield County, see my TikTok below:
🥾 Lovers Leap State Park: Short Hike, Big Views
My Litchfield County road trip starts on a country road dappled with sunlight, or in fall, in gold and crimson leaves. It makes you roll down your window just to hear the crunch of gravel beneath your tires. My first stop: Lovers Leap State Park hike in New Milford.
The trail isn’t long, it's about 1.5 miles round trip, but it’s enough to feel that satisfying burn before the view opens up. From the top, the Housatonic River bends through the trees below like a ribbon of silver. Some call it one of the best hikes in Litchfield County. I wouldn't go as far to say that, but it's an easy hike for all levels with nice views and within driving distance to some great attractions.
☕ Coffee & Small-Town Magic in New Milford
There are many small towns in Connecticut, but New Milford is one of the closest ones to Lovers Leap State Park. A quick pit stop in New Milford feels like stepping into an episode of Gilmore Girls. In fact, you might even think the town is named Sleepy Hollow from all the signage everywhere, but it's actually New Milford. Things to do include exploring the town green lined with antique lampposts, the old-fashioned bookstore that still smells like paper and coffee, and the vintage store. In the fall, every corner glows with pumpkins and gold leaves. Grab a cappuccino, stretch those legs post-hike, and watch locals stroll by.
🧀 Arethusa a Mano: The Grilled Cheese That Ruined All Others
By lunchtime, I’m in Bantam, at Arethusa a Mano, home of the grilled cheese that quite literally ruined all others for me.Slow living has a taste here: buttery bread crackling at the edges, young gouda stretching like silk, and autumn air on your cheeks. This isn’t just any grilled cheese. Arethusa’s young gouda has been crowned Best Cheese in America (2023, 2025), and it shows. It’s the perfect fall fuel after a hike: warm, cheesy comfort wrapped in crackling bread. It's so good, I think it should be in the running for best grilled cheese in Connecticut. Sibby, my 11 month old daughter, would have eaten three if I’d let her.
🍫 Thorncrest Farm: Where Chocolate Has a Name
I follow winding back roads until I reach Thorncrest Farm & Milk House Chocolates in Goshen. It's got to be one of the most unknown and scenic Connecticut fall foliage drives you'll find. Red barns, orange maples, and crisp air make this a perfect autumn stop. It's a trek to get here from Greenwich, CT, so when I make the pilgrimage up here I always make sure to stock up as much as I can.
Thorncrest isn’t just a chocolate shop, it’s a working dairy farm where every cow has a name: Beauty, Magic, Casper, Pepper, Kora and the list goes on. Their milk becomes chocolate next door, a concept they call single-cow-origin chocolate.
I meet Magic's milk in the form of truffles that are creamy, decadent, and impossibly smooth. I buy a few too many and a half gallon of milk to chug them down. We sit on the bench outside the barn eating truffles, sipping milk, and feeling like we’ve just been let in on a secret spell. Sibby practices her walking barefoot on the grass. And behind us are cows and bulls grazing in the field. I'm not romanticizing this, it's reality. Eating outside in the fall air, surrounded by grazing cows, makes you feel like you’ve stepped into a pastoral dream.
🌅 The Drive Home
By the time I’m driving home, the sun has dipped low, painting the fields gold and my car smells like melted cheese and chocolate...a scent I wish I could bottle. I typically do this Connecticut road trip in the fall when the leaves start changing color. This is my annual Litchfield County day trip, my reminder that joy can be simple: a short hike, an award-winning sandwich, a cow named Beauty, and a road that leads absolutely nowhere urgent.
As someone who’s called Greenwich home for over two decades, I can tell you: Connecticut is at its most enchanting in fall, and Litchfield County is where you feel it most.
✨ If You Go
Drive Time: About 2 hours from Greenwich, 2.5 from NYC.
Best Time to Visit: September–November for peak Connecticut fall foliage (also beautiful spring/summer days)
Local Tip: Thorncrest is open limited hours and often sells out of truffles. Call ahead to reserve your favorites, especially anything “Beauty” made.
Related Articles:
