Litchfield, Connecticut

By VI | Disclosure: I use affiliate links

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If you’re dreaming of a New England escape that feels like a breath of fresh air, let me tell you about Litchfield. I’ve explored its winding backroads, wandered through historic districts, and sipped coffee at its coziest cafés—and honestly, I think you’d love it. Tucked into the scenic hills of northwestern Connecticut, this town has a way of blending charm and calm like nowhere else I’ve been. Whether you’re hunting for antiques or lacing up for a trail walk, Litchfield’s got something for both your soul and your camera roll.

Best Time to Visit

If I had to choose, I’d say spring and fall are when Litchfield really shows off. I’ve visited during those months, and it’s pure magic—blossoms in May, blazing trees in October, and a kind of peaceful energy that makes you want to stay awhile. That’s when I like to hit the trails or browse the local festivals. You’ll find fewer crowds and more color, which is always a win in my book.

How to Get There

If you’re driving: I usually head up Route 202 or Route 63—it’s a beautiful drive no matter the season. From New York City, you’re looking at around 2 hours. Boston’s about 2.5 hours out. Easy road trip distance if you ask me.
By Train: When I’ve taken public transit, I’ve hopped on a Metro-North train to Waterbury. From there, it’s about a 30-minute drive to Litchfield. If you’re up for a little adventure, it’s totally doable.
By Plane: If you’re flying in, I recommend Bradley International Airport (BDL) near Hartford. I’ve made that drive in under an hour, and it’s a straight shot with pretty views along the way.

Where to Stay

Litchfield Inn – I’ve stayed here for quick getaways, and I love how close it is to everything. The rooms feel polished but still warm, and you’re just minutes from downtown shops and dining.
The Inn at Mount Pleasant Farm – If you’re looking for something extra peaceful, this B&B is a gem. I remember waking up to open fields and birdsong—such a lovely way to start the day. You’ll feel tucked away in all the best ways.
Tollgate Hill Inn – This one’s perfect if you love colonial charm. I’ve walked through its creaky halls and admired the beams overhead—it’s got that cozy, lived-in feeling that makes it feel more like a home than a hotel.