Things to Do in Kent, CT

By VI | Disclosure: I use affiliate links

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If you’re after a New England escape that’s rich in scenery and small-town soul, let me tell you—Kent, Connecticut is where I love to go. When I need a weekend of quiet charm and natural beauty, this is the spot I head for. I’ve hiked to waterfalls, wandered through local galleries, and sipped wine with a view at countryside vineyards. You’ll find Kent has just the right blend of nature, history, and a little luxury. If you’re like me and love peaceful villages with personality, this one’s a gem.

Best Time to Visit

Personally, I think the best times to visit are spring and fall. In the fall, I’ve hiked under blazing foliage with cool, crisp air that makes every trail feel magical. Spring brings out the wildflowers and perfect picnic weather. And if you’re visiting in summer, you’ll love sitting riverside or dining outdoors while taking in those Litchfield Hills views. You can’t go wrong any time of year, really—but those shoulder seasons are something special.

How to Get There

Driving in? I usually drive via Route 7—it’s about two hours from New York City or Hartford. And honestly, the scenic drive through the hills is part of what makes the trip feel like a true escape.
Taking the train? I’ve done the Metro-North Harlem Line to Wassaic before, then grabbed a taxi for the last 25 minutes. Super easy, and a great option if you want to leave the car behind.
Flying in? You can use Bradley International (BDL) near Hartford or Westchester County Airport (HPN)—I’ve flown into both. Each is about 1.5 hours away, and from there you’re just a scenic drive away from Kent’s quiet charm.

Where to Stay

The Inn at Kent Falls – I stayed here for a romantic weekend, and it was absolute perfection. Think antique touches, gourmet breakfasts, and a pool tucked into the woods. You’ll never want to leave.
Club Getaway – When I wanted something more active, this place delivered. With lake access, zip lines, and themed weekend events, it’s ideal if you’re traveling with friends or family and want to mix fun with the outdoors.
Fife 'n Drum Country Inn – I booked this for the food—and I’m glad I did. The inn is cozy and charming, and the attached restaurant serves up some of the best meals I’ve had in town. You’ll love the convenience and the atmosphere.