Best Towns in the Litchfield Hills

There are no cities in the Litchfield Hills.  If you're looking for a vibrant nightlife or a bustling street scene, you're looking in the wrong place.  That said, amidst the collection of charming towns and villages in the region, there is a distinction that can be made for a few of them.  These select few provide enough activity, history, and points of interest that they can be seen as a true destination that can be enjoyed for more than just their beauty or the relaxing slow pace of life that they offer.

The Destinations




Centered on a beautiful village green, Litchfield is the most obvious destination in this region of hills that bear the town’s name.  There are plenty of boutique shops, the best collection of restaurants in the area face the green, and the streets radiating from the center of town are lined with beautiful homes and churches. 

A visit allows you to tap into Litchfield’s rich history - America’s first law school was founded here before the revolution, and the town is the birthplace of Harriet Beecher Stowe and her brother Henry Ward Beecher – while enjoying the modern comforts.





Kent is the best and most convenient jumping off point to some of the main “attractions” of the Litchfield Hills – Kent Falls State Park, Bull’s Bridge, Lake Waramaug, the Appalachian Trail along the Housatonic, and Macedonia Brook State Park are all close at hand – but it’s more than that as well. 

The quaint town center has restaurants, antiques, an independent book store, a great chocolate shop, and an array of art galleries to keep you interested between jaunts to the surrounding natural wonders. 




Woodbury is one of the oldest settlements in the Litchfield Hills with some buildings dating back to the 1600’s, and its fascination with old things comes through in the collection of antique shops that line Main Street.  It also has its fair share of historic and picturesque churches

The town itself is small and quaint, but a convenient location just North of I-84 allows you to have some modern conveniences close at hand if needed.   

Other Stops


New Preston

A brook runs through the center of this tiny crossroads that sits right below Lake Waramaug.  A stop here is great for antique shoppers, and the town has a good selection of cafes and restaurants for its small size. 


Like many other towns in the region, the village green and church are the centerpiece of this well-preserved town in the southern Litchfield Hills.  It also has the distinction of being the first town in the United States to be renamed in honor of General Washington in 1179, two years before the end of the war.


This traditional summer retreat in the Northern Litchfield Hills is a quiet town with, you’ll never guess, a beautiful green/church combination and a nice converted train station.  It’s surrounded by some great rolling hills and farmland, especially West down Hwy. 44, and it’s within easy reach of some great spots like Campbell Falls and the Berkhamsted Reservoir.


We’re not going to pretend that there’s really anything to “do” in Sharon, but this charming town is a sight to see.  In a visit to this single strip along Main St. (Hwy. 41), you’ll take in a village green, a war memorial, several brick and white-clad colonials, a 19th century stone clock tower, and a couple beautiful New England churches.

New Milford

The Southern gateway to the Litchfield Hills, New Milford is the closest thing to a city that this region has.  Despite the fact that you’ll find slightly more conventional shopping and chain restaurants, it does have a charming town center and a great collection of restaurants.  It’s also the most accessible entry point to the Litchfield Hills from New York City and all points South.


This quiet town in the extreme Northwest corner of the state includes the fun hamlet of Lakeville and provides great access to both the surrounding lakes and the famous Appalachian Trail. 





New Preston

New Preston