Nowhere else in America has as many cute little towns as New England. Of all the states,  you’ll find some of the cutest small towns in the tiny state of Connecticut!  In many of these towns, you are likely to explore destinations that embody pertinent historical landmarks and local traditions happening every year.

A mention of Essex, CT, is the only way to start a list of the cutest small towns in CT. You’ll soon realize why it was voted one of the “best small towns in America.” The small-town charm captivates all who visit to experience a historic riverside town.



Nestled inside the Connecticut River Valley, the town of Chester will quickly become your favorite.  Whether driving into town through the lush forest region or cruising in on the Chester/Hadlyme Ferry, you’ll be blown away by its charm the moment you lay eyes on it.


Many people consider Kent to be an escape from the big city. With just a short train ride from New York City, the bustling metropolis views will quickly transform into lavish natural scenery.  The cute town of Kent not only has visual appeal but there are plenty of fun things to do around town.


Mystic was once one of the most important seaports in Connecticut. Much of the maritime history is preserved in the Mystic Seaport Museum. Exhibitions detail lots of information about its history.  And just outside the building are several preserved ship museums, many of which are listed on the National Register of Historic Places.

Madison is one of the larger towns on this list, with over 18,000 people living there. But what will really blow your mind is that every year, it receives over one million visitors – a majority arriving during the peak summer season.  If you couldn’t figure it out by now, Madison is a cute town with picturesque beaches lining the entire shoreline.


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