Charm Alert Last Updated 7/16

With its appealing historic architecture, village greens and tidy shops, Connecticut still does “charming” very well. In fact, there are immensely attractive little towns all across the state that - with their shops, restaurants, galleries and inns - are perfect for a visit and even an overnight this fall.


Chester is a lovely little town on the west bank of the Connecticut River, surrounded by valley hills and with a center of town that’s right out of central casting. You’ll find yourself charmed by places like The Good Elephant Bistro or New American River Tavern, galleries such as Connecticut River Artisans and Chester Gallery and shops like Ceramica. And be sure to make a river crossing on the Chester/Hadlyme Ferry.

Stonington Borough

The Village, as it’s called locally, is unlike any other place in the state - in fact, someone once wrote that it’s as if a piece of Nantucket had somehow separated itself and floated down to this southeast corner of Connecticut. Here, among its narrow lanes, the story of Stonington and the sea is everywhere, and it’s even home to Connecticut’s last remaining fishing boat fleet. Try an overnight at The Inn at Stonington, a meal at Noah’s and a visit to the Old Lighthouse Museum and you’ll soon feel right at home.

New Preston

This tiny town is situated on the shore of Lake Waramaug, arguably Connecticut’s loveliest lake, where the colors blaze in the fall. There are shops in the tiny town, and a restaurant or two as well, such The Hopkins Inn and the nearby Community Table. And you should certainly drive, bike or hike the 8-mile loop around the lake and stop at Hopkins Vineyard along the way.

Rowayton and Southport

These affluent villages are part of the larger Fairfield County towns of Norwalk and Fairfield, respectively. Each features a MetroNorth station, water views in all directions, quiet streets and lanes, interesting residential and civic architecture and just enough shops and restaurants to make life interesting. Stroll through the ever-changing galleries of the Rowayton Arts Center. In Southport, stay a night at the stylish Delamar Southport which features a spa and the Artisan Restaurant, Tavern & Garden. 


Pomfret will give you a real taste of how charming Northeast Connecticut can be. There is history at every turn of the road here, and much of it has been preserved in the houses and public buildings. There are long views and nature walks at the Connecticut Audobon Center in Pomfret, but also galleries and shops, bed & breakfasts and eateries like the Vanilla Bean Café, that are, in a word, charming.