Covered bridge over Falls Brook at Kent Falls State Park.

9 Top-Rated Small Towns In Connecticut

Connecticut also referred to as the 'Nutmeg State,' is among the smallest states in the US and yet has abundant natural beauty in the form of sandy beaches, flourishing forests, effervescent lakes, and stunning waterfalls. Amazingly, all this beauty is contained in its cute little towns worth visiting for a relaxing vacation or even a weekend getaway. Featuring historical heritage in quaint Chester, while Cornwall boasts the beautiful Berkshire Mountains, any trip to Connecticut will surely please visitors! To help plan a trip, discover the following nine top-rated small towns in Connecticut!


An empty road after a March snowfall in Chester, Connecticut.
An empty road after a March snowfall in Chester, Connecticut. Image credit Joe Tabacca via Shutterstock.

Chester, located in Middlesex County, is known for its beautiful historical heritage. When visiting Chester, travelers will come across several ancient buildings and houses that have consciously been preserved and protected. One such building is the Old Town Hall. Furthermore, it is worth mentioning that Chester is the perfect destination for a romantic weekend getaway! The town boasts several boutiques and galleries and has a strong theater culture, perfect for lovebirds. Also, it has the most scenic topography and offers excellent walking and hiking areas close to the town. Some must-visit places in Chester include the Cockaponset State Forest, Norma Terris Theater, and Chester Museum at the Mill/Chester Historical Society.


Covered bridge over Falls Brook at Kent Falls State Park
Covered bridge over Falls Brook at Kent Falls State Park.

For folks looking for the perfect blend of the old and the new, Kent should be the following weekend's getaway destination. With its beautiful rugged landscape, this town is quaint and charming and can be visited anytime. Kent mainly because it offers something to every kind of traveler. The local boutiques sell an array of exclusive and stylish goods that shoppers will want to take home as souvenirs from the trip. Also, do not forget the cozy restaurants serving delicious food made with fresh local ingredients. Visiting the Kent Falls State Park is a must if outdoor adventure beckons. This place has trails, covered bridges, and stunning waterfalls!


Beautiful St Bridget's Church Est. 1883 near Housatonic River
St Bridget's Church near Housatonic River in Cornwall, Connecticut. Image credit Miro Vrlik Photography via Shutterstock.

Cornwall is another famous small town in Litchfield County, Connecticut. It is surrounded by the lovely Housatonic River and Berkshire Mountains and is deemed the greenest town in Connecticut. Cornwall is an ideal weekend getaway destination because it allows visitors to enjoy a vibrant culture in a quaint, peaceful environment. Hiking, rafting, and fishing are some of the outdoor activities that travelers can enjoy in the Mohawk State Forest during their stay in Cornwall. Another popular attraction is the West Cornwall Covered Bridge, among the few covered bridges in the state. Need a little more adventure in your weekend getaway? Plan a visit in the winter season and try skiing at the Mohawk Mountain!

New Canaan

Walkway with store fronts and autumn decoration in nice sunny day
Walkway with storefronts in New Canaan. Image credit Miro Vrlik Photography via Shutterstock.

Only an hour's drive from New York City, New Canaan is situated in Fairfield County and is among the most sought-after small towns in New Canaan. The city's key attraction is the Glass House, the home of Philip Johnson, who also designed this eclectic spot. Another must-visit stop in New Canaan is the New Canaan Museum & Historical Society, home to eight historical structures! Most tourists enjoy a tour of the 1845 Cody Pharmacy, built in 1845 and continues to retain its original old merchandise, fixtures, and bottles. The property has a nice walking trail that takes people to the various exhibits (the interactive signs make the walk even more enjoyable!). For a lunch break, find a table at Rosie's and savor a delicious meal! There is a walking trail that leads to the exhibits with interactive signs that help make this a great family-friendly outing!


American flags and a white picket fence line Main Street in Essex, an all-American village.
Main Street in Essex, an all-American village. Image credit Jeff Holcombe via Shutterstock.

Located in Middlesex County, Essex is a lively little town in Connecticut. Visitors will find all the activity in its famous town center, which has several small streets with restaurants, shops, and galleries to explore. If you are craving a sumptuous hot meal, Griswold Inn is the place for you, and if art is what ignites your interest, then a visit to the Connecticut River Museum will be sure to please. After all the activity, take some time to sit back and enjoy the bounty of nature that the parks in Essex have to offer. 


Fall foliage and golden wetlands vegetation, with sun rays on the shore of Black Spruce Pond in the Goodwin State Forest in Chaplin, Connecticut.
Fall foliage in Goodwin State Forest, Goodwin, Connecticut.

The essence of Chaplin, a splendid town located in Windham County, cannot be captured in a paragraph. This small town must be visited to experience its beauty and charm fully. Sprawled with spacious lawns, red brick homes, and trees that turn shades of orange every autumn, Chaplin is a great spot to consider for a weekend getaway. There are some lovely places to stay in Chaplin (check out the Stone Arches Bed & Breakfast and Henrietta House Bed and Breakfast), and the town is exceptionally well-maintained. Travelers here will find a lot of Georgian architecture reminiscent of the early 19th century. Spend a day visiting the Witter House and Chaplin Historic District; the perfect activity for history enthusiasts!


Aerial view of coastal community and beach of Fairfield, Connecticut
Aerial view of the coastal community and beach of Fairfield, Connecticut.

For those who have yet to travel to the Gold Coast of Connecticut, this is the sign to do it now! Why? It is home to an enticing little town called Fairfield, which can best be described as paradisical for a romantic weekend getaway. Dip your feet into the expansive sandy beaches and savor delectable food at the best-rated restaurants in the town. You can park for a day full of sunshine at five different beaches in Fairfield. These are ideal for a relaxing dip in the water followed by a nice little picnic. Other popular places in Fairfield include the Fairfield Farmers' Market, the Old Post Road Historic District, and the Fairfield Museum and History Center.


Blue hour after sunset in Madison Connecticut from East Wharf beach
Blue hour after sunset in Madison, Connecticut.

For those who love coastal beach towns, Madison in New Haven County is just that. Home to the gorgeous Hammonasset Beach State Park, featuring pristine beaches running for about two miles, this beach is a major tourist attraction. Nature lovers can continue their outdoor exploring with a visit to Meigs Point or perhaps a nice walk or biking adventure on the Shoreline Greenway trail. Make a pit stop at the Clam Castle or Lenny & Joe's Fish Tale for local seafood! It is no wonder Madison is a top-rated Connecticut town!

Old Saybrook

View of the Saybrook Beach with colorful kayaks on the shore in the distance
View of the Saybrook Beach.

True to its name, Old Saybrook is among Connecticut's oldest and most scenic towns. Many people remember it as the home of Hollywood star Katherine Hepburn once upon a time. Unsurprisingly, the town's Cultural Arts Center is named after the Oscar-winning actress. Other must-visit spots in the city include Lynde Point, a lighthouse visitors can walk down to explore. There is also Florence Griswold House, now a museum overlooking the gleaming Lieutenant River.

It would be safe to say that these small coastal towns of Connecticut make for the perfect weekend getaway destinations for couples and families. With their intriguing history, local culture, natural beauty, and diverse food offerings, these towns bring together New York's sophistication and New England's traditions in the best way possible!

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