View from Westport bridge over Saugatuck River and architecture near downtown on a beautiful spring day. Editorial credit: Miro Vrlik Photography /

The Most Picturesque Small Towns in Connecticut

Connecticut is a southern New England state in the U.S. with the prettiest towns worth exploring and enjoying. With so many interesting commercial locales and natural or historical landmarks within each town, it is safe to say that travelers will always have something to see and do while visiting and taking it all in as outsiders with a newfound experience to unravel. These picturesque towns will leave one truly speechless!


Scenic fall view of Redwing Pond at Ansonia Nature Center.
Scenic fall view of Redwing Pond at Ansonia Nature Center.

A small town on the Naugatuck River with 18,954 residents, Ansonia is home to some pretty natural parks and outdoor thrills. Ansonia Nature & Recreation Center is a big stop for tourists who want to enjoy 156 acres of woodlands with various pond species, as well as amazing sunrises and sunsets! At Abe Stone Park, visitors can find serenity and nature fused as they unwind under shady areas and enjoy scenic walks.

For history lovers, Derby Historical Society offers American Revolutionary War knowledge and the heritage of David Humphreys, a close friend of former U.S. president George Washington. Those seeking some scenic views within an indoor atmosphere can visit the Church of the Assumption, a famous stop for locals and tourists who love to hear the sounds of choirs and masses as they represent parish culture and 18th-century upbringing. For hungry stomachs, Copper City Bar & Grill provides a vibrant dining experience with the best local cocktails and custom comfort dishes around!


Westport, Connecticut, USA: View of Church Lane on a beautiful spring day with Patagonia and Anthropologie stores.
Westport, Connecticut, USA. Editorial credit: Miro Vrlik Photography /

Westport is a town of 2,378 locals who love having natural splendors around. The 29-acre Compo Beach is a must-see for beachside photography and Long Island Sound sandy recreation. Sherwood Island is another hotspot for marshland exploration, seashell collecting, and birdwatching. Earthplace may be more up the alley for those needing a peaceful or relaxing wildlife sanctuary with dozens of walking trails and a cool outdoor amphitheater surrounded by picnic groves.

Entertainment fans will want to stop by Westport Country Playhouse for unique performances and cultural shows that bring out the best of this town. The Westport Observatory is perfect for solar system enthusiasts and those who love a bit of astronomy while viewing the stars at night. Paci Restaurant has splendid Italian cuisine for tourists who love grilled shrimp salads with a fresh slice of coconut cake on the side.


Panoramic view of historic homes along the Mystic River during a vibrant sunrise in Mystic, Stonington, Connecticut.
The Mystic River in Mystic, Stonington, Connecticut. Editorial credit: EB Adventure Photography /

Stonington is a town of 1,007 inhabitants that has plenty of attractive landmarks and locales. The Stonington Lighthouse is a typical stop for tourists with its 18th-century stone architecture and dramatic Long Island Sound viewpoints. Captain Nathaniel B. Palmer's House Museum is another historical stop that is guaranteed to bring awes and smiles with its 1850s Greek Revivalism and Victorian-era ship relics once belonging to a famous captain!

Saltwater Farm Vineyard offers natural sights and farmland scenery while visitors enjoy award-winning wines and learn about its history as a World War II airplane hangar. For those looking for a picturesque itinerary with some happy conversations around religious scholars, Enders Island has a cozy retreat area for tourists and residents to take in beautiful chapel scenery and solitary serenity at the same time. Wholesome dining pleasures can be had at Noah's Restaurant, a famous stop for traditional onion soups and the best coastal pies.


Beachfront homes with sand and waves in Madison, Connecticut.
Beachfront homes in Madison, Connecticut. By Léo Schmitt, CC BY-SA 4.0, Wikimedia Commons

A south-central town with 17,742 residents, Madison is a lovely destination for tourists. Hammonasset Beach State Park is a big motivator for those in town who crave serene preserves and sweeping views while cycling around Long Island Sound. Shoreline Greenway Trail is ideal for hikers and joggers who want to take on easy terrain with estuary sightseeing and marshland appreciation. For others, Salt Meadow Park may be more thrilling with its old airport runway foundation and captivating coastal forest routes!

Farmland tranquility can be found at Field House Farm, where downtown social vibes and easygoing family-friendly activities create a meaningful itinerary. Visitors stopping by Susan Powell Fine Art may find beautiful flower arrangements at the entrance while going inside to explore famous Realism artworks and abstract paintings of New York City. Bar Bouchee has the best French cuisine to satisfy those needing a quaint dinner, while The Wharf Restaurant has the most spectacular waterfront scenery for anyone who loves to eat delicious New England seafood!

New Canaan

Downtown New Canaan, Connecticut, USA.
Downtown New Canaan, Connecticut, USA. Editorial credit: Miro Vrlik Photography /

Only an hour away from New York City by train, New Canaan is considered home to 19,880 locals. Waveny Park is an easygoing landmark with 19th-century ponds and trails that make for a memorable trip for anyone seeking wildflower scenery and birdwatching exposure. Irwin Park also makes tourists feel at home with its cozy bench areas surrounded by vast lawns full of sunlit vegetation and pretty apple orchards! For even more natural splendors, one can visit Browne Wildlife Sanctuary to see expansive farm territories and glacial boulders.

The New Canaan Museum & Historical Society is a mid-century landmark where visitors can tour World War II relics and Colonial era manuscripts of the past. At the Glass House, historic 1940s architecture and residential artworks make for an interesting exhibit. The Summer Theatre of New Canaan is no stranger to theatre entertainment as it provides local summer programs and live shows for all audiences to enjoy. Fans of Chinese cuisine and large buffets can satisfy their stomachs at Ching's Table, while others can enjoy Pesca Peruvian Bistro's hidden gem dishes that capture the essence of South America!

Old Saybrook

Sunset view of boats and houses along the coast in Old Saybrook, Connecticut.
The coast in Old Saybrook, Connecticut. Editorial credit: Wirestock Creators /

A small town of 10,363 residents, Old Saybrook is a top contender for coastal sights in the lower part of the state. Harvey's Beach has amazing high tides and sandy walking paths for visitors needing a day for sunsets and seashell hunting. On Shelter Island, Wahel's Tail is a great extracurricular option for anyone who loves mini-golfing while taking in Connecticut River delights! Clark Community Park has peaceful roaming areas for newcomers who love fishing and hiking and also includes common birding paths for taking in solitude and avian pleasures.

General William Hart House is a historical detour with 17th-century Georgian colonial architecture and Revoluition-era fireplaces that make for a cozy yet immersive experience! Classic American cuisine is always around for travelers who eat at Monkey Farm, where shoreline locals love talking about the natural beauties of the state. Fromage Fine Foods & Coffee is likely to keep tourists around with its one-of-a-kind cheese goods and gourmet foods.


Foliage season in Litchfield Hills, Winsted, Connecticut, USA.
Foliage season in Litchfield Hills, Winsted, Connecticut, USA.

A northwestern town of 1,220 residents, Litchfield is known for its hiker-friendly landmarks and serene stops. The White Memorial Conservation Center is recognized for its 4,000 acres of unparalleled beauty stemming from the White Memorial Foundation's various hiking trails, leisure-filled routes, and big brown bats that can always be seen at the barns each evening! The Topsmead State Park is another gracious landmark with 19th-century meadows and flower gardens with casual picnicking and cross-country skiing pleasures for newcomers.

Nature lovers who would much rather be in smaller wetland environments can enjoy Little Pond Boardwalk Trail, a comfortable wooden walkway with easy access to the Bantam River and migratory birds. At Lee's Riding Stables in Windfield Morgan Farm, tourists can take part in horseback adventures and witness the true backcountry of town. For those with a sweet tooth, Peaches N' Cream has mouthwatering ice cream flavors and desserts to please travelers from all over!

Final Thoughts on Connecticut's Scenic Small Towns

These small towns are all best for any traveler needing a picturesque itinerary in the New England region. The "Constitution State" is not unfamiliar with tourism and beauty. Connecticut is truly scenic in many ways with countless locales and landmarks to appeal to any traveler from all wakes of life. With this list handy, travelers will fall in love with these towns!

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