9 Prettiest Small Towns In Connecticut

Located at the southern tip of New England, Connecticut’s idyllic spot on the shores of the Atlantic Ocean makes it a popular tourist destination. As one of the thirteen original colonies of the United States, many Connecticut towns are well past the three-century mark. However, the history of these iconic New England villages is not the only reason almost 68 million visitors flock to the area each year. A Connecticut road trip promises unmatched beaches and ocean views, unspoiled countryside dotted with historic farmhouses, and acre upon acre of scenic beauty lovingly preserved at State Parks.

Whether you are drawn to the sparkling seaside, long for the serenity of graceful natural settings, want to explore historic sites, or are all about shopping, food, and culture, these pretty towns offer something for every kind of traveler. From Mystic’s coastal charm and acclaimed dining scene to Woodstock’s iconic pink Gothic cottage, the following destinations are sure to inspire your next unforgettable getaway.

Cornwall

A sleepy little town nestled in the foothills of the Berkshire Mountains, Cornwall offers a unique type of pretty. The fiery colors of autumn are the perfect backdrop for one of New England's most sought-after attractions: The iconic covered bridge. Known as the "Home of the Covered Bridge," Cornwall's location on the Housatonic River in Litchfield County is already unbearably perfect, made all the more list-worthy thanks to this delightfully quirky bridge. The beautiful trails at Mohawk State Forest offer unparalleled year-round views of the stunning countryside but are particularly breathtaking in the peak of the fall color season. Be sure to stop in at Cornwall Market on Kent Road S. to stock up on sandwiches and chocolate before hitting the trails. If hiking is too much work, book a reservation at The Pink House, conveniently located just moments from the bridge!

Mystic

Mystic is a Connecticut seaport town where the Mystic River provides scenic beauty. It is exactly what you might picture when you think of a New England seaside town. In fact, this village is every bit a maritime community with its quintessential colonial buildings, ancient sea captain's clapboard cottages, and the weather-worn Mystic Seaport Lighthouse that beckoned them home. However, what is less expected is the James Beard Award-nominated restaurants such as the Oyster Club, a lovely seafood joint.

There is also a selection of art galleries and studios that make this pretty-as-a-picture town unique. If you can only visit one gallery, The Mystic Museum of Art features a carefully curated collection, galleries streaming with natural light, and impressive views overlooking the Mystic River.

Old Saybrook

The name hints at Old Saybrook's storied history as one of Connecticut's oldest towns. While Saybrook Point Resort & Marina helps set the upscale tone for the town, a stroll along Main Street has all the historic feels and ambiance that make this town so pretty. You also can't ignore the seaside views, steady watch of Lynde Point Lighthouse, and oceanfront properties that culminate to create the seaside vibe of the town. Housed in a historic landmark on Main Street, The Katharine Hepburn Cultural Arts Centre, also known as "The Kate," is a museum and theater celebrating silver screen actress and local sensation Katharine Hepburn. You are sure to be delighted you discovered Old Saybrook on the map.

Milford

On a sunny day, the striking reflection of the colorful historic buildings on the Wepawaug River has the magical feel of a painting. White steepled churches, winding boardwalks, sweeping beaches, and Silver Sands State Park all offer exceptional photo ops in a town known for its breweries, water views, and sand dunes. However, two must-see attractions in this part of New Haven County are the castle-like turrets of the historic Milford Memorial Stone Bridge and the scenic Walnut Beach, a local favorite for picnics, sunbathing, and vibrant summer art festivals.

Old Lyme

As the home of the American Impressionist movement, history has shown that New London County's Old Lyme is literally "pretty as a picture." In the early 1900s, American artists flocked to the town to become part of this emerging art movement, including Childe Hassam, Willard Metcalf, Matilda Browne, and William Chadwick. Today, art lovers spend days strolling historic Lyme Street and exploring the halls of notable private galleries and museums. The Florence Griswold Museum is the former home/art colony where the artists of the time lived and worked. While touring the area, you can step into the very landscape and scenery that inspired some of the country’s most influential artists.

Wethersfield

Located in Hartford County, Wethersfield has bragging rights as the home to Connecticut’s largest historic district. As one of the oldest towns in the state, the historic village is centered around the First Church of Christ, built in 1761 with its distinct white steeple, a hallmark of some of Connecticut’s prettiest towns. However, the town also features important landmarks, including the Buttolph-Williams House built in the early 1700s and the homes at the Webb Deane Stevens Museum. Here, the Joseph Webb House, built in 1752, served as General George Washington’s headquarters during the 1781 Wethersfield Conference and his historic meeting with Comte de Rochambeau.

Colebrook

Located in lovely Litchfield County, at first glance, Colebrook is nothing more than a tiny dot on the map. However, what it lacks in population, it more than makes up for with its postcard-perfect scenery. One standout landmark is the Colebrook Congregational Church, a beautiful white-steepled structure that has graced the town green since the early 1800s. Ideal for Sunday drives, the rolling hills, lush green fields, bright red ramshackle historic barns, and natural forests lull you into a quiet sense of serenity. You can also take time to commune with nature, hiking the expansive acreage at Algonquin State Park or take in the breathtaking views at Gaylord Pond or Colebrook River Lake Dams. Although Colebrook is pretty any time of year, it becomes spectacular when the countryside is aflame with fall colors.

Woodstock

A list of the prettiest towns in Connecticut would not be complete without what is perhaps the sweetest cottage in all of New England: Roseland Cottage. Built in 1846, this Gothic Revival cottage draws people to the lovely town of Woodstock year after year. Known for its striking coral-pink façade, the cottage is located across from Woodstock’s common. A visit in the summer includes a stroll through the formal “parterre” garden, and the charming cottage features most of the original Victorian-era interior, including stained glass, wall coverings, and carpets. Afterward, sample local wine at Taylor Brooke Winery’s 44-acre farm, or stroll down the road to visit their taproom to enjoy their selection of local brews. To burn some calories, one can also tee off at the quaint Harrisville Golf Course.

Essex

Located on the Connecticut River, Essex was once known for its rope walks and thriving shipbuilding industry. Part of Essex Township, you can also explore the distinct communities of nearby Centerbrook and Ivoryton to get the whole “Three Village” experience. Historic buildings house shops, inns, and restaurants, and the Main Street is lined with enchanting white picket fences fronting original Colonial-style homes. Local museums and historic sites include the Essex Steam Train and Riverboat Museum, Pratt House, and the Connecticut River Museum.

Final Thoughts

Affectionately known as the “Nutmeg State,” Connecticut towns may be the very definition of pretty. Even the shortest road trips lead to at least one selfie-worthy scene, from red barns dotting the lush green countryside to intriguing main streets drenched in colonial-era history and the weather-worn homes of historic sea captains to shorelines and beaches beyond compare. It is easy to understand how this trendy New England destination continues to attract visitors excited to discover some of the country's fairest towns. Whether you are planning a day trip, weekend getaway, or week's vacation, these nine Connecticut towns should be included in your travels.