10 Best Small Towns In Connecticut For A Crowd-Free Summer
Summer is quickly approaching, and thoughts of a much-anticipated getaway are popping up in the minds of many. Lounging on a beach or leisurely walking through a museum sounds like fun until you realize it seems like everyone else had the same idea at the same time. Then, you find yourself squeezing through groups of people and fighting for parking. Looking for the perfect place to book a summer getaway can be challenging when you wish to avoid the crowds.
Consider making Connecticut the destination for your summertime fun. The New England state is picturesque from one end of the coast to the other, with history just around the corner from seaside fun. Best of all, many of Connecticut’s towns feature small populations, which means a crowd-free summer is in your immediate future. Discover these 10 small towns in Connecticut for a crowd-free summer vacation.
Stonington
Stonington, Connecticut, located in New London County in the southeastern part of the state, features a rich history in the shipbuilding and whaling industries. Now, the town is a center for resort activities. Stonington includes Stonington borough and the villages of Mystic and Pawcatuck. Individuals can find an array of coastal adventures, including stunning trailways, historical landmarks, and gentle surf.
Fennerswood Preserve in Stonington is for nature enthusiasts. The one-way, continuous 0.77-mile trail crosses over stonewalls and a rippling stream and travels through woodlands. Along the way, you can spot numerous birds and land animals. Continue exploring the town’s coastal charm with a visit to the 789. Looming high above the Atlantic for 170 years, the historical lighthouse, made of stone, is a symbol of Stonington’s seafaring past. Catch some waves at DuBois Beach. Located at the southernmost tip of Water Street at Stonington Point, the beach offers gentle waves and views of Stonington Harbor, Fisher’s Island Sound, and Little Narragansett Bay.
Putnam
Positioned on the banks of the Quinebaug River is the quintessential New England town of Putnam, Connecticut. Incorporated in 1855, the city received its namesake after Revolutionary War General Israel Putnam. This little town offers an assortment of activities for everyone, with options suitable for children, antique lovers, classic car fans, and nature enthusiasts.
Just off of South Main Street is the Gertrude Chandler Warner Boxcar Children's Museum, a fun destination for children. Dedicated to the life and work of Gertrude Chandler Warner, the author of the beloved Boxcar Children books, the museum supplies a variety of children's activities, artifacts, and signed books. Putnam is also home to an extensive antiques market. People who appreciate scavenging for old treasures will enjoy Putnam's Antiques Marketplace, which is one of Connecticut's oldest antique malls. Operating since 1991, the mall features 130 antique dealers within its space, offering a range of 18th to 20th-century items, like pottery, vintage jewelry, and more.
Once a year, Putnam hosts an Annual Main Street Car Cruise. The summertime event on August 10, 2025, brings together hot rods, custom vehicles, classic cars, and trucks to encourage car enthusiasts to showcase and enjoy the community's cars at this free, family-friendly event. The great outdoors in Putnam is best at the Quinebaug River Valley. The river trail provides sights and sounds of the waterway, riparian wildlife, and a lush canopy overhead.
Madison
Situated in New Haven County, in the southeastern part of the state, is Madison, Connecticut, a small beach town with enchanting woodlands and a pedestrian-friendly downtown. Madison, established in 1826, is a fun place to visit for a summertime getaway.
Go on a historical journey with a Madison Green Historic District Tour. Throughout the excursion, you will discover 33 significant resources, including historic structures like the 1830 Deacon Benjamin Hart House and the 1916 Sidney Marble House. Relax on the sand or ride the waves at Hammonasset Beach State Park. Two miles of sandy shoreline are prime real estate for sunbathing and strolling. While in Hammonasset Beach State Park, you can learn about local ecosystems at the Meigs Point Nature Center located in the park. Exhibits highlight Connecticut wildlife habitats, ranging from the beach, sky, shore, woods, and water.
Kent
Travel to Kent, Connecticut, for an abundance of fun in the great outdoors. Kent, nestled in the northwest corner of Litchfield County, features a history rooted in farming and the production of iron ore. The city is home to stunning falls, a rolling river, and covered bridges.
One of Kent’s greatest assets is the Kent Falls State Park. The area features a 250-foot waterfall that plunges into the Housatonic River, offering a breathtaking view throughout the various seasons. The Housatonic River lies mostly in the western part of Connecticut and southwestern Massachusetts but also spreads out into small areas in southeast New York. The river is an ideal spot for canoeing, kayaking, and fly fishing activities. Another highlight of Kent is its historic Bulls Bridge, one of the last remaining functional covered bridges in the state. Constructed in 1842, Bulls Bridge provided a means for crossing the Housatonic River from New York state. The area also features rapids, waterfalls, hiking trails, and a small gorge.
Farmington
People who love old buildings and soaking up history will enjoy vacationing in Farmington, Connecticut. Part of Hartford County, Farmington lies in central Connecticut on the banks of the Farmington River. Named for Farmington, England, this little Connecticut town’s early heritage is evident throughout its historical structures.
The National Historic Landmark, the Hill-Stead Museum, is a must-see in Farmington. Spanning 33,000 square feet, the historic building houses unique art and antiques, such as paintings by Claude Monet and Edgar Degas. The grounds also include miles of stonewalls, woodland trails, and a 1920s sunken garden, which is the destination for the summer-long Sunken Garden Poetry Festival. Another historical house worth visiting in Farmington is the Stanley-Whitman House. The living history center and museum teach its visitors about local history in the circa 1720 house, reflecting everyday activities of Colonial life in the area. Outside the house, you can find historic gardens with 17th-century-style garden beds representative of the plants grown by early English settlers and a centuries-old Memento Mori Cemetery. Another notable historical building in the area is the First Church of Christ, Congregational. Located at 75 Main Street, the Greek Revival-style building constructed in 1771 still functions as a fully operational church, with its congregation dating back to 1652.
Westport
Resting at the mouth of the Saugatuck River, east of Norwalk, is the little town of Westport, Connecticut. Settled around 1648, Westport includes Saugatuck and the village of Greens Farms. The town provides a mix of history, natural beauty, and artistry, attracting visitors of all ages.
Discover the history of Westport at the Westport Museum. Established in 1889 to educate others about the town’s history and culture, the museum offers a diverse range of exhibits suitable for people of all ages. Sherwood Island State Park, the state’s first state park, sits on the beautiful Connecticut shoreline, featuring 235 acres of beach, coastal forest, and wetlands. People can swim at the park’s Long Island Sound, fly model airplanes, play disc golf with friends, stop by the 9-11 memorial, and collect seashells across the beach. Attend a show at the Westport Country Playhouse. Initially built as a tannery in 1835, the building later became the playhouse it is now, as a try-out house for Broadway transfers in 1931.
New Canaan
New Canaan, Connecticut, is a vibrant city with a lively downtown and tranquil natural areas. The town is considered a suburb of New York City, which is 45 miles away from the city. New Canaan is part of Fairfield County, located in the southwest portion of the state.
The small city of New Cannan offers an assortment of activities for its residents and visitors. Bask in nature at Waveny Park, 450 acres of parkland and woodlands. The park supplies 3.5 miles of bucolic woodland trails, ample lawns and meadows, and a tranquil pond. Go bird watching at the Bristow Park and Bird Sanctuary, where 17 acres of space provide habitats for an assortment of bird species. The almost 100-year-old park sits a bit south of the New Canaan downtown area and also offers walking trails, an upland hardwood forest, and a duck pond.
Watch locally produced shows at the Summer Theater of New Canaan. Performances include main-stage musicals, plays, and productions performed by local youths and college students. Shop locally made goods at the New Canaan Farmer’s Market. Located on Elm Street, vendors at the market sell local produce and items every Saturday.
Westbrook
Book a getaway to quaint Westbrook, Connecticut, to spend time discovering New England’s natural beauty and history. Westbrook rests in Middlesex County, on the southern side of Connecticut on Long Island Sound. The city was first settled around 1648 and was initially a part of Saybrook Colony.
Breathe in the fresh, salty air at West Beach, the largest of Westbrook’s beaches. The beach offers picnic areas and incredible views of Long Island Sound, Menunketesuck Island, Salt Island, and Duck Island. Check out more of Westbrook’s extraordinary outdoor areas at the Stewart B. McKinney National Wildlife Refuge. The refuge spans 70 miles of the state’s coastline, consisting of ten different units featuring diverse wildlife and ecosystems. You may spot songbirds, wading birds, shorebirds, and other seabirds in their natural habitats. Uncover some of Westbrook’s history at the Adam Stanton House and General Store. Built in 1791, the house and shop feature decorated rooms, several of which showcase original wallpaper, documents, and artifacts.
Old Saybrook
At the mouth of the Connecticut River lies the small town of Old Saybrook, Connecticut. Old Saybrook, named after Lord Say and Sele and Lord Brooke, is a classic coastal city, mixing modern appeal with historic charm. The getaway destination offers delicious local cuisine and breathtaking water views, making it perfect for a summer vacation.
Seaside states offer some of the best seafood options. Dine at Liv’s Oyster Bar for a taste of fresh clams, mussels, and oysters. For 18 years, the establishment has served up fish from the docks of Stonington, Connecticut, and Narragansett, Rhode Island. Finish up your meal with a sweet treat from Fenwick Icecream Co. The locally owned and operated ice cream shop boasts over 30 years of ice cream making, dishing out specialty flavors like Mississippi Mud and Caramel Espresso Bean.
Explore Old Saybrook’s natural beauty at Saybrook Monument Park. Covering nearly 18 acres, about 11 of which are marshland, the park plays a role in the town’s ecology, history, and culture. The area includes a boardwalk and viewing area overlooking the salt marshes and signs scattered throughout explaining Old Saybrook’s history.
Enjoy water views from a Seabird Cruise. Sailing from the Saybrook Point Resort and Marina, the 3-hour cruise rides take passengers up the Connecticut Shoreline and the Connecticut River. You can spot seals and birds in the distance and relax alone or with friends and family.
Old Lyme
Step back in time in Old Lyme, Connecticut, a small New England town rich in history. Located in southeast Connecticut, Old Lyme sits on the mouth of the Connecticut River, where it intersects with Long Island Sound. Once known as Black Hall, the town separated from Saybrook in 1655 and received its current name in 1857.
Take a walk down historic Lyme Street with a self-guided tour to view many of the city’s oldest buildings. On this street, visitors can find the First Congregational Church of 1910, the Charles Ludington House of 1893, and several other historic public spaces and private houses. Even if you stay somewhere else in Old Lyme, be sure to visit the Old Lyme Inn. The fully operational inn, built in 1865 by the Champlain family, provides afternoon tea services every Saturday, lunch at the inn’s restaurant, and a place to enjoy smooth jazz at the property’s Sidecar Jazz Club. Summer adventures are often best enjoyed when they are of the seaside variety. Enjoy the Mystic Seaport Museum in nearby Mystic for a voyage into maritime history. For more than 90 years, the museum has had guests on the 1841 whaleship Charles W. Morgan and taught people about the world of seafaring hundreds of years ago.
By land and sea, Connecticut is full of activities to spend a summer holiday. Whether it is soaking up historical charm by visiting the old buildings on Lyme Street in Old Lyme, checking out the 33,000 square-foot museum in Farmington, or strolling along the Madison Green Historic District Tour in Madison. The natural coastal beauty of the state is prominent in towns like Westbrook, where you can find the Stewart B. McKinney National Wildlife Refuge and Kent Falls State Park in Kent. Family fun opportunities await in Putnam with its Gertrude Chandler Warner Boxcar Children's Museum and Annual Main Street Car Cruise. If you are searching for a town with extra New England charm, Stonington delivers with its Stonington Lighthouse Museum. Local artistry is evident in Westport and New Canaan with their respective theater playhouses. Of course, if being directly on the water is part of your ideal summer getaway, you cannot beat a Seabird Cruise in Old Saybrook going down the Connecticut River. No matter what your perfect summer days look like, Connecticut is full of options.
