8 Coolest Small Towns in Connecticut for a Summer Vacation (2023)

Connecticut, with its capital city of Hartford, sits bordered by the other western states of Massachusetts, New York, and Rhode Island along the North Atlantic Ocean. It is your year-round cool escape with delicious seafood fare, beautiful fall colors, and some of the nation's most unique beaches.

The Constitution State is home torich cultural heritage, vast manufacturing, Yale University, and ESPN, the American cable sports channel. Visit one of these towns to "connect" withlocal culture and the surrounding naturethrough tons of attractions and outdoor pursuits. You will love the unreplicable experiences and the small-town vibe that these cool places deliver like no other.

More in ConnecticutThe 7 Most Picturesque Small Towns In Connecticut


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Essex is a must-visit charming town for your next summer vacation, with something cool for everyone, especially if you are a die-hard fan of The Gilmore Girls, filmed here in "Stars Hollow." Enjoy strolls through the main street, lined by historic buildings, and the outskirts for scenic drives among authentic farm structures from the Revolutionary War. The First Baptist Church, one of only three in the United States, welcomes visitors with a glorious Egyptian Revival facade and decor that is really pleasing to the eye.

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Families love the old-fashioned tour on the Essex Steam and Essex Clipper dinner trains for a spin through several towns in the area, and Thomas the Tank Engine is a hit with children. Soak in the nostalgic vibe as you inhale salty ocean air from Essex's scenic waterfront along both the Connecticut River and Long Island Sound. Visit the welcoming port town with a plethora of water activities and stay at the Copper Beech or Griswold inns for the best views and amenities. Enjoy a great choice of delicious restaurants for dinner, and stop by the Essex Art Association Gallery for some culture.

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The unique town in Hartford County, along nine miles of the Connecticut River, was named after Glastonbury in Somerset, England. Enjoy easy access fromall major highways for a summer vacation in a one-of-a-kind atmosphere with scenic nature all around. You'll love the vast shopping options in Somerset Square, with thriving businesses and great amenities in a small town feel of just over 34,000. Dive into the riverfront culture with waterside activities, venues, or a combination of both, like the wonderful Riverfront Park.

One of the state's oldest communities with outstanding public education in central Connecticut has a lively, youthful ring and a variety of recreational opportunities. Peruse through pick-your-own-produce venues, casual and fine dining options, breweries, and wineries, and take a ride on the historic river ferry across the Connecticut River for a different view of Glastonbury. Join in on the number ofannual events for all ages, like theSummer Concert Series in the Park in the spring and the Evening Under the Strawberry Moon Festival in the summer. Stay longer for the Apple Harvest Festival in the fall, and come back in the winter to witness the exciting Santa's Run Road Race.


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Madison, set idyllically along the Long Island Sound, is an ideal summertime seaside retreat for every taste, whether you are looking to relax, stay active, or immerse yourself in a small-town atmosphere. There are a ton of outdoor spaces with panoramic views to enjoy nature in your favorite way, like hikes through Hammonasset Beach State Park and the Meigs Point Nature Center.

The Shoreline Greenway Trail is a big hit with any group, for, much like its name implies, there is coastal beauty throughout. Take a stroll or a bike ride amid the Sound's waters and verdant lushness. The compact downtown is filled with adorable bookshops and unique attractions like the Audubon Shop, R.J. Julia Booksellers, and the atmospheric Madison Art Cinema for a one-of-a-kind independent film.


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The picturesque town where Julia Roberts served pies at the "mystic pizza" in the hit movie of the same name is a really cool place to spend a summer vacation. Mystic is full of adorable vibes and a wealth of modern attractions in between retro sights for every taste, like that classic pizza joint, and great shops to visit. With a dozen ways to get out on the water, there are as many aqua-related events, celebrating everything from boats to pirates and schooners.

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The seaside gem of around 5,000 was a former shipbuilding seaport, established in 1684. Mystic's multitude of attractions attracts visitors from around the nation, like the Mystic Aquarium, with its discoveries and great bonding experiences for families. Visit the popular Mystic Seaport Museum for more intriguing insights into this unique town, complete with an old wooden whaling ship. Spend a few hours between its recreated 19th-century fishing village and the children's museum, and take a cruise right from here.

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Old Lyme

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This town with remarkable ecology is an incredible destination for nature lovers and artists alike, as well as for respite seekers from the mundane sights of the city. Enjoy the unique beauty of the wooded hills and meandering estuaries with great hiking and kayaking trails through forests and rivers and access to the Long Island Sound. Come for nature and stay for the small town charm, complete with local gallery hopping, a beach, annual festivals, and regular events like the unique bird walks by the Roger Tory Peterson Estuary Center and a September Swallow Cruise.

Seek out the tiny park along an appealing shoreline for fishing or crabbing, or "fish for sights" from the scenic, handicap-accessible boardwalk. The lovely little town of just over 7,000 has been a flourishing artists' community since the "American Impressionism" movement in the early 1900s. Enjoy downtown strolls under creative vibes and artistic expression, where the natural charm weaves in effortlessly through Old Lyme. Take an art walk through some galleries here, like the renovated and free Studio 80's wonderful outdoor sculpture garden setting.

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Old Saybrook

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Find this charming town, one of the state's oldest and most beautiful, in Middlesex County, the great actress' Katherine Hepburn's birthplace, who was once a resident in Old Saybrook. Visit the Cultural Arts Center, or "the Kate," a legendary top attraction in the area with all things related to the Oscar-winning actress and much more. Check out her former mansion overlooking Long Island Sound on a peninsula with more high-end real estate around for strolls and the cutest public golf course.

Stroll to the Lynde Point lighthouse, one of the most scenic places in the town. Keep with the theme on an art stroll through numerous galleries. Hit Harvey’s Beach for your standard summertime fun and dive into the seafood scene alongside locals at great eateries and fine dining venues in the evening.


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Just 50 miles outside of New York City, Westport is a scenic town along a prime waterfront on Connecticut's Gold Coast, and the Saugatuck River runs directly through downtown. Enjoy world-class shopping and top-notch restaurants on one side and water views on the other. The tiny Main Street features big names like Lululemon, Tiffany's, and J. Crew, while the nationally renowned MOCA Westport is an impressive contemporary art museum specializing in visual and performing arts.

Stop by the renovated Levitt Pavilion, a library and outdoor space with many free summer concerts.Check off various great eateries for dinner while in town and catch an evening show at the Westport Country Playhouse, a stage that once hosted the likes of Paul Newman, James Earl Jones, Robert Redford, and Eartha Kitt. Enjoy a quick escape from the Big Apple any season with hotspots like the Rolnick Observatory, Burying Hill Beach, and Sherwood Island State Park.


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The small, endearing town of Bethel in eastern Connecticut and Danbury‘s southern outskirts is a really cool place to visit for the upcoming summer vacation. It is just 60 miles northeast of New York City and 50 miles southwest of Hartford. There's the epic, 20th-century relic Sycamore Drive-In Restaurant from 1948, with its retro vibe and delicious grub, as well as car cruise night every Saturday from May to September, giveaways, and a DJ. Enjoy the classic 50s atmosphere over a fresh-ground steak burger, frank, or sandwich, and hot rods with the famously homemade root beer, along with a breakfast menu.Bethel, the birthplace of the famous 19th-century showman P.T. Barnum, is a nostalgic and energetic town from 1855, with pedestrian-friendly Greenwood Avenue as its main artery.

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Visit the Bethel Historical Society or take a self-guided excursion through the historic district amid its over two centuries-worth of architectural discoveries.Enjoy drives and nature strolls along the picturesque rolling hills of Fairfield County's countryside. TheBlue Jay Orchards are a must-visit escape of some 140 acres with 36 apple tree varieties. Stay a little longer for the fruit picking season in early September and a farm stand with fresh honey, apple cider donuts, pies, cookies, maple syrup, fruit butters, and more.The headquarters city of Duracell, Bethel, bursts at the seams with cool sights and experiences, like the beautiful sycamore trees and indie movie theater that hosts the annual Connecticut Film Festival.Families can bond over some Monster Mini Golf, Laser Tag, Sky Zone, and the Toy Room.

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Visit these towns for the beach scene and seafood galore, and stay for the artsy vibe and deeply historic centers. Connecticut, which will satisfy all of the summer vacationer's tastes, is home to nationally renowned places like HamptonBeach State Parkin Madison or the MysticAquarium and MysticSeaport Museum inMystic.

Take a state-wide road trip to see all this and more, and just imagine, you can even summer in Katherine Hepburn's roaming grounds in Old Saybrook, which surely imparted some inspiration onto her to win all those Oscars.


Alisa Mala April 7 2023 in Places

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