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Boat in Mystic Seaport, Connecticut.

These Small Towns in Connecticut Come Alive in Summer

Connecticut is a scenic state nestled along the New England region’s southern end. It boasts a great quality of living, stunning autumn sights, and some of the most delicious food in the region. With all this, the state hosts thousands of tourists who enjoy its sights and attractions. While Connecticut is beautiful year-round, the state truly comes alive in the summer. Housing many interesting small towns with beaches, museums, parks, and more, it is the perfect summer destination.

Kent

water rushing at Kent Falls, Kent, Connecticut
Kent Falls, Kent, Connecticut

Located in Litchfield County, Kent is a quaint town home to about 3,000 people. The town boasts a wellspring of historical value as it was settled in 1739, 37 years before the United States was established! So, if you are into history, check out sites such as Connecticut Antique Machinery Association and Kent Historical Society. Connecticut Antique Machinery Association is a non-profit museum that preserves incredible machinery used in the past centuries. The museum showcases multiple exhibits and occasionally holds outdoor events with all kinds of machinery! On the other hand, the Kent Historical Society provides an in-depth experience of the town’s past. Housing establishments such as the Seven Hearths Home from 1751 find all kinds of restored buildings and fascinating knowledge here.

Step into the future, and you will find that Kent has abundant natural attractions that come alive in the summer. For example, enjoy an entire day at the stunning Kent Falls State Park. This park's prime attraction is the beautiful Kent Falls, a series of waterfalls dropping more than 250 feet! You can spend the day watching the water or hiking along the quarter-mile trail that runs along it. Mixing history with nature, another great spot is Bull’s Bridge. This historic bridge spans 109 feet above the Housatonic River and has been here for more than 170 years!

After all this, you will be looking for a great meal in town. Spend your evening at Fife 'n Drum Restaurant, a joyous place serving locally-sourced ingredients and food for the past 60 years! Or, grab a bite at the local Kent Coffee & Chocolate Company, known for some of the state's best chocolate and baked goods. Overall, Kent is the perfect mix of natural sights and history for a summer vacation!

Chester

Villa Bella Vista, Chester, Connecticut, an old historic home
Villa Bella Vista, Chester, Connecticut. Image credit

Offering small-town vibes with a range of urban amenities, Chester is an ideal summer vacation destination. The town is home to 3,800 people making it the perfect retreat from work and urban stress. Visitors appreciate the picturesque main street's unique architecture, quaint cafes, interesting stores, and more! Spend the day at Norma Terris Theatre, a lovely hall where you can enjoy a range of plays and shows throughout the year. Or, grab a souvenir from the Lori Warner Studio, which boasts finely crafted jewelry, photographs, and prints. No matter what you do, enjoy a refreshing beer at the Little House Brewing Co., which can keep you cool under the summer sun!

Chester also boasts ideal outdoor attractions for the whole family. One of the most famous spots is Chakana Sky Alpacas, a small farm where you can interact with lovely alpacas! These furry animals are super soft and friendly, so you will never get bored of playing with them. If you want a more hands-on nature experience this summer, visit the nearby Cockaponset State Forest. Encompassing more than 17,000 acres of land, this massive natural area is great for rock climbing, hiking, wildlife watching, and various other outdoor activities. So, grab your hiking boots, pack your rock climbing equipment, and head out to Chester this summer!

Greenwich

Greenwich Avenue shopping district in downtown Greenwich.
Greenwich Avenue shopping district. Image credit Brian Logan Photography via Shutterstock

With a vibrant culture and prominent finance industry, Greenwich is a bustling summer destination. Home to a population of 63,000, this town in Fairfield County offers everything from amazing shopping to outdoor activities. To this end, most people spend their time enjoying the stores, cafes, and restaurants nestled along Greenwich Avenue. This posh area embodies high-society shopping; you can find all kinds of luxury stores such as Apple, Manfredi Jewels, and more. If you don’t plan on breaking the bank this summer, opt for a meal at Mediterraneo or Meli-Melo instead. These restaurants have some of the best food in the state and provide a unique ambiance to match the vibe.

If you make it out of Greenwich Avenue’s lovely environment, there is also great outdoor recreation. Greenwich Point Park is a scenic 147-acre natural area with amazing coastal views, peaceful walking trails, and an amazing environment for the summer. On the other hand, Babcock Preserve offers a more immersive experience with 300 acres of swamps, brooks, forests, and dozens of animal species. While these spots are amazing, no summer trip to Greenwich is complete without time along the beach. So, get on a boat to the nearby Island Beach, which offers sandy shores and clear water, perfect for waterside fun!

Mystic

Boats in the harbor in Mystic seaport, Connecticut
Mystic seaport, Connecticut.

When you think of an ideal summer destination, Mystic is probably what comes to mind. Often ranked as one of America’s top summer destinations, this town in Connecticut is a coastal wonderland. Once a prominent seaport where more than 600 ships were built, Mystic has a strong connection to its immense coastline. So, take in the immense maritime past by visiting sights like the Mystic Seaport Museum. This museum boasts an amazing collection of ships, boats, and artifacts from Mystic’s maritime past. Or, check out the Old Lighthouse Museum, built inside a lighthouse from 1840! While the lighthouse is now decommissioned, it is well preserved, showcasing the keeper’s quarters and steps.

After learning about the local history, it's time to see why Mystic is known as one of the best beach towns. A trip to the local DuBois Beach is the perfect way to have fun in the sun. You can spend a whole day here with lifeguarded beaches, scenic shores, and many small stores. For a more adrenaline-filled experience, hop on to a boat at Mystic Boat Adventures to enjoy the water up close. While the beaches are amazing, be sure not to stay out in the hot sun for too long. Instead, you can visit Mystic Aquarium, a top attraction for families in the town. With hundreds of amazing marine animals and fun touch tanks, your kids will surely enjoy a day at the aquarium. From the maritime history to the coastal attractions, there is no end to the summer fun you can have in Mystic.

Glastonbury

Channel marker on the Connecticut River near Glastonbury, Connecticut, on a sunny June day.
Connecticut River near Glastonbury, Connecticut, on a sunny June day.

Nestled along the banks of the Connecticut River, Glastonbury is a lovely waterside town in the state. Home to a population of 35,000, this town combines vibrant culture and coastal sights. Glastonbury has you covered with its historic district for a lively place to make new friends and learn about the local culture. This 128-acre area boasts over 100 buildings where you can witness unique Colonial and Greek, architecture styles, learn about the past, and meet new people. Some houses here have been around for more than 200 years, making it a real blast to the past. If you are in Glastonbury with family, Rose’s Berry Farm is another great option. Opened in 1908, you can pick strawberries, apples, blackberries, and other fruits — fun for the whole family.

In addition to this, Glastonbury has great spots to chill out and enjoy the summer sun. For example, Cotton Hollow Preserve is a serene location that provides relief from the urban hustle and bustle. Offering a secluded natural area and activities such as hiking, biking, and fishing, you can enjoy Mother Nature without any distractions. End your trip at Blackledge Falls, a local waterfall hotspot for tourists. The falls drop more than 25 feet from cliffs providing a stunning sight you can watch for hours on end.

Westport

Westport Connecticut Downtown Bridge
Westport Connecticut, downtown river bridge.

Just 50 miles from New York City, Westport is the perfect summer retreat for New Yorkers. Offering waterside views along Connecticut’s Gold Coast combined with amazing shopping and culture, Westport comes alive during summer. The main shopping district is a must-visit, filled with tourists, and boasting hundreds of locally owned stores, luxury outlets, cafes, and restaurants. So, you can buy souvenirs for your friends, have a coffee at GG & Joe, or roam around and take in the positive vibes. While you are sure to find everything you need in Main Street, the nearby Chuch Lane, and Bedford Square also boast cute establishments, so you will never run out of options in Westport.

Due to its coastal location, hitting the water is almost compulsory if you are visiting Westport. So, get away from the summer heat by taking a dip at Compo Beach. With calm and clear waters, you will surely lose track of time in the water. The beach also has volleyball courts, basketball courts, and a marina for various fun outdoor activities. For someplace more quiet, you can enjoy Sherwood Island State Park instead. This 235-acre park offers a lovely beach that is much quieter, making it the perfect place to set up a chair and sunbathe throughout the day. So, for amazing shopping and beautiful beaches, Westport is the summer destination.

New Canaan

Daytime view of a street in the downtown area of New Canaan, Connecticut during the summer season
The downtown area of New Canaan, Connecticut, during the summer season. Image credit barbsimages via Shutterstock

The embodiment of a luxurious summer retreat, New Canaan is one of the wealthiest towns in the state. With one of the highest median incomes in the country, there is no shortage of classy sights and comfortable attractions in this town. Enjoy the amazing vibe with a visit to Mead Memorial Park. This park features a range of activities such as tennis, ice skating, baseball, and even pickleball. Hang out with your friends and family for an active day out in the sun.

If you would rather spend the day indoors, take a look at the cultural attractions, such as Silvermine Arts Center and the Philip Johnson Glass House. The Silvermine Arts Center is a prime example of the budding arts scene, with more than five galleries of unique and beautiful artwork. Taking a step further, the Philip Johnson Glass House is a unique home with transparent glass walls. The interesting openness and symmetrical structure have made this a top spot for tourists coming into New Canaan.

Any summer in New Canaan is incomplete without a trip to Elm Street. This upscale neighborhood is a treasure trove of the state's best stores, cafes, and restaurants. So, grab gifts for your friends at the famous Adirondack Store & Gallery, or treat yourself to luxurious jewelry at Pennyweights. If you’re feeling hungry, there are amazing spots to eat throughout Elm Street. The best options you need to try are Baldanza and Ching’s Table, which offer everything from delicious food to great service. Combine it all, and you can see why New Canaan comes alive during summer.

Colebrook

Colebrook, Connecticut, The Hale barn, a typical barn construction from the 18th century.
 The Hale barn, Colebrook.

Encompassed by the scenic Litchfield Hills, Colebrook is a small town rich with natural beauty. To this end, tourists from all over flock to the town during summer for a relaxing retreat from urban life. One of the most popular spots in town is Colebrook River Lake. The 700-acre lake offers an amazing environment with panoramic views of the surrounding hills. Along with this, both fishing and boating are allowed so you can plan out a fun fishing trip with your friends! For a less watery experience, the nearby Algonquin State Forest is a treasure trove of natural beauty. Encompassing nearly 3,000 acres, you can find everything from amazing wildlife to stunning forests here. Moreover, the forest offers opportunities for wildlife viewing, hiking, and more, making it any nature lover’s dream.

While a summer spent outdoors is fun, you might also want to enjoy some food and drinks. Well, why not mix both of these things at Norbrook Farm Brewery? This unique attraction boasts a large farm as well as a brewery with some of the best beers in the region! So, you can walk along the trail, play with farm animals, and chug beer right after. If you get hungry after all this hard work, have a bite at one of the food trucks for a summer you will never forget.

Whether it is natural beauty or historical value, these amazing towns in Connecticut come alive during the summer. Providing visitors with a range of amenities and attractions, there is no end to the fun you can have in these small towns. That said, be sure to book your trip in advance as the summer traffic in these towns can get out of hand!

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