Top 9 Best Small Towns in Connecticut

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Connecticut may be the third-smallest state, but its enthralling borders are home to a wealth of scenic landscapes and charming small towns. The Nutmeg State ... read more...

  1. Top 1

    Mystic

    On the Mystic River in Connecticut, the quaint village of Mystic can be found. A popular summer vacation spot in New England a region with beautiful scenery, seaport museums, historic homes, and charming shops is home to both tourists and locals. The bascule bridge where U.S. Route 1 crosses the Mystic River serves as the focal point of the community. In 1920, the bridge was constructed. Watching the bridge raise and lower with its massive counterweights, gears, and bridge tender's residence is amazing.


    Connecticut's Historic Mystic was a prominent seaport in the late 1700s. The Seaport is currently one of the country's biggest maritime museums. Four National Historic Landmark vessels are housed there. Among them is the Charles W. Morgan whaleship, built in 1841, which is the oldest merchant ship in the nation. The Mystic Seaport Museum is must-see. A functioning shipyard and a faithfully recreated seafaring village from the 19th century can be found in this historic harbor. You can find out how sailors constructed ships, where they lived and slept, and how they turned whale blubber into fuel at the museum.


    There is a "touch pool" at the aquarium where you can pet stingrays, sharks, or starfish. Countless indoor and outdoor exhibits featuring jellyfish, turtles, sea lions, and other marine life are also available. Additionally, make sure to see Deep Sea 3D and Return to the Titanic. Make sure to visit the Animal Rescue Center, where you can see rescued, seals being treated, before you leave the Aquarium. Check out all the exciting events the Aquarium hosts in advance, such as overnight stays and cocktails with the whales, before making travel arrangements to the aquarium.

    Photo by  Rusty Watson  on Unsplush
    Photo by Rusty Watson on Unsplush
    Photo by Rusty Watson on Unsplush
    Photo by Rusty Watson on Unsplush

  2. Chester is a town in Middlesex County, Connecticut, United States. There is a "touch pool" at the aquarium where you can pet stingrays, sharks, or starfish. Countless indoor and outdoor exhibits featuring jellyfish, turtles, sea lions, and other marine life are also available. Additionally, make sure to see Deep Sea 3D and Return to the Titanic. Make sure to visit the Animal Rescue Center, where you can see rescued, seals being treated, before you leave the Aquarium. Check out all the exciting events the Aquarium hosts in advance, such as overnight stays and cocktails with the whales, before making travel arrangements to the aquarium.


    First off, there is a Main Street that is as traditional as they come, lined with mouthwatering restaurants, chic shops, and an abundance of art galleries. A renowned theater is also present, which is a perfect addition to the developing arts and culture scene. Beyond that, Chester offers a variety of hiking and walking opportunities right on the Connecticut River, so anyone who loves being outside will love it too! Here, you can easily plan the ideal romantic getaway or take a trip outside the city to get some much-needed rest and relaxation. Visit Chester, Connecticut to discover for yourself why it is such a unique and historically fascinating small town on the east coast.

    Photo by  Ebun Oluwole on Unsplash
    Photo by Ebun Oluwole on Unsplash
    Photo by Ebun Oluwole on Unsplash
    Photo by Ebun Oluwole on Unsplash
  3. Despite having a population of only 2,305, the natural beauty and historic charm of Chaplin, Connecticut, are unmatched. You'll enjoy strolling through the charming historic district, exploring the peaceful hiking trails, and soaking up the relaxed pace of life. The Connecticut town of Chaplin exudes a timeless New England charm. This adorable little town, founded in the 18th century, is full of historical artifacts. Benjamin Chaplin, who passed away in 1795 and left money to build a church close to his former home, is credited with giving the town its name. Spend some time exploring the Chaplin Historic District before venturing into the nearby wilderness.


    Beautiful structures like the former William Ross Public Library can be found as you stroll through these calm streets. It was founded in 1828 when the Goodell Lincoln General Store first opened. Visit the Chaplin Museum at 1 Chaplin Street if you enjoy history. Despite its diminutive size, this unusual location is packed with information. Take a stroll on the Two Sisters Trail for a peaceful and simple hike. This 1.3-mile hiking trail meanders through thick forests, giving you the impression that you are far from civilization. Without going to Diana's Pool, a trip to Chaplin isn't complete. Nothing beats a cooling swim in the ocean when it's hot outside. Naturally, this region is beautiful all year round. You'll be welcomed by exceptional foliage in the fall. The Natchaug River sparkles with frosted beauty in the winter. Go to the sleepy Connecticut town of Chaplin if you need some quiet time.

    Photo by 12019 on Pixabay
    Photo by 12019 on Pixabay
    Photo by 12019 on Pixabay
    Photo by 12019 on Pixabay
  4. Top 4

    Kent

    This Connecticut town is without a doubt the most picturesque there is! There is only one town that consistently wins the title of "Top Foliage Town in New England", and that town is Kent, despite the fact that it is difficult to compete with places like Cornwall and Essex. Your first impression of Kent will be its colonial vibe, which extends to the design of the buildings themselves. Not just the Historical Society, either. Not to mention that Kent Falls State Park, a local favorite, is nearby. This park is a must-see because of its distinctive collection of cascades. Here, there are more than 15 waterfalls to be found.


    People enjoy taking entire weekends to explore the acres of breathtaking natural beauty, as each one varies in height and shape. If you like to shop, you'll also find lots of unique stores and boutiques. Interesting statues and other art installations can be found all over the city. It resembles a live art exhibit. Additionally, the town comes alive in the fall with vivid hues you won't find anywhere else. You can cross the Housatonic River on the lovely Bull's Bridge on your way to explore the neighborhood. Washington once carried out the same action. If you decide that a single day simply isn't enough, reserve a room at the Inn at Kent Falls to get a closer look at the charm of the small town.

    Photo by 12019 on Pixabay
    Photo by 12019 on Pixabay
    Photo by 12019 on Pixabay
    Photo by 12019 on Pixabay
  5. Scenic Westport is situated on Connecticut's Gold Coast, a prime waterfront area, just 50 miles outside of New York City. A newly renovated library and the outdoor Levitt Pavilion, which hosts free (and occasionally fee-based) concerts in the summer, are also located in the thriving downtown area along the Saugatuck River. If you have been to Westport, Connecticut, you are aware that it is a wealthy area with a thriving cultural scene. Eccentric is the only adjective that adequately captures the marriage of luxury and traditional New England design. But it's that distinct charm that draws people back time and time again. Even without the trolley, the town has kept up its tradition of shopping, right down to the vibrant buildings.


    As far as the eye can see, the downtown of the town is packed with eateries and retail establishments that extend over hills and around corners. This town is everything you could hope for in a day trip destination: colorful brick and stone structures, boutiques stacked on top of one another. Although the interiors have changed, the majority of the old buildings are still standing. This thriving neighborhood is well-liked and frequently recommended as a must-see New England town. The monopoly it has created on the river, however, is its most peculiar characteristic. Here, you'll frequently find painters drawn by the red, blue, and green brick buildings that house some delectable dining options.

    Photo by Lo on Unsplash
    Photo by Lo on Unsplash
    Photo by Julia Sullivan on Unsplash
    Photo by Julia Sullivan on Unsplash
  6. A charming town called New Canaan can be found in Fairfield County, just 20 minutes from Stamford and an hour from New York City. New Canaan, another haven for commuters, has a downtown area that is much larger than the Main Streets in the other small towns on this list because it is so charming. The majority of the upscale stores, cafés, and eateries are located on Elm Street. The prices should reflect the clientele since this is a very wealthy town. Children can find ice cream shops in abundance.


    The renowned Glass House is New Canaan's top tourist destination. This eclectic residence, which was created and lived in by architect Philip Johnson, is among the most interesting homes you'll ever see and one of the best places to visit in Connecticut. You will be talking about it for years to come because it is so fascinating and special. Plan accordingly as it is only open from mid-April to mid-November. It is worthwhile to stop by the Silvermine Arts Center, especially to explore the area that bears the same name. It's like strolling through a postcard, this picture-perfect part of town. This region truly has it all: babbling brooks, old houses, white picket fences, and waterfalls. One of the most well-liked lodging options in the area is The Inn at GrayBarns. It is stunning, cozy, and home to a tavern where hungry patrons can enjoy delectable fare.

    Photo by Jeffrey Blum on Unsplash
    Photo by Jeffrey Blum on Unsplash
    Photo by 12019 on Pixabay
    Photo by 12019 on Pixabay
  7. The town of Fairfield is located in Connecticut's Fairfield County. Along Connecticut's Gold Coast, it shares a border with Bridgeport as well as the communities of Trumbull, Easton, Weston, and Westport. There are many distinct neighborhoods in Fairfield. The most well-known ones are affluent Southport, where former General Electric CEO Jack Welch resided for a number of years, and Greenfield Hill, with its sizable green spaces, renowned dogwood trees, and picturesque green home to a Congregational church with white spires.


    On Connecticut's Gold Coast, a charming small town is peacefully located. This lovely location, Fairfield, has five soft, sand beaches, tons of charm, and all the top-notch amenities you could ask for in a weekend getaway. You can choose from the beaches at Jennings, Penfield, South Pine Creek, Southport, and Sasco to lay out your towel, go swimming in the Long Island Sound, or have a picnic.


    Fairfield, one of the best beach towns in the state, is located between Bridgeport and Stamford and welcomes visitors who like to spend time taking in the charm of the Old Post Road Historic District, the fun of the outdoor Fairfield Farmer's Market, and the history of the Fairfield Museum and History Center. Wooden walkways are all over the Connecticut Audubon Society Birdcraft Museum and Sanctuary, which also has a lot of interesting birds on display. Don't skip a trip to Lake Mohegan Recreational Area if you're traveling with a four-legged friend. One of the best dog walking areas in Fairfield County, it also has a charming beach that's great for families in the warmer months.

    Photo by Adam Nemeroff  on Unsplash
    Photo by Adam Nemeroff on Unsplash
    Photo by Adam Nemeroff  on Unsplash
    Photo by Adam Nemeroff on Unsplash
  8. Old Saybrook is one of the oldest towns in Connecticut. It was founded in 1635 and is situated where the Connecticut River meets Long Island Sound. Many people recognize it as the former residence of the actress Katherine Hepburn. The main draw in the region is the Cultural Arts Center, which bears her name. Locals refer to it as "the Kate". On a peninsula with a view of Long Island Sound, Hepburn's former home is surrounded by other opulent homes and the most adorable private golf course you'll ever see. A beautiful stroll out to the lighthouse, also known as Lynde Point, is highly recommended in the area.


    The former Florence Griswold House has been transformed into a museum with a view of the sparkling Lieutenant River. The Robert and Nancy Krieble Gallery, a contemporary art space, is located behind the museum. There are some fantastic restaurants in the city, many of which serve regional seafood. Antiques and vintage items are sold in small shops, many of which line the charming Main Street. Hike through Rocky Neck State Park to reconnect with nature. You should pack plenty of snacks and water because this hidden gem is worth spending hours exploring. Another popular beach with tourists is Harvey's Beach, which is well-known for its calm, shallow water and tidy, soft sand.

    Photo by  Rusty Watson on Unsplash
    Photo by Rusty Watson on Unsplash
    Photo by Bill Burke on Unsplash
    Photo by Bill Burke on Unsplash
  9. Milford is a good option for visitors looking for an authentic Connecticut seaside town. Its charming character is difficult to match, and it is less crowded and touristy than many of the other beach towns in the state's southern region. When most people think of Christmas, they don't typically think of the coast, but it would be incorrect to discount places like Milford. In the winter, this waterfront city comes to life. Even in the dead of winter, people frequent Gulf Beach's pier, probably drawn by the breathtaking scenery. With a cup of the local coffee, you can endure this fascinating place even in the chilly winter. Visitors come here all year long for the downtown area, which offers fantastic shopping opportunities. But this place really comes alive during the Christmas season.


    The downtown area is enchanted by the lights on the green during the winter thanks to a 50-year-old custom. These locals genuinely enjoy the holiday season and aren't shy about expressing it. During the month of December, a house that goes by the moniker "That House In Milford" turns on its lights every evening at 5 o'clock. Combined with the festive downtown area, you could spend an entire weekend in this city!


    The old town still has many historical structures that have been converted into cafes, boutiques, and shops. One of the state's largest town greens, the inviting area is ideal for picnics and reading al fresco. Walnut Beach has one of the state's longest boardwalks, which also provides access for people with disabilities, and the beachfront offers rentals for enjoying the sand and surf. A well-known 297-acre area on the Sound with dunes and marshes is called Silver Sands State Park.

    Photo by Clay Banks on Unsplash
    Photo by Clay Banks on Unsplash
    Photo by Yana Ivanov on Unsplash
    Photo by Yana Ivanov on Unsplash



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