The Most Beautiful Town in Connecticut: Ranking the Gem of the Nutmeg State

Choose the town you think is the most beautiful!

Author: Gregor Krambs
Updated on Apr 11, 2024 06:28
Discover the hidden gems of Connecticut by participating in our latest ranking – "What is the most beautiful town in Connecticut?" From charming coastal villages to picturesque countryside towns, we've gathered the best of the best for you to explore and vote for your favorite. Immerse yourself in the rich history, stunning landscapes, and vibrant communities that make up this enchanting state. Be a part of the decision-making process and make your voice heard by voting for your top pick. Don't see your favorite town on the list? No worries! You can suggest a missing option and share the love for your cherished town. Join thousands of others in this exciting StrawPoll ranking and uncover the true beauty of Connecticut!

What Is the Most Beautiful Town in Connecticut?

  1. 1
    This charming coastal town is known for its historic seaport, quaint shops, and delicious seafood.
    Mystic is a charming coastal town located in the state of Connecticut, United States. It is known for its rich maritime history, picturesque landscapes, and unique New England charm. The town is a popular tourist destination, offering a perfect blend of historic sites, scenic beauty, and a vibrant community atmosphere.
    • Mystic Seaport Museum: A renowned maritime museum that features historic ships, exhibits, and demonstrations.
    • Mystic Aquarium: An impressive aquarium with a diverse range of marine life, including beluga whales and penguins.
    • Olde Mistick Village: A charming shopping village with over 40 unique shops, galleries, and restaurants.
    • Mystic Pizza: Made famous by the 1988 movie of the same name, this pizzeria offers delicious pizzas and a slice of movie history.
    • Mystic Drawbridge: A historic bascule bridge that is still operational and opens for passing boats.
  2. 2
    Another picturesque town located along the Connecticut River, Essex is home to beautifully preserved colonial homes and a thriving arts scene.
  3. 3
    This affluent town is known for its stunning homes, world-class shopping, and picturesque waterfront.
    Greenwich is a captivating district located in southeast London, known for its remarkable beauty and rich historical significance. It is situated on the banks of the River Thames and offers breathtaking views of the city skyline. The area is a UNESCO World Heritage site and is famous for its maritime heritage, stunning parkland, and architectural wonders.
    • Greenwich Mean Time: Greenwich is the birthplace of Greenwich Mean Time (GMT), a time system used as the basis for Coordinated Universal Time (UTC)
    • Royal Observatory: Greenwich is home to the Royal Observatory, which served as the center for astronomical research and navigation. It is here that the Prime Meridian of the world is located.
    • Cutty Sark: Cutty Sark is a famous clipper ship located in the heart of Greenwich. It is the world's last surviving tea clipper and now serves as a museum.
    • Greenwich Park: Greenwich Park is one of the largest green spaces in London and offers stunning panoramic views of the city. It is home to various wildlife, beautiful gardens, and the iconic Greenwich Meridian.
    • Old Royal Naval College: The Old Royal Naval College is an architectural masterpiece in Greenwich. It was designed by Sir Christopher Wren and boasts stunning Baroque-style buildings.
  4. 4
    Located in the scenic Litchfield Hills, this town is known for its charming New England architecture, numerous antique shops, and outdoor recreation opportunities.
    Litchfield is a picturesque town located in Litchfield County, Connecticut. Known for its charming New England architecture and well-preserved historic buildings, Litchfield exudes a timeless charm and a sense of old-world beauty. The town is surrounded by rolling hills and lush greenery, providing a stunning backdrop for its quaint streets and peaceful atmosphere.
    • Historic Buildings: Litchfield is home to many well-preserved historic buildings, including the Litchfield Historical Society and the Tapping Reeve House and Law School, which is the first law school in the United States.
    • Scenic Beauty: The town showcases breathtaking natural beauty, with its rolling hills, picturesque farms, and stunning views of the surrounding countryside.
    • Litchfield Green: The Litchfield Green is a central gathering place in the town, featuring a beautiful park with a bandstand where community events and concerts often take place.
    • Antique Shops: Litchfield is known for its delightful antique shops, offering a wide range of unique and timeless treasures for collectors and enthusiasts.
    • White Memorial Conservation Center: Nature lovers can explore the White Memorial Conservation Center, a 4,000-acre wildlife sanctuary with scenic trails, lakes, and diverse ecosystems.
  5. 5
    New Canaan
    Noroton · Public domain

    New Canaan

    Jonathan Ogden Armour
    This upscale town is known for its well-preserved mid-century modern architecture, beautiful parks, and high-end shopping.
    New Canaan is a charming town located in Fairfield County, Connecticut. Known for its picturesque landscapes and affluent community, it offers a perfect blend of natural beauty and architectural elegance. The town is renowned for its well-preserved colonial homes, modern architectural masterpieces, and lush green spaces.
    • Population: Approximately 20,000
    • Location: Fairfield County, Connecticut
    • Year Founded: 1801
    • Area: 22.5 square miles
    • Median Household Income: Over $200,000
  6. 6
    This coastal town boasts picturesque beaches, a lively downtown area, and a thriving arts scene.
    Westport is a picturesque coastal town in Connecticut known for its natural beauty and charming New England charm. Situated on the breathtaking Long Island Sound, Westport offers a unique mix of stunning landscapes, historic architecture, and vibrant cultural scene.
    • Location: Located on the Long Island Sound, approximately 50 miles northeast of New York City.
    • Natural Beauty: Westport is surrounded by pristine beaches, lush forests, and scenic waterfront areas, offering endless opportunities for outdoor activities such as boating, fishing, and hiking.
    • Historic Architecture: The town boasts a rich history displayed through its beautiful historic buildings and landmarks, including the renowned Saugatuck Congregational Church and the Kemper-Gunn House.
    • Arts and Culture: Westport is home to a thriving arts scene with numerous art galleries, theaters, and cultural institutions, such as the Westport Country Playhouse and the Westport Arts Center.
    • Vibrant Downtown: The downtown area of Westport features quaint boutiques, local eateries, and charming coffee shops, creating a lively atmosphere for residents and visitors alike.
  7. 7
    Old Saybrook
    Juliejules · CC BY 3.0
    Located on the Connecticut River and Long Island Sound, this town is known for its charming downtown area, historic homes, and scenic waterfront.
    Old Saybrook is a charming coastal town located in Middlesex County, Connecticut. It is known for its picturesque landscapes, historic architecture, and a vibrant community. With a rich history dating back to the 17th century, Old Saybrook offers visitors a unique blend of natural beauty and cultural heritage.
    • Location: Middlesex County, Connecticut
    • Population: Approximately 10,000 residents
    • Coastline: 13 miles of scenic shoreline along Long Island Sound
    • Historic Sites: Old Saybrook Historical Society, General William Hart House, and Fort Saybrook Monument Park
    • Cultural Events: Annual Shakespeare on the Sound performances and vibrant local arts scene
  8. 8
    This quaint town is known for its well-preserved colonial homes, charming downtown area, and beautiful beaches.
    Guilford is a charming town located on the Connecticut shoreline. Its picturesque New England atmosphere is characterized by tree-lined streets, historic buildings, and beautiful natural landscapes. The town's rich history, dating back to 1639, is reflected in its well-preserved colonial architecture and inviting town center.
    • Population: Approximately 22,000
    • Location: Located on the Connecticut shoreline
    • History: Founded in 1639
    • Architecture: Well-preserved colonial buildings
    • Scenic Beauty: Picturesque natural landscapes
  9. 9
    Located at the eastern end of Long Island Sound, this town is known for its historic seaport, charming downtown area, and beautiful beaches.
    Stonington is a charming coastal town located in southeastern Connecticut. Known for its picturesque New England charm, historical significance, and scenic views, it is considered one of the most beautiful towns in the state.
    • Location: Stonington is situated on a peninsula between the Mystic River and Quiambaug Cove, offering stunning waterfront vistas.
    • Historical Significance: The town is home to numerous well-preserved colonial buildings, including the Old Lighthouse Museum and Stonington Harbor Light, which dates back to 1823.
    • Quaint Village Center: Stonington Borough, the town's village center, is listed on the National Register of Historic Places and features charming shops, galleries, and restaurants.
    • Coastal Scenery: The town boasts breathtaking views of Long Island Sound, with several scenic beaches and coastal trails for residents and visitors to enjoy.
    • Maritime Heritage: Stonington has a rich maritime history, with shipbuilding, fishing, and sailing playing integral roles in its past.
  10. 10
    This idyllic town is known for its well-preserved colonial homes, lively arts scene, and beautiful parks.
    Ridgefield is a picturesque town located in Fairfield County, Connecticut. Known for its charming streets lined with historic homes and vibrant downtown area, Ridgefield offers a unique blend of small-town charm and modern amenities. The town is nestled among rolling hills, providing breathtaking views of the surrounding countryside.
    • Population: Approximately 24,638
    • Area: Approximately 35 square miles
    • Location: Fairfield County, Connecticut
    • Distance from New York City: Approximately 55 miles
    • Historic Sites: Keeler Tavern Museum, Weir Farm National Historic Site

Missing your favorite town?


Ranking factors for beautiful town

  1. Natural beauty
    This includes the natural surroundings of the town, such as parks, forests, lakes, rivers, beaches, and scenic landscapes that attract visitors and make the town picturesque.
  2. Historic and architectural charm
    A beautiful town should have a rich history and well-preserved historic buildings and structures, such as historic homes, museums, churches, and public buildings. The architectural style of the town should also be considered, with a mix of well-maintained older and new buildings.
  3. Walkability and pedestrian-friendly streets
    A beautiful town should be easily navigable on foot, with clean, well-lit, wide sidewalks, crosswalks, and pedestrian-friendly areas that encourage residents and visitors to walk around and enjoy the town's beauty.
  4. Vibrant downtown and commercial areas
    A beautiful town should have a thriving downtown area with a mix of shops, restaurants, cafes, and other amenities that create a lively and welcoming atmosphere.
  5. Green spaces and parks
    A beautiful town should have ample green spaces, such as parks, gardens, and recreational areas, where residents and visitors can relax and enjoy outdoor activities.
  6. Cleanliness and well-maintained infrastructure
    A beautiful town should be clean, with well-maintained streets, buildings, and public spaces that show pride in the town's appearance.
  7. Public art and cultural attractions
    A beautiful town should offer cultural and artistic attractions, such as art galleries, museums, and theaters, as well as public art installations that add visual interest to the town's streets and public spaces.
  8. Safe and welcoming community
    A beautiful town should have a low crime rate and a friendly, welcoming atmosphere for residents and visitors alike.
  9. Quality of life and amenities
    A beautiful town should offer a high quality of life for its residents, with access to good schools, healthcare, recreational facilities, and other amenities that contribute to the overall well-being of the community.
  10. Unique and distinctive character
    A beautiful town should have a unique and distinctive character that sets it apart from other towns and makes it memorable to visitors. This can be a combination of its history, architecture, natural beauty, and local culture.

About this ranking

This is a community-based ranking of the most beautiful town in Connecticut. We do our best to provide fair voting, but it is not intended to be exhaustive. So if you notice something or town is missing, feel free to help improve the ranking!


  • 159 votes
  • 10 ranked items

Movers & Shakers

Voting Rules

A participant may cast an up or down vote for each town once every 24 hours. The rank of each town is then calculated from the weighted sum of all up and down votes.

More information on most beautiful town in connecticut

Connecticut is a state that's rich in history and natural beauty. From picturesque coastal towns to charming inland communities, there are many contenders for the title of most beautiful town in the state. Connecticut's small size means that it's easy to explore multiple towns in a single day, making it an ideal destination for those seeking a scenic road trip. Whether you're looking for quaint New England architecture, stunning waterfront views, or lush greenery, Connecticut has it all. In this article, we'll take a closer look at some of the most beautiful towns in Connecticut, as voted on by our users here at StrawPoll.

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