The Most Beautiful Town in Massachusetts: Ranking Nature's Gem

Choose the town you think is the most beautiful!

Author: Gregor Krambs
Updated on Feb 17, 2024 05:28
Discover the charm and allure of Massachusetts' picturesque towns as we unveil the ultimate ranking of the most beautiful towns in the Bay State! At StrawPoll, we invite you to dive into a world of stunning landscapes, quaint village centers, and rich history as you cast your vote for your favorite town or suggest a hidden gem that deserves recognition. Thousands of polls and rankings on various topics await your opinion, and now it's time to make your voice heard in our quest to crown the most beautiful town in Massachusetts. So, what are you waiting for? Join the growing community of StrawPoll enthusiasts and let the beauty of Massachusetts sweep you off your feet!

What Is the Most Beautiful Town in Massachusetts?

  1. 1
    With its picturesque beaches, lighthouses, and historic architecture, Nantucket is a beautiful town that feels like stepping back in time.
    Nantucket is a picturesque island town located in Massachusetts, known for its charming cobblestone streets, historic buildings, and stunning natural beauty. Situated 30 miles south of Cape Cod, Nantucket boasts miles of pristine sandy beaches, dunes, and grassy landscapes. The town offers a unique blend of colonial grandeur and coastal allure, making it a popular destination for tourists and locals alike.
    • Location: Located in Nantucket County, Massachusetts.
    • Size: Nantucket covers an area of approximately 105 square miles.
    • Population: As of 2020, Nantucket had an estimated population of around 11,000 residents.
    • Architecture: The town features a rich architectural heritage, with many well-preserved historic homes and buildings, including Captain's mansions and quaint cottages.
    • Whaling History: Nantucket has a prominent whaling history, and its Whaling Museum attracts visitors with exhibits on the island's maritime traditions.
  2. 2
    Nestled in the Berkshires, Lenox is a charming town known for its elegant architecture, cultural attractions, and stunning natural scenery.
    Lenox is a picturesque town located in Berkshire County, Massachusetts. It is known for its stunning natural beauty, rich history, and thriving cultural scene. The town offers a perfect blend of charming New England architecture, scenic landscapes, and a vibrant community.
    • Location: Lenox is situated in Berkshire County, Massachusetts.
    • Natural Beauty: The town is surrounded by the scenic rolling hills of the Berkshire mountains.
    • Cultural Scene: Lenox is home to the renowned Tanglewood Music Center, the summer home of the Boston Symphony Orchestra.
    • Historical significance: Lenox is steeped in history with numerous historic landmarks and preserved buildings.
    • Lenox Village: The town center is marked by a charming village, complete with quaint shops, art galleries, and fine dining establishments.
  3. 3
    This historic town is known for its scenic beauty, charming downtown, and association with American literary giants like Ralph Waldo Emerson and Louisa May Alcott.
    Concord is a picturesque town located in Middlesex County, Massachusetts. It is known for its rich history, charming New England architecture, and natural beauty. The town is situated on the banks of the Concord River and is surrounded by rolling hills, lush forests, and serene landscapes. Concord has a small-town charm with a vibrant community and a strong sense of cultural and historical heritage. It offers a peaceful and idyllic setting for its residents and visitors alike.
    • Population: Approximately 18,000
    • Size: 25.9 square miles
    • Historical Significance: Concord played a crucial role in the American Revolutionary War, serving as the site of the Battle of Lexington and Concord.
    • Ralph Waldo Emerson: This renowned American essayist and poet called Concord his home and wrote many of his famous works here.
    • Henry David Thoreau: Famous for his book 'Walden,' Thoreau resided in a cabin near Walden Pond, located in Concord.
  4. 4
    With its rocky coastline, quaint fishing village vibe, and charming downtown, Rockport is a quintessential New England town.
    Rockport is a picturesque coastal town located in Essex County, Massachusetts. Known for its stunning natural beauty and charming New England atmosphere, Rockport attracts visitors with its scenic beaches, historic neighborhoods, and vibrant artist community. The town is situated on the Cape Ann peninsula and offers breathtaking views of the Atlantic Ocean.
    • Population: Approximately 7,000 residents
    • Location: Essex County, Massachusetts
    • Geography: Cape Ann peninsula, Atlantic Ocean coastline
    • Famous Landmarks: Bearskin Neck, Motif No. 1, Halibut Point State Park
    • Beaches: Front Beach, Back Beach, Long Beach
  5. 5
    This coastal town is known for its beautiful harbor, historic homes, and charming downtown filled with boutiques, galleries, and restaurants.
    Marblehead is a charming coastal town located in Essex County, Massachusetts. Known for its picturesque harbor, historic architecture, and scenic beauty, Marblehead offers visitors a glimpse into New England's rich maritime heritage. Its narrow streets, lined with well-preserved 18th and 19th-century homes, create an enchanting atmosphere that reflects the town's colonial past. Marblehead's idyllic coastal setting, pristine beaches, and thriving arts community further enhance its allure.
    • Location: Essex County, Massachusetts
    • Year Founded: 1629
    • Population: Approximately 20,000
    • Area: Approximately 4.4 square miles (11.4 km²)
    • Harbor: Famous for its scenic beauty and as a popular spot for sailing
  6. 6
    Another picturesque town in the Berkshires, Stockbridge is known for its beautiful architecture, cultural attractions, and stunning natural scenery.
    Stockbridge is a picturesque town located in Berkshire County, Massachusetts. Nestled in the heart of the Berkshires, it is renowned for its charming New England architecture, scenic beauty, and rich historical heritage. The town offers a peaceful and idyllic retreat, attracting visitors from all over the world.
    • Norman Rockwell Museum: Stockbridge is home to the iconic Norman Rockwell Museum, showcasing the works of the beloved American artist.
    • Berkshire Botanical Garden: The town boasts the beautiful Berkshire Botanical Garden, featuring diverse plant collections, serene walking trails, and educational programs.
    • The Red Lion Inn: The historic Red Lion Inn, established in 1773, offers a unique lodging experience with its old-world charm, warm hospitality, and award-winning cuisine.
    • Tanglewood Music Center: Stockbridge is located near the Tanglewood Music Center, the summer home of the Boston Symphony Orchestra, hosting world-class musical performances.
    • Stockbridge Bowl: The town features the stunning Stockbridge Bowl, a scenic lake offering opportunities for boating, swimming, and other water activities.
  7. 7
    Located on the island of Martha's Vineyard, Edgartown is a beautiful town known for its historic homes, charming downtown, and scenic harbor.
    Edgartown is a picturesque seaside town located on the island of Martha's Vineyard in Massachusetts. It is renowned for its historic charm, pristine beaches, and elegant architecture. As one of the most beautiful towns in Massachusetts, Edgartown exudes a timeless New England appeal.
    • Historic Charm: Edgartown is filled with beautifully preserved historic buildings, including grand homes, churches, and lighthouses.
    • Pristine Beaches: The town boasts scenic sandy beaches, such as South Beach and Joseph Sylvia State Beach, offering breathtaking ocean views.
    • Elegant Architecture: Edgartown's architecture showcases classic New England style, with white clapboard houses, picket fences, and beautifully manicured gardens.
    • Charming Main Street: The town's Main Street is lined with quaint shops, boutiques, art galleries, and delicious seafood restaurants.
    • Edgartown Harbor: The harbor is a bustling hub, where visitors can admire luxury yachts, go sailing, or embark on fishing charters.
  8. 8
    This coastal town on Cape Cod is known for its beautiful beaches, charming downtown, and historic lighthouse.
    Chatham is a charming coastal town located in Cape Cod, in the state of Massachusetts. It is known for its picturesque landscapes, peaceful beaches, and historic architecture. The town offers a perfect blend of natural beauty and small-town charm, making it one of the most beautiful towns in Massachusetts.
    • Location: Cape Cod, Massachusetts
    • Natural Beauty: Picturesque landscapes, peaceful beaches
    • Architectural Style: Historic buildings
    • Charm: Small-town charm
    • Coastline: Miles of coastline
  9. 9
    Home to Williams College and the Clark Art Institute, Williamstown is a beautiful town known for its cultural attractions, scenic beauty, and charming downtown.
    Williamstown is a picturesque town located in Berkshire County, Massachusetts. It is known for its stunning natural beauty, charming New England architecture, and vibrant cultural scene. The town offers residents and visitors a perfect blend of rural tranquility and urban amenities, making it an exceptionally enjoyable place to live or visit.
    • Population: Approximately 7,800 residents
    • Location: Berkshire County, western Massachusetts
    • Founded: 1765
    • Geography: Located in the Berkshire Mountains
    • Attractions: Williams College, Clark Art Institute, Williamstown Theatre Festival
  10. 10
    While technically not a town, Cambridge is a beautiful city known for its stunning architecture, rich history, and vibrant culture. Home to Harvard University and MIT, Cambridge is a hub of innovation and creativity.
    Cambridge is a picturesque city situated in the county of Cambridgeshire, England. Renowned for its prestigious university and stunning architecture, it boasts a rich history that dates back over 800 years. The city is known for its tranquil river, charming cobbled streets, and beautiful green spaces.
    • Population: approximately 130,000
    • University: University of Cambridge
    • Famous Colleges: King's College, Trinity College, St John's College
    • Architectural Marvels: King's College Chapel, Mathematical Bridge, Great St Mary's Church
    • River: The River Cam flows through the city, providing scenic views and opportunities for punting

Missing your favorite town?


Ranking factors for beautiful town

  1. Natural beauty
    Consider the town's surrounding landscape, such as scenic views, bodies of water, mountains, forests, and parks that add to the overall beauty of the town.
  2. Architecture and historic charm
    Take into account the town's architecture, including historic buildings, charming streets, and well-preserved landmarks that contribute to the unique character of the town.
  3. Vibrant downtown or main street
    A beautiful town should have a lively and inviting downtown or main street area, filled with locally owned shops, restaurants, galleries, and other attractions.
  4. Public spaces and community amenities
    Look for well-maintained parks, gardens, squares, or other public spaces that provide opportunities for relaxation and community events.
  5. Cleanliness and maintenance
    A town's overall cleanliness and maintenance plays a significant role in its beauty. Look for well-kept streets, buildings, and landscaping.
  6. Walkability and accessibility
    A beautiful town should be easy to explore on foot or by other means of transportation, with pedestrian-friendly streets and sidewalks, as well as good public transportation options.
  7. Activities and attractions
    A beautiful town should offer a diverse range of cultural, recreational, and entertainment options for residents and visitors.
  8. Community spirit and pride
    Look for a town where residents are actively involved in preserving and enhancing the local environment and heritage.
  9. Safety and low crime rates
    A town's crime rates and overall safety contribute to its beauty and appeal.
  10. Quality of life and overall atmosphere
    Consider the town's overall atmosphere, including factors such as education, employment, health care, housing, and cost of living, which contribute to residents' overall quality of life.

About this ranking

This is a community-based ranking of the most beautiful town in Massachusetts. 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!


  • 170 votes
  • 10 ranked items

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 massachusetts

Massachusetts is a state located in the northeastern region of the United States. It is known for its rich history, vibrant culture, and stunning natural beauty. Among the many attractions that Massachusetts has to offer, its towns stand out as some of the most beautiful and charming places to visit. The state is home to a diverse range of towns, each with its unique character and charm. From the quaint coastal towns of Cape Cod to the bustling college towns of Amherst and Northampton, Massachusetts has something to offer for everyone. When it comes to the most beautiful towns in Massachusetts, there are plenty of contenders. Some of the top picks include Nantucket, a charming island town known for its picturesque harbor and historic architecture, Concord, a historic town famous for its role in the American Revolution, and Lenox, a quaint town nestled in the heart of the Berkshires. Whether you're a history buff, a nature lover, or simply looking for a peaceful retreat, Massachusetts' beautiful towns are sure to captivate your heart and leave you with lasting memories.

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