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Best Small Towns in Massachusetts: Explore Outside Of Boston

Often, when people think about Massachusetts, they think of Boston. Of course, Boston is a great city, we’ve written many posts about it, including how to get around using public transportation and the best food options. Massachusetts is so much more than Boston. And sometimes, we just needed to get out of Boston and enjoy small-town life. Come with me as we explore some of the best small towns in Massachusetts.

  • Concord, MA
    • Walden Pond
    • Concord Museum
  • Manchester-By-The-Sea, MA
    • Manchester Music Festival
    • Manchester-by-the-Sea Film Festival
  • Marblehead, MA
    • Fort Sewall
    • Castle Rock Park
  • Lenox, MA
    • Tanglewood Music Festival
    • Lenox Village
  • Rockport, MA
    • Paper House
    • Bearskin Neck
  • Salem, MA
    • Salem Witch Museum
    • Peabody Essex Museum
  • Martha's Vineyard, MA
    • Gay Head Lighthouse
    • Joseph Sylvia State Beach
  • Conclusion: Small Towns in Massachusetts

We used the definition of a small town to be any town with less than a population of 25,000 people as of the last census. Many of these small towns have very connected residents and aren’t usually crowded with tourists. This means that you won’t spend a lot of time waiting in line. You won’t be overcharged for things as a tourist. And you’ll get to see the slower side of life and meet some of the most amazing people.

Concord, MA

Concord, MA is a beautiful and historic town located just 20 miles outside of Boston. It was the site of the first battle of the American Revolution, and is home to many important landmarks such as the Old North Bridge and the Concord Museum. We highly recommend taking a driving tour to explore the revolutionary history of the town. The town is also known for its picturesque scenery, with charming colonial homes and tree-lined streets. It’s a great place to visit for history buffs, nature lovers, or anyone looking for a peaceful escape from the hustle and bustle of city life. It’s also the first community in the United States to ban single-use plastic bottles.

Walden Pond

Walden Pond in Concord, MA is one of the most serene and peaceful places I have ever been to. It’s no wonder that it was the inspiration for Henry David Thoreau’s famous book, Walden. The calm blue waters and surrounding forest create a sense of tranquility that is hard to find in today’s fast-paced world. It’s the perfect spot for a quiet hike, a picnic, or just some quiet reflection. I highly recommend a visit to this beautiful natural wonder.

Concord Museum

The Concord Museum is a must-visit attraction for anyone interested in American history. The museum offers a fascinating glimpse into the town’s role in the Revolutionary War, as well as its literary and intellectual past. The museum’s collection includes artifacts such as Paul Revere’s lantern, Henry David Thoreau’s desk, and Ralph Waldo Emerson’s study. Visitors can also explore the museum’s extensive collection of American decorative arts, including furniture, ceramics, and silver. With knowledgeable staff and engaging exhibits, the Concord Museum is an ideal destination for history buffs and curious travelers alike.

A cup of Ice Cream from Bedford Farms in the small town of Concord, Massachusetts

Manchester-By-The-Sea, MA

Manchester-by-the-Sea, MA is a quaint coastal town located in Essex County. The town is known for its beautiful beaches, charming New England architecture, and historic landmarks. Visitors can stroll through the picturesque downtown area and enjoy shopping and dining at local businesses, or take a scenic drive along the coastline to take in the stunning views of the ocean. Manchester-by-the-Sea also has a rich cultural and artistic community, with events such as the Manchester Music Festival and the Manchester-by-the-Sea Film Festival. Overall, this charming town offers something for everyone and is definitely worth a visit.

Manchester Music Festival

The Manchester Music Festival in Manchester-by-the-Sea, MA is a must-visit event for all music lovers. This festival is a celebration of classical music, featuring some of the most talented musicians from around the world. The festival takes place in various locations throughout the town, including the beautiful Tucks Point and the stunning Manchester-Essex High School auditorium. The festival’s program is carefully curated each year to showcase a diverse range of music styles and performers. From solo piano recitals to full orchestral performances, there is something for everyone at the Manchester Music Festival. The festival also offers workshops and masterclasses for aspiring musicians, providing an opportunity to learn from some of the best in the industry. Attending the Manchester Music Festival is a truly unique experience.

Manchester-by-the-Sea Film Festival

The Manchester-by-the-Sea film festival is truly a fantastic experience. The festival showcases a diverse range of films, from heartwarming dramas to thought-provoking documentaries. The festival organizers did an outstanding job putting everything together. If you are a fan of film, I highly recommend attending the Manchester-by-the-Sea film festival.

Marblehead, MA

Marblehead, MA is a charming coastal small town located on the North Shore of Massachusetts. With its narrow streets and historic architecture, it is a popular destination for tourists and locals alike. The town is home to several beautiful beaches, including Devereux Beach and Marblehead Neck Beach, which offer stunning views of the Atlantic and are perfect for swimming, sunbathing, and beachcombing. Marblehead is also known for its rich history; the town has several museums and historic sites, including the Marblehead Museum and the Old Burial Hill Cemetery. Whether you’re interested in history, outdoor recreation, or just relaxing by the sea, Marblehead has something to offer everyone.

Fort Sewall

Fort Sewall was built in the early 1700s to defend against potential sea attacks. Today, Fort Sewall serves as a popular destination who come to enjoy the stunning views of the harbor and the ocean beyond. Visitors can explore the fort’s grounds and take in the area’s scenic beauty. Additionally you can simply relax and watch the boats sailing by. Whether you’re a history buff or just looking for a peaceful spot to take in some fresh sea air, Fort Sewall is definitely worth a visit. Admission is free.

Castle Rock Park

Visiting Castle Rock Park is such a beautiful experience! The park is surrounded by lush greenery and offers stunning views of the surrounding mountains. There are plenty of hiking trails to explore and the park is well-maintained and clean. I particularly enjoyed the scenic overlooks and the refreshing breeze that kept me cool during my hike. The park also has picnic areas and playgrounds, making it a great place to bring the whole family. Overall, Castle Rock Park is a must-visit destination for anyone who loves the outdoors and wants to experience the beauty of nature.

An image of the waterfront in Marblehead, MA

Lenox, MA

A charming small town located in the Berkshire Mountains of Western Massachusetts. It is known for its beautiful scenery, including the popular Tanglewood music festival venue and the historic Lenox Village. Visitors can enjoy a range of activities, such as hiking, skiing, and exploring the local boutiques and galleries. The town is also home to several notable restaurants and inns. It is a perfect destination for a weekend getaway or a longer vacation. Whether you’re looking for outdoor adventures or a cultural experience, Lenox has something for everyone.

Tanglewood Music Festival

The Tanglewood Music Festival is a must-visit event for music lovers. The festival showcases some of the best musicians and performers from around the world. The atmosphere is simply electric. The outdoor setting is perfect for enjoying live music, and the beautiful scenery adds to the overall experience. From classical to contemporary, there’s something for everyone at Tanglewood. The festival also offers a variety of food and beverage options. It is a great place to spend an entire day with friends and family. If you haven’t had the chance to attend the Tanglewood Music Festival, you’re missing out on an unforgettable experience.

Lenox Village

This picturesque village is known for its stunning natural beauty, quaint New England architecture, and rich cultural heritage. Visitors can explore the many art galleries, boutique shops, and restaurants that line the bustling streets. Visitor can also take a leisurely stroll through the town’s scenic parks and gardens. With its vibrant community of artists, musicians, and writers, Lenox Village offers a unique and inspiring atmosphere.

Rockport, MA

Rockport, MA is a charming coastal town located on the tip of Cape Ann. Known for its picturesque harbor and stunning beaches, Rockport is a popular destination for tourists and locals alike. The town is also home to a vibrant artist community, with numerous galleries and studios showcasing their work. Visitors can explore the historic district, where they will find beautiful homes and buildings dating back to the 18th and 19th centuries. Whether you’re looking to relax on the beach, enjoy some seafood, or browse unique shops and boutiques; Rockport has something for everyone.

Paper House

The Paper House in Rockport, MA is a unique and intriguing attraction that is worth checking out. The house is made entirely out of paper. Elis Stenman constructed this house in the 1920s. He used newspapers and other types of paper to build the interior and exterior walls, as well as the furniture inside. The paper house has stood the test of time and remains a popular tourist destination today. Visitors can take a guided tour of the house and learn about its history and construction. It’s truly remarkable to see how durable and sturdy paper can be when used in such a creative way.

Bearskin Neck

Bearskin Neck is a charming neighborhood in Rockport, MA that is definitely worth a visit. This area is famous for its unique shops, art galleries, and seafood restaurants. You can stroll along the narrow streets and admire the colorful buildings while enjoying the fresh sea air. One of the highlights of Bearskin Neck is the Rockport Motif Number 1. It is a red fishing shack that has been painted by many artists over the years. If you’re lucky, you might even spot a seal or two swimming in the harbor. Overall, Bearskin Neck is a lovely place to spend a relaxing afternoon exploring the local culture and scenery.

A cute little ice cream store in Rockport, MA - One of our favorite small towns in Massachusetts

Salem, MA

Salem, Massachusetts is a quaint and historic small town located on the North Shore of Massachusetts. Known for its infamous witch trials in the late 1600s, Salem has since become a popular tourist destination for those interested in the town’s dark history. Visitors can explore the Witch Trials Memorial, the Salem Witch Museum, and even take a haunted walking tour through the town’s spooky streets. In addition to its witch-related attractions, Salem also boasts beautiful architecture, delicious seafood restaurants, and scenic waterfront views. Whether you’re a history buff or simply looking for a charming New England getaway, Salem is a must-visit destination. We visited Salem a number of times and wrote an article about the spooky things that occur there.

Salem Witch Museum

The Salem Witch Museum is a fascinating destination for anyone interested in history and the paranormal. The museum provides visitors with an in-depth look into the infamous Salem witch trials of 1692, which resulted in the death of 20 innocent people. The exhibits are informative and captivating, featuring life-size dioramas and interactive displays that allow visitors to immerse themselves in the history of the trials. Additionally, the museum offers guided tours and educational programs for those who want to learn even more about the trials and the people involved.

Peabody Essex Museum

The museum is home to an impressive collection of art and artifacts from around the world, with a focus on the maritime history of New England. The museum’s galleries are beautifully curated and offer a unique and fascinating glimpse into the past. From intricate Chinese art to stunning ship models and everything in between, the Peabody Essex Museum is a true gem of the Salem community.

Salem for Halloween is a great small town to visit in Massachusetts
People dressed up in Salem for Halloween
Brooms in Salem for flying or sweeping

Martha’s Vineyard, MA

Martha’s Vineyard is a stunning island located off the coast of Massachusetts. Known for its beautiful beaches, quaint towns, and picturesque scenery. Martha’s Vineyard is a popular destination for tourists and locals alike. With a rich history dating back to the 1600s, the island is home to a number of historic sites, including the charming gingerbread houses in Oak Bluffs and the Gay Head Lighthouse in Aquinnah. Visitors can also enjoy a variety of outdoor activities, such as kayaking, hiking, and biking, or simply relax and take in the natural beauty of the island. Whether you’re looking for a peaceful retreat or an exciting adventure, Martha’s Vineyard is a small town in Massachusetts that has something for everyone.

Gay Head Lighthouse

Gay Head Lighthouse, also known as the Aquinnah Lighthouse, is a beautiful landmark located on the westernmost point of Martha’s Vineyard. The lighthouse was first built in 1799 and has since undergone several renovations and improvements to ensure its longevity. Known for its reddish-brown brick color, Aquinnah Lighthouse has stunning views of the Atlantic Ocean. Visitors can climb to the top of the lighthouse for an even more breathtaking view of the surrounding area. The Gay Head Lighthouse is a must-visit attraction for anyone visiting Martha’s Vineyard, and it serves as a reminder of the island’s rich history and culture.

Joseph Sylvia State Beach

Joseph Sylvia State Beach is one of the most beautiful beaches in Martha’s Vineyard, MA. It is located on the south side of the island. The beach is known for calm waters and soft, sandy shores. The beach stretches for miles, so there’s plenty of room for everyone to spread out and enjoy themselves. There are also plenty of amenities available, including restrooms, showers, and concession stands. Whether you’re looking to lounge in the sun, swim in the refreshing waters, or play a game of beach volleyball, Joseph Sylvia State Beach is the perfect place to do it all.

Conclusion: Small Towns in Massachusetts

Whether you want to walk along the beach, shop-lined streets, or the historic streets of the Revolutionary War, Massachusetts has some great options. Many of the little towns along Eastern Massachusetts are accessible by the MBTA Commuter Rail. Even if you’re starting in Boston, you can get to many cute little towns without a car. We would regularly hop on the train to get out of Boston and explore what’s nearby, and we strongly encourage you to do the same.

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Larry French
A picture of Daphne and I

Thanks for stopping by. We are Larry & Daphne French, the founders of Our French Travels. Our shared love of travel has led us to start sharing some of our adventures here. We are constantly on the lookout for our next adventure; so far we have visited over 70 cities worldwide with hundreds more on our bucket list. When we are not traveling or planning our next adventure, we can be found at home playing with our cat and dog. Learn more about us here.

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