Oak Bluffs, Martha's Vineyard.

13 Most Underrated Towns In Massachusetts To Take A Trip To

Massachusetts is a moderately sized state in the northeastern United States. The state is one of the most well-known parts of New England, touches the Atlantic Ocean to the east, and borders several states, including Vermont, Rhode Island, Connecticut, New Hampshire, and New York. The state’s most famous city is its capital, Boston. Boston is home to famous historical events, like the Boston Massacre and the Boston Tea Party, but it is not the only city in Massachusetts that is worth taking a trip to while visiting. 

The whole state is steeped in history, culture, and natural beauty. Many of the smaller towns and underrated spots in the state hide unique spots like the site of the first recorded UFO sighting in the U.S.A. or the homes and retreat centers of famous authors, including Louisa May Alcott. Anyone hoping to get in touch with the lesser-known parts of Massachusetts should consider visiting the often-overlooked small towns dotting its beautiful landscape. 


The Town of Sheffield in Berkshire County, Massachusetts. Editorial credit: Richard Cavalleri / Shutterstock.com
The Town of Sheffield in Berkshire County, Massachusetts. Editorial credit: Richard Cavalleri / Shutterstock.com

Sheffield is the oldest town in Berkshire County, located in southern Massachusetts along the border of Connecticut. The English purchased the land, which later became Sheffield, from the native Stockbridge tribe in 1724. However, the first settler, Matthew Noble, didn’t arrive in the region until the fall of 1725. Those with a particular love of local historical sites will love Sheffield. The Ashley House and the Captain Truman Wheeler House are the top historic locations in and near town. 

The Ashley House dates back to its construction in 1735 by the young Colonel John Ashley, making it the oldest house still standing in Berkshire County. Although John Ashley was a staunch supporter of the Revolutionary War, it was the eventual liberation of the person he had enslaved, Elizabeth Freeman, that is the primary story tied to the site. The Captain Truman Wheeler House stands just outside the borders of Sheffield to the north of town and goes back to its construction in 1771. This home preserves many original features of the old home, including the original window sashes, meaning it's perfect for seeing how the wealthy of Massachusetts once lived their lives. Sheffield isn’t just ideal for enjoying fascinating historical spots, though. Many nearby parks, hiking trails, and a unique UFO site exist.  

UFO Park stands near the Housatonic River on Covered Bridge Lane. The covered bridge takes travelers over the river, but it's also close to the site of the first "historically true" UFO sighting in the United States. Although, alien and UFO sites aren’t for everyone. Fortunately, gorgeous and peaceful nature sites in and around town bring tourists a quiet experience immersed in nature. Bartholomew's Cobble Reservation is a beautiful outcropping of rock in the south of town and is an excellent spot for a leisurely stroll. Or, for those seeking something more intense, there is the Appalachian Trail, located near the lovely Three Mile Pond Wildlife Management Area. 


The public Clapp Memorial Library in Belchertown, MA. Editorial credit: Emma'sPhotos / Shutterstock.com
The public Clapp Memorial Library in Belchertown, MA. Editorial credit: Emma'sPhotos / Shutterstock.com

Belchertown sits along the Quabbin Reservoir, approximately an hour and a half east of Sheffield. The community received its unique name from Jonathan Belcher, the first royal governor of the region, who governed between 1730 and 1741. However, before European settlers came to the state, the area around Quabbin Reservoir was primarily used by native tribes for fishing and hunting, with permanent settlements set up near the Connecticut River. The Belchertown Historical Society is the best place to explore the town’s fantastic past. The Stone House, which serves as the meeting place for the historical society, dates back to 1827 and is a good example of the community’s early architecture. 

Although the historical society offers more than just a great glimpse into the past. The historical society also hosts events, like an ice cream social and lectures, and stores some artifacts from the region's early years, including Doctor Estes Howe’s Revolutionary War Notebooks. The town also boasts some stunning nature locations, like the Quabbin Reservoir site near the south of town or the Mount Holyoke Range State Park just outside the town’s borders. Mount Holyoke Range State Park consists of over 30 miles of walking trails through the rocky and wooded terrain of the area. It’s an idyllic spot for an exciting time outdoors, exploring all the Massachusetts landscape offers. 

The Quabbin Reservoir is another popular spot for outdoor-loving explorers who are sure to enjoy boating, hiking, and fishing along the shores of the 412 billion-gallon reservoir. Although there are some access limitations during winter, it is still a good spot for sightseeing. Whether tourists plan to visit in the winter or summer, the Suite at Liberty Woods will not disappoint. This cute little Airbnb sits on a 65-acre horse farm and provides the loveliest backdrop for a relaxing and rejuvenating vacation. The hosts also offer horsemanship, meditation, and yoga for those who wish to further enhance their restful break away from work.  


Petersham Common Historic District. In Wikipedia. https://en.wikipedia.org/wiki/Petersham_Common_Historic_District By Daderot - Own work, CC0, https://commons.wikimedia.org/w/index.php?curid=29952888
Petersham Common Historic District. In Wikipedia. By Daderot - Own work, CC0, Wikipedia

Petersham is only a forty-minute drive from Belchertown, located on the east of the Quabbin Reservoir. Petersham underwent several name changes over the years, with settlers originally naming the region Nichewaug after the native word for “the land between.” European settlers later changed the name to Volunteerstown or Voluntown but settled on the name of Petersham in 1754, likely naming the area after Petersham, England. 

However, the native name of Nichewaug remains memorialized in a small village by the native name located near the southern parts of Petersham. While a historically significant community, there are not many historical sites to see outside of some old buildings in the Petersham Common Historic District.

There are also plenty of gorgeous nature sites to explore, including hiking trails in nature preserves. The Quabbin Reservoir via Gate 40 is a fully immersive nature experience situated near Nichewaug Village and Petersham Road. It's an 8.2-mile trail that typically takes less than three hours to complete and is ideal for walking, hiking, mountain biking, and much more. Or, adventurous visitors can spend the weekend exploring the Petersham State Forest, a 3,500-acre forest perfect for bird watching and enjoying the state's natural beauty. Clamber Hill Inn is a lovely place to spend time away and rejuvenate after exploring the gorgeous town. Rest and relax in their outdoor spaces, dine at their high-class restaurant, and fall asleep in one of their cozy and welcoming rooms, some of which include a working fireplace. 


The gazebo in the apple orchard of Sholan Farms in Leominster, Massachusetts.
The gazebo in the apple orchard of Sholan Farms in Leominster, Massachusetts.

Leominster is commonly called the Pioneer Plastic City, thanks to its legacy as the inventor of modern injection moldings. Its reputation as an innovative city began long before the turn of the 20th century. Obadia Hills, a local resident, started manufacturing combs in 1775, which quickly became the region’s main industry. However, the lovely town isn’t just known for its industrial innovation; it is a naturally beautiful region with forests, lakes, and exciting adventure-themed activities. 

Some of the prettiest little lakes near and within the area are Whalom Lake, Notown Reservoir, Lake Shirley, and Spectacle Pond. While each of these bodies of water is worth checking out while in town, it is Lake Shirley, located just a few minutes east of the town’s borders, that has the most to offer. Shady Point Beach and Campground sits along the lake and is a great spot for summer and spring vacationers hoping to spend a few days outdoors indulging in the lake and its surrounding woodlands. Not only can guests rent a campsite and hike the paths in the woods, but the lake is also a popular place for boating and jet skiing. 

Other excellent seasonal spots to visit are the Leominster National Forest and Nashua Valley Conservation Area. The Nashua Valley Conservation Area is perfect for hiking, with Mount Elam being an excellent spot to get a good view of the landscape. Those planning a trip to town during the winter will be happy to learn that Leominster is located right alongside the Great Wolf Lodge of New England. The site's indoor water park means tourists will never have to worry about the weather when hoping to experience all the excitement this site offers. Not only does the Great Wolf Lodge offer endless fun for kids and adults alike, but it also has great rooms people can rent when planning a longer trip to Leominster.


Ski resort of Mount Wachusett on a sunny day in Westminster, Massachusetts. Editorial credit: Jay Yuan / Shutterstock.com
Ski resort of Mount Wachusett on a sunny day in Westminster, Massachusetts. Editorial credit: Jay Yuan / Shutterstock.com

Neighboring Leominster to the west is the community of Westminster, which sits near several stunning lakes, open spaces, and state parks. Fairbanks Moor was the very first European settler to arrive in the region in 1737, although the settlement didn’t officially become a town until October 20th, 1759. There are not many historical sites in town, but there are multiple parks like the Crocker Pond Recreation Area, which is perfect for a chill time enjoying the view of Crocker Pond and the nearby wildlife. While resting on a lawn chair and taking in the view is perfectly enjoyable, the more adventurous visitors will also appreciate canoeing on the open water and maybe even fishing.

Another fantastic outdoor excursion is the High Ridge Wildlife Management Area. This spot is a trendy place for anglers, hikers, cyclists, and lovers of local wildlife. It is home to local species of insects, as well as some local animals, including turkeys and deer. The place stretches for over 1,000 acres of primarily open fields, with views of two gorgeous nearby mountains, Mount Monadnock and Mount Wachusett. Westminster also hosts an amazing ski resort known as Wachusett Mountain, which shares its name with the town’s prominent peak. The resort is perfect for experienced skiers and beginners, with 27 total trails, eight ski lifts, and comfortable rooms where participants can recuperate and recharge for another day of skiing. 

Those who prefer a less intense sport should consider visiting the Woods of Westminster Golf Course. This site specializes in membership golfing but is not exclusive to members. Booking nine holes for a weekday costs $28.00, while booking eighteen holes costs $38.00 on a weekday. Guests can also add the lunch special to the 18-hole game for an extra $49.00.


Famous walkway to the dunes in Sandwich, Massachusetts. Editorial credit: Radomir Rezny / Shutterstock.com
Famous walkway to the dunes in Sandwich, Massachusetts. Editorial credit: Radomir Rezny / Shutterstock.com

Sandwich is located along Cape Cod Bay and north of Nantucket and Martha’s Vineyard. Being so close to such popular locations means that tourists venturing into the region often overlook Sandwich. However, Sandwich has lots of fascinating tourist attractions and an amazing history. The town’s European history began in 1637 when Edmund Freeman started settlements in the area, with the first permanent settlement starting in 1639. Early settlers highly valued it because of its rich marshlands along the coast, which were perfect for growing salt hay for livestock, making the region a highly prized spot in Massachusetts’s early history. 

The community is in the process of completing its Museum of Natural History by blending several prominent research and historical centers, known currently as the Thorton W. Burgess Society. The Thorton W. Burgess Society gets its name from the popular American children’s book writer by the same name who wrote Peter Cottontail, Old Mother Westwind, and other notable titles. The author was born and raised in Sandwich and loved the region’s natural beauty and wildlife, leading to the creation of the museum and nature center. Visitors to the site can enjoy the stunning gardens, explore the Green Meadow Forest exhibit, partake in storytime, and stop by the old Ida Putnam Jam Kitchen.

Those who enjoy the natural charm of the Thorton W. Burgess Society will probably enjoy the Myles Standish State Forest, which is just a few miles outside the town’s borders. The park offers camping, swimming, boating, and hiking along its many trails. Some of the trails are more rugged than others and better suited for young adults or those who aren’t traveling with the elderly and young children. Camping at this spot is a lot of fun. But for those who prefer a luxury experience or plan a trip in the winter, The Earl of Sandwich Motel is one of the finest spots to book a few nights. They have Standard Queen and Double rooms, which all boast elegant interior designs that help create a thoroughly restful and tranquil environment. Each room has comfortable beds, flat-screen TVs, and lots more for an affordable price. It is also conveniently located next door to the Old Sandwich Game Farm Wildlife Management Area, which is a gorgeous place to explore. However, be careful of wandering into the marsh areas since those are reserved for hunting during hunting times. 

Oak Bluffs

East Chop Light Oak Bluffs Martha's Vineyard Massachusetts.
East Chop Light Oak Bluffs Martha's Vineyard Massachusetts.

South of Sandwich, on the island of Martha’s Vinyard, is the beautiful and historical town of Oak Bluffs. Although not officially incorporated until 1907, Oak Bluffs shared much of its earlier history with Edgartown before it split from this community. This means Oak Bluffs shares its history with the oldest town on Martha’s Vinyard, which dates back to 1642. However, it was not until around the turn of the 20th century that people started to recognize this area’s potential as a seasonal tourist destination.

Visitors to the town can get a glimpse of some of the original tourist attractions when visiting places like the Flying Horses Carousel. This is the oldest platform carousel still in use in the country. It’s a very charming spot and represents Oak Bluffs’ early years as a resort community, and it is not the only historic place in town. Martha's Vineyard Camp Meeting Association is an adorable museum that showcases an authentic immersion into Oak Bluffs’ past, with vintage furniture, photos, and other unique features that make the campground feel like a true 1800s experience. The museum also has a great gift shop where tourists can get a souvenir for the road. 

Farm Neck Golf Course is the finest course in town that allows guests to book time on their courses, so there is no need to worry about holding a membership. Or, for those who prefer a faster-paced sport, Farm Neck also has tennis courts people can rent for a game or two. They also have a spectacular cafe and dining room at their restaurant, which makes for a whole-day event for those who like spending time actively outdoors and then indulging themselves in high-quality food and drink. The Narragansett House is an idyllic location to stay, as well as a historic place worth checking out. The stunning home dates back to 1870, and the rooms are a picturesque place to kick back and relax. 


Aerial Shoreline, Duxbury, MA.
Aerial Shoreline, Duxbury, MA.

Duxbury sits about thirty minutes north of Sandwich and south of Boston along the Atlantic coast. Although not as well known as its neighbor community, Plymouth, Duxbury, is one of Cape Cod Bay's most unique historical towns. Duxbury’s history goes back over 12,000 years, with native tribes calling the region home for centuries, particularly the Wampanoags residing in the area at the time of the arrival of European settlers in 1620. Before gaining the name of Duxbury, the town was known as Mattakeesett by the native peoples, a name which means “place of many fish.” This name reflects the community’s reputation as an abundant spot for fish and other sea creatures, which it still holds to this day. 

The town even has a seaside school, known as the Duxbury Bay Maritime School, that specializes in teaching children about marine wildlife. Although the school operates through registration, it also hosts community events, which guests can check out on the school’s website via the events tab. This year, they hosted a screening of the environmental film “Entangled.” The Duxbury Rural and Historical Society is responsible for preserving the town's cultural heritage. Some of the best sites to check out include the King Ceasar House, Bradford House, Nathaniel Winsor Jr. House, and Drew Archival Library. However, they also preserve cultural lands and landmarks, like the Second Meeting House Lot and Spar Soak. 

The King Caesar House dates back to 1809 and is a fantastically well-preserved early home of one of Duxbury’s pre-eminent shipbuilders, Ezra Weston II. Guests visiting the town can book a tour to see and learn all about the charming location on the historical society’s website. Another spot worth checking out is the Myles Standish Monument State Reservation. This spot celebrates one of the region’s founding members and is a gorgeous nature site with beautiful views of the surrounding ocean and landscapes. Those planning to stay a few nights can book a few nights at one of the many inns and hotels in the neighboring town of Plymouth. Hotel 1620 is by far the best spot to book a stay, offering stunning rooms like the Harbor View Suite and Poolview Suite. 


Newburyport historic downtown including State Street.
Newburyport historic downtown including State Street.

Newburyport is a lovely coastal town located an hour and a half north of Duxbury and a few miles south of the border of New Hampshire. It is a beautiful community that is the ideal quiet spot for those hoping to visit Boston but also spend time exploring a small town and appreciating the slower-paced experience. The town traces its history back to before the arrival of Europeans in 1635, originally inhabited by the Pawtucket Native tribe. Newburyport was once part of the settlement of Newberry Plantation until 1764, and in 1811, much of the town’s infrastructure was lost due to a massive fire leading to upgrades in the town’s fire and building code. 

Despite the fire, the city worked hard to rebuild its hometown, and there are many historical landmarks across the landscape that are well worth visiting. Some of the most notable include the old firehouse, the Spencer-Peirce-Little Farm, the Museum of Old Newbury, and the Swett Ilsley House. The firehouse dates back to its construction in roughly 1823 and served as a vital piece of the town’s culture since it housed the local market house and lyceum. Visitors can visit the arts center and enjoy music and plays at the same site that once hosted people like Ralph Waldo Emerson and Oliver Wendell Holmes. To see some of the old town artifacts housed and well-preserved in the Cushing House, one of the oldest homes in the community. 

Those hoping for a classy time in this underrated Massachusetts town will not be disappointed. There are dozens of wonderful cafes, restaurants, and other sites with exquisite cuisine and drinks that people of all ages will love. Some of the best spots include Mission Oak Grill, which is a great place for steak and drinks, and the Newburyport Brewing Company, where guests can get some freshly brewed drinks made locally. The Essex Street Inn is a great place to stay for anyone planning to visit Newburyport for more than a day (which is recommended since there is so much to see here). The Essex Street Inn has 37 stunning rooms for rent, which include luxurious private baths and cozy rooms that are wonderful for rejuvenation. 


Essex Salt Marsh - an original farm house adds to the beauty of the salt marsh in Essex, Massachusetts.
Essex Salt Marsh - an original farmhouse adds to the beauty of the salt marsh in Essex, Massachusetts.

Essex sits about thirty minutes south of Newburyport, touches the Atlantic Ocean to the east, and is a neighbor of the historic town of Ipswitch. Essex’s history began long before its official incorporation in 1819, with European settlers arriving there in 1679. At this time, the community bore the name of Chebacco and was part of the larger community of Ipswitch. In 1819, the community was forbidden from building a local meeting house; however, the women of Chebacco exploited a unique legal loophole that specified that no man of Chebacco could build a meeting house. Therefore, the women of Chebacco and several men from out of town chose to build the first meeting house in Essex in defiance of the authorities. 

The people take a lot of pride in their heritage, with many well-preserved historical buildings and sites that offer great views of the city’s past. Some of the most notable, many of which date back to the 17th and 18th centuries, include the Cogswell’s Grant and the Hearse House. The Cogswell’s Grant is a charming farmhouse along the Essex River that was originally built back in 1728, but when the Littles family purchased it in 1937, they set about rebuilding and restoring the old structure. The Hearse House, which is part of the property of the early congregation church, is a bit darker since it sits within the Old Graveyard of Essex, which experienced a series of grave robberies in the 1800s.

Visitors who prefer a more natural view will love Clam House Landing and the Allyn Cox Reservation. Clam House Landing rests along the Essex River and was a popular place for clam harvesting for native tribes before European settlers ever arrived. Settlers created an early salt marsh farm in 1648, raising dairy cattle and growing apples on a local orchard. This farm has existed for over 350 years, although today, it is more of a cultural highlight and nature site. Trekkers can traverse the nearby trail that showcases the local flora and fauna. After a long day outdoors, seeing all the town offers, guests should consider checking in at the local Cedar Hill Farm and Bed and Breakfast. The farmhouse is over 300 years old and is the perfect opportunity for tourists to immerse themselves in the early times of the community. 


The Orchard House, historic home of Louisa May Alcott.
The Orchard House, the historic home of Louisa May Alcott.

Concord is approximately 45 minutes west of Essex, with the Concord River running through its borders. People first arrived in the region during or shortly after the last ice age. These people were primarily hunter-gatherer tribes who lived off the land and consumed local wildlife and vegetation. Native settlements were mainly concentrated in a few small areas of town when Europeans arrived in 1635. 

This community is ideal for guests seeking a blend of outdoor beauty and historical wonder. In and around Concord’s borders are several parks, forests, and historical landmarks, including Minute Man National Historical Park and the home of the author, Louisa May Alcott. The historical home of Louisa May Alcott allows guests to attend informally during hours of operation and explore the beautiful home of the talented writer of “Little Women.” Minute Man National Historical Park is an exciting spot for hiking and learning about the very first armed conflict of the Revolutionary War, which took place in this location all the way back in 1775. 

Or, for those who may have read the works of transcendentalist Henry David Thoreau, the town of Concord is also home to the author's cabin, which overlooks Walden Pond. There are also plenty of hiking trails that showcase the town’s charm, including the many trails through Wright Woods and the Hapgood Forest Loop. Anyone hoping for a unique dish to finish off the night should visit Karma, which offers a fantastic blend of Asian fusion and French cuisine. The Concord Colonial Inn is the most unique and luxurious spot for travelers to recover. Not only will visitors enjoy top-notch lodging in a tranquil location, but they’ll also stay in one of Concord’s historical sites, dating back to 1716. 


Wharf look down on Rockport Harbor in Massachusetts.
Wharf looks down on Rockport Harbor in Massachusetts.

Just under twenty minutes west of Essex, sitting along the Atlantic coast of Massachusets, is the gorgeous town of Rockport. Rockport’s history dates back long before the arrival of Europeans in 1690, with the Agawam Native Tribe calling the area home. While the first settlement occurred in 1690 when Richard Tarr established a home in Sandy Bay, the Reverend John Avery, and his family were actually the earliest settlers when they were stranded on an island known as Crackwood’s Ledge in 1635. As the name suggests, the bay surrounding Rockport is rather rocky, with several small islands off the coast that make for a stunning view and plenty to explore.

The most notable island is Straitsmouth Island, which sits just offshore. The island is home to a historic lighthouse and the Straitsmouth Island Wildlife Sanctuary. Just south of Straitsmouth Island is Thacher Island, which also boasts a wildlife sanctuary and a historical lighthouse. Both islands are accessible via the local Thacher Island launch which costs $40.00 for people visiting from out of town. Alternatively, more adventurous travelers can take their own boat or kayak to these small islands and dock them for a small fee. There are also plenty of awesome small parks and larger state parks in town and within the surrounding region that make for ideal day trips. 

The site of Halibut Point is the best spot for a hike or cycling ride in nature. There are also the sites of Pigeon Cove Wharf and Cathedral Rocks for those who enjoy viewing the shore and spotting some local wildlife. Or, check out Folly Cove in the north of town and get a bite to eat at The Lobster Pool, a local restaurant that prepares fresh seafood in an amazing environment. There are plenty of places to stay for those planning to stay a few days, with the Emerson Inn and Yankee Clipper Inn being two of the finest spots to spend in town. Both sites provide a luxurious stay in a historical location with wonderful views of the sea and the local community.


 A young family walks through the charming Cape Cod town of Chatham, Massachusetts. Editorial credit: James Kirkikis / Shutterstock.com
 A young family walks through the charming Cape Cod town of Chatham, Massachusetts. Editorial credit: James Kirkikis / Shutterstock.com

Chatham is an often overshadowed town located near Cape Cod Bay, just south of the more known town of Provincetown. It is one of the oldest towns in Massachusetts, with a deep native and colonial history. Before Europeans arrived in the region, the Monomoyicks called it their home, where they farmed, hunted, and fished. In 1606, Samuel de Champlain became the very first European in the area when he explored what would later become the town of Chatham on his journey inland. In 1637, William Nickerson became one of the first permanent settlers after purchasing the land from a native local and winning pending litigation in court with the Plymouth General Court 10-12 years after his purchase. 

Chatham is certainly most well-known for its many gorgeous naturescapes, including small islands just offshore. The island of Monomoy is the must-see off-shore spot, with a historical lighthouse and nature preserve. This island was once a peninsula attached to the mainland, but storms and continuous erosion eventually separated the island and made it what it is today. In addition to exploring the local lighthouse and nature preserve, guests should consider putting aside some time to hike the shoreline of the island. Moving back to the mainland, Chatham also has several great outdoor and commercial locations that make for an exciting visit. 

The Morris Island Loop Trail, which, despite its name, is not on an island, is a fun way to enjoy the town’s coastline. It is a relatively easy trail with no serious inclines and typically only takes around thirty minutes to finish. There are also lots of top-notch hotels and restaurants to add a little class and lavishness to a trip. Mac’s Chatham Fish and Lobster is a delicious spot to buy a fresh seafood dinner, including oysters, lobsters, and much more. While Chatham has lots of beautiful hotels, Pleasant Bay Village Resort is one of the finest, with a restful atmosphere that includes charming gardens and swimming pools. 

Traveling to Massachusetts is a great choice for a vacation, especially during the Spring or Fall seasons, since the landscape is stunning at these times of the year. However, many people overlook the Massachusetts shoreline, which is often overshadowed by beaches in different states. The ocean can be chilly up north, but planning a few days to visit the beaches of Massachusetts during the summer is a great way to get to splash in the water or tan on the pristine sandy coast. Some of the best beaches in Gloucester include Half Moon Beach and one of the many beaches in and around Boston and Lovells Island. 

No matter what a tourist seeks, whether it is a relaxing day at the beach or an adventurous day exploring state parks, Massachusetts has plenty to offer. The state has 48 state parks, many state forests, and many recognized and preserved historical and cultural sites, making for the perfect getaway filled with learning.


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