Nantucket, Massachusetts/USA - August 9 2019: the Town of Nantucket is home to an eclectic range of shops including high end galleries, clothes shops, souvenir stores, a bookshop and a liquor store.

13 Prettiest Towns in Massachusetts

Many people think of Puritans, Pilgrims, and the Boston Red Sox when they hear about Massachussets. While these are all essential aspects of the state's history and culture, many small towns have breathtaking views and stunning landscapes. The views of the Atlantic Ocean, coupled with colonial-era architecture, make it a spectacular site for photography and relaxation. These thirteen towns have the best views, the loveliest wildlife sites, historical monuments, and so much more. 


Minuteman statue in Concord, Massachusetts.
Minuteman statue in Concord, Massachusetts.

Concord is a gorgeous community located a few miles west of Boston, rich in history and culture. Established in 1635, the history of this region reaches back over 10,000 years, with Native cultures using the waterways for food and transportation. The English were the first Europeans in the area, and Concord was their first inland settlement. 

Tourists can experience the fantastic history of the town through the more than a dozen historical sites preserved across town. Walk the grounds of the Ralph Waldo Emmerson house, the famous transcendental thinker of the 1800s and teacher of Thoreau. Explore the Old North Bridge, the famed location of the "shot heard round the world" during the Revolutionary War. These fantastic sites aren't the only stunning parts of Concord. The region boasts some of the loveliest natural scenery, especially in fall and early spring. Stop by Louisa May Alcott's Orchard House before visiting Concord Provisions and Country Kitchen to grab a bite to eat! 


The harbor at Concord, Massachusetts.
The harbor at Concord, Massachusetts.

While Concord is well known for its historical significance during the Revolutionary War, Rockport is better known for its gorgeous beaches and wild atmosphere. The community is welcoming and warm, so you're sure to make a friend or two while exploring all this area offers. 

The Agawam Indian tribe inhabited the region long before the arrival of the English in the early 1600s. At its founding, it was part of Gloucester, but residents later abandoned the settlement for approximately 100 years. In the 1800s, it split from Gloucester and became Rockport. Around this time, the granite quarries opened, bringing financial prosperity to the town. 

If you plan to stay in this lovely town for several days, then the Rockport Inn and Suites are ideal. They offer comfortable lodging, an indoor pool, and a continental breakfast in the heart of town. However, if you want a place closer to the gorgeous ocean views, check out the Seafarers Inn on the town's coastline!

Oak Bluffs 

Gingerbread cottages in Oak Bluffs, on Martha's Vineyard.
Gingerbread cottages in Oak Bluffs, on Martha's Vineyard. 

Oak Bluffs might not have the prettiest-sounding name, but it's a gorgeous resort town on Martha's Vinyard Island! It was once known as Cottage City in the late 1880s until it changed its name to reflect its transition to a more luxurious village. 

East Chop Lighthouse is a must-see attraction in this small island town. The lighthouse is an essential historical landmark with amazing views of the surrounding waters! The Oak Bluffs Town Beach is one of the prettiest in the area and is perfect for anyone hoping to get some sunshine. After a long day exploring the shore and historical sites of Oak Bluffs, get some delicious food at the Barn Bowl and Bistro! 


The lighhouse in Edgartown, Massachusetts.
The lighhouse in Edgartown, Massachusetts.

Another small town on the island of Martha's Vinyard, Edgartown, is more rural than its northern neighbor, Oak Bluffs. Wealthy whaling captains established this gorgeous town in the seventeen and eighteen hundreds. The rich past is still evident in the local architecture, with many original structures lining the streets. 

Many describe Edgartown as looking like a picture book. The beautiful homes, like the Doctor Daniel Fisher House and Old Whaling Church, still stand and grace the majestic scenery of this old-style town. If you want to experience some of the rural beauty of this village, visit Morning Glory Farm! This gorgeous picturesque farm has some photogenic sites and vibrant produce. That's not all, though. They also serve fantastic baked goods that are a must-try. 


Devereux Beach aerial view at Marblehead Harbor in town of Marblehead, Massachusetts
Aerial view of Devereux Beach at Marblehead Harbor in Marblehead, Massachusetts.

Marblehead might be a mainland Massachusets town, but it's best known for its scenic beaches and Children's Island. If you feel adventurous, you can take a short boat ride to the small yet lovely island and see its rugged beauty. But spend only some time on Children's Island because the downtown area provides so much to do and see! 

Many residents boast that Marblehead is the birthplace of the U.S. Navy. While this claim is sometimes contested, the truth is the first the town's modified vessel, the Hannah, served as the nation's first naval vessel in the Revolutionary War. One thing's for sure, though, the town is a fishing and sailing town much like its ancestors. 

Riverhead Beach is a great place to see the lovely Massachusetts shoreline and play in the splendid waters. The Marblehead Neck Wildlife Sanctuary is the perfect spot for bird and nature lovers, which isn't far from Riverhead Beach. After a beautiful day trekking outside, stop at Java Sun for coffee and refreshments! 


Phillip's Beach in town of Swampscott, Massachusetts
Aerial view of Phillip's Beach in Swampscott, Massachusetts.

Just to the west of Marblehead is the lovely little town of Swampscott. Don't let the name fool you; this town isn't a marshy wilderness. Swampscott is one of the prettiest towns in Massachusetts, with sunny shores, forests, and charming downtown. Philip's Beach is a gorgeous site that offers some of the best views of the sunset in the area. It's a slightly rocky shore, ideal for beach combing and rock collecting. You can also swim in the clear waters, but remember that lifeguards are only on duty between June and August. Fisherman's and Eisman's Beaches are other excellent places to make a day trip if you enjoy outdoor activities. 

However, if you prefer more restful activities indoors, there's plenty to do downtown. The Cookie Monstah is a cute cookie shop with baked goods and treats. Check out Chef Gloria B's nutritionist center to learn about health and wellness. After a long day of exploration, get some delicious food at Cindy's Pizza and Subs! 


Stockbridge, Massachusetts.
A street lined with boutique eateries in Stockbridge, Massachusetts.

Located just a few miles northwest of Hartford and Springfield, Stockbridge is a welcoming historic village not far from the border of New York. Stockbridge is a fantastic spot to see natural beauty mingling with charming colonial architecture. Preachers like Jonathan Edwards and missionaries were instrumental in the town's founding during the early 1700s, creating an early missionary settlement. The Stockton Bowl, a large lake in the northern regions of town, is the perfect spot for outdoor exploration. Right alongside this beautiful spot is the Gould Meadows, a stunning site with some excellent views worth photographing and sharing. 

Take some time to enjoy the old architecture dotted across town as well! The Edith Wharton Home is the breathtaking house of the creator who gave us The Age of Innocence and House of Mirth. Tours take place every day from 10 A.M. to 5 P.M. Also, visit Naumkeag, built in the 1870s with over 40 Voctorian-style rooms, overlooking the Housatonic River Valley. 


Beautiful homes of Nantucket, Massachusetts.
Beautiful seaside homes in Nantucket, Massachusetts.

Just a few miles west of Martha's Vinyard is Nantucket's quiet, beautiful, and stunning town and county. The first European explorer to find this island was Bartholomew Gosnold in 1602; however, settlers arrived approximately 50 years later. Nantucket wasn't part of Massachusetts until after 1692, when New York transferred ownership to Massachusetts. 

Nantucket offers some of the most breathtaking scenes in Massachusetts, with beaches, wildlife, and gorgeous colonial-era designs. Dionis and 40th Pole Beach are some of the cutest shores that afford plenty of space for fun and games. Visit the Nantucket Conservation Foundation to fully appreciate the town's natural beauty and varied ecosystems. If you get hungry, stop by Bartlett's Farm! The farm is worth experiencing, and they offer delicious home-cooked meals and freshly brewed coffee. 


Aerial view of Salem historic city center including Salem Witch Museum in city of Salem, Massachusetts
Aerial view of the historical city of Salem, Massachusetts.

Just north of Marblehead's small town is Salem's slightly larger village. Salem is infamous as the home city of the Salem Witch Trials of the 1690s. You can still visit the Witch House, where Judge John Corwin presided over the trials. However, Salem is so much more than its complex and diverse history. The history of this town is one of the many aspects that add to its charm and ancient significance. There are also plenty of outdoor activities, including exploring Water Island Park and Salem Harbor. 

Check out Notch Brewing and Coffee Time Bake Shop for rustic and delicious refreshments! Ensure you make plenty of time to visit this village because there's so much to see and experience. 


The beach at Provincetown, Massachusetts.
The beach at Provincetown, Massachusetts.

Unlike Salem, Provincetown's history was far less Puritan. Provincetown began as a port town where seafarers would dock and indulge after a long journey. Owing to its reputation as a port city, many Puritans of the day called the village "Helltown." 

However, Provincetown is anything but a hellish town. Located at the tip of the unique fishhook-like peninsula of Massachusetts in Cape Cod, this small town is full of natural beauty. From Long Point Beach to Clapps Pond, there's lots to explore and experience in this gorgeous landscape. If you plan on staying a few days, check-in at the welcoming and luxurious Brass Key Guest House. Get a bite to eat at the Lobster Pot. This fabulous restaurant serves fresh seafood in a stunning environment. 


The adorable town of Sandwich, Massachusetts.
The adorable town of Sandwich, Massachusetts.

Another lovely town in Cape Cod, Sandwich, was this county's first permanent settlement. It got its name from a town in England by the same name the early settlers thought it resembled. Quakers and other religious peoples were the earliest settlers of the site and gave the town its unique history. 

The Friends Meeting House, one of the earliest Quaker meeting places, still stands in town! It's certainly worth visiting if you love learning about early colonial history. Drop by the Lamberts Farm Market for home-cooked goodies and fresh produce! It's also a gorgeous site, meaning it grants some of the pretties views in town. 


Old Sturbridge Village, Sturbridge, Massachusetts
Old Sturbridge Village, Sturbridge, Massachusetts.

Sturbridge is known as the Crossroads of New England, dating back hundreds of years. European settlers used the town to connect the southern portions of the east coast with the northern regions. Before the arrival of English colonists, native people called the area Tantiusques, which is a name still applied to parts of the town. 

The Breakneck Brook Wildlife Management Center in the southern parts of town is ideal for hiking and cycling. This forest houses many birds and other animals, adding to this town's local charm and appeal. East Brimfield Lake and Long Pond are also excellent wildlife sites. Go fishing and hiking to take in all this small village offers! Visit B.T.'s Smokehouse for top-notch steaks and other delights. 


Uncle Tim's Bridge, in Wellfleet, Cape Cod, Massachusetts.
Uncle Tim's Bridge in Wellfleet, Cape Cod, Massachusetts.

Like Sturbridge, Wellfleet is a community steeped in history and natural splendor. Located in Barnstable County, Wellfleet was originally part of Plymouth. Settlers came to the area in the 1650s and established Wellfleet as a fishing community. Later, the town became a prominent farming community, and you can still see remnants of its history throughout the city. 

Just south of Provincetown, it's another charming community in Cape Cod. Jeremey Point is a spectacular beach in the eastern portions of town which makes for the perfect picnic spot. If you love the great outdoors, consider camping at the Wellfleet Hollow State Campground for a few nights!  The Beachcomber Restaurant is the best spot to drop by for fantastic food and cocktails. Located along the shore, you'll get a front-row seat to the sea while enjoying the foods the chefs offer. 

Massachusetts is one of the prettiest states in New England. This gorgeous state has a little bit of everything, including historic buildings from the colonial era, breathtaking shorelines, and nature reserves. Remember, several of the most remarkable islands in the northeast are located in this lovely region. If you're a fan of fishing, boating, world-class seafood, and hiking, Massachusetts is the place for you. Or, if you enjoy exploring ancient sites from the nation's founding, you won't be disappointed. 

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