Famous for its rugged coastline, pristine beaches, and delicious seafood, Massachusetts provides plenty of options when it comes to New England summer destinations. However, the Bay State has so much more to offer than that! The state is full of lovely small towns where you can spend a few days strolling up and down the main street, visiting historic sites, and enjoying the beautiful scenery. From the fabled towns of Plymouth, Salem, and Concord to the laid-back beach towns of Cape Cod, there’s something for history lovers, outdoor junkies, culture vultures, and everyone in between.
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Small Towns You Don’t Want to Miss
Below you’ll find a list of our favorite small towns in Massachusetts. These have been handpicked by our team of in-house travel experts based on the overall charm of the town, the shops and restaurants they have to offer, and the great things to do nearby.
The historic city of Boston is one of the most visited cities on the East Coast. While the city itself boasts a disproportionate number of historic buildings, there are also plenty of great towns nearby where you can see the history of Massachusetts, and the United States, come to life in front of you!
Lying just 20 miles northwest of Boston, Concord is a must-see for history buffs. Here, you’ll find Minute Man National Historical Park where a key Revolutionary War battle occurred following the Battle of Lexington and Concord. The British Army marched into the town on April 19th, 1775 with the hopes of destroying any arms or ammunition stored there. Luckily, the American soldiers had been warned about the invasion by Paul Revere and were able to move their supplies to a safe place. Instead, the Minutemen met the British Army at the North Bridge.
A few decades later, Ralph Waldo Emerson, Henry David Thoreau, Louisa Alcott, and Nathaniel Hawthorne used the area as a muse for their renowned essays, poems, and stories that are now an integral part of every high school literary education.
Founded in 1635, the town of Concord is undeniably handsome with red brick residences, family-owned farms, and bustling commercial areas. However, if you want to see what all the fuss is about, the first place you should visit is Walden Pond. This tranquil kettle hole lake inspired Thoreau, and many others, to put their deepest thoughts into words (maybe it was something in the water?). Their work eventually led to the birth of the conservation movement. Today, Walden Pond is a designated National Historic Landmark and visitors can explore the area much like Thoreau and Emerson did.
Located just one hour north of Boston, Rockport is one of Massachusett’s most popular beach towns and an ideal year-round spot for a day trip. This quaint coastal village offers historic buildings, interesting local businesses, and a sea of outdoor activities. During your visit, you can go kayaking, scuba diving, or whale watching. Or if you prefer to keep your feet dry, biking around Cape Ann or wandering around the waterfront is a great way to spend a few hours.
If you’re looking for some Instagrammable spots, head over to Motif #1 to snap a photo of the red shack. Built in the 1800s, this shack has served as a backdrop for many paintings and photos. When you get there, it’s very easy to see why! The scene couldn’t be more “New England” if it tried!
Halibut Point State Park is another great place to go if you want to get some great photos. The park offers hiking trails and tide pools surrounded by 400 million-year-old Cape Ann granite. If the weather is clear, you can see Mount Agamenticus in Maine as well as the Isles of Shoals which lies just off the coast of New Hampshire.
Best known for its horrific witch trials that are now one of its biggest tourist draws, Salem is a historic town located just north of Boston. The narrow streets boast well-preserved Colonial and Federalist architecture with many of the historic buildings dating back to the 18th and 19th centuries.
The 1692 Salem Witch History Museum is one of the best places to start learning about this infamous period of Salem’s history. Rather than simply focusing on the macabre, the museum looks at how witchcraft has been viewed by society throughout history, the human rights violations that occurred during the era, and, of course, how the witchcraft trials even happened in the first place. After increasing your understanding of the trials, you can then visit the Salem Witch Trials Memorial and the Proctor’s Ledge which was the site of the executions.
Once you’ve had enough witchy business, you can check out some of Salem’s other sites. Some of the highlights of the town include the McIntire Historic District which is home to most of the town’s most well-preserved historic homes, the Hammond Castle Museum, and the Salem Common which is the heart and soul of Salem.
Situated just 35 miles northeast of Boston, Newburyport is another great day trip destination. Settled in 1635, this historic seaport has exchanged whaling for tourism and it is now a very popular spot for boating and yachting. It is well-known for its picture-perfect Old World charm and its sprawling beaches.
Although just 11 miles long, Plum Island is the main attraction here. The island is only a 20-minute drive from the center of Newburyport. This barrier beach island is located on the migratory route for a large array of birds, making it perfect for bird-watching. It also offers one of the most family-friendly beaches close to Boston. While you’re there, make sure to visit the Plum Island Lighthouse, a cute little lighthouse that offers some great Instagram photo ops.
Cape Cod and the Surrounding Islands
Cape Cod and the surrounding islands are famous for their windswept beaches and stunning landscapes. However, the area is also dotted with a number of adorable small towns that are home to artists’ colonies, gingerbread houses, and more.
Situated at the northern tip of Cape Cod, Provincetown is home to one of the largest LGBTQ communities in the entire United States. Provincetown got its start as a Portuguese whaling and fishing port in the mid-18th century before slowly transforming into the vibrant town we know and love today. It’s even claimed to be one of the oldest art colonies in the country.
This eclectic colony of artists, writers, and creative minds has created a colorful beach community filled with culture. The town stretches three miles with streets lined with grand mansions, art galleries, boutiques, and eateries. If you want to let your hair down a bit while you’re there, make sure to visit The Atlantic House (also known as the A-House). Opened in 1798, this historic bar and dance club may be the country’s oldest gay nightclub.
More than 30 miles of beaches surround the town including the breathtaking Race Point Beach. Part of the Cape Cod National Seashore, these beaches provide the perfect place for some fun in the sun. From April until October, it’s a great place for spotting humpback whales. If you want to increase your chances of spotting Moby Dick, join one of the early-morning sightseeing cruises. While you are at the beach, don’t forget to stop by the early 19th-century Race Point Lighthouse. Listed on the U.S. National Register of Historic Places, this was one of the first lighthouses on Cape Cod to use a rotating beacon and has been guiding sailors to safety for over 200 years.
6. Oak Bluffs
With its lively downtown and adorable gingerbread summer houses, Oak Bluffs is one of the most visited towns on Martha’s Vineyard. It is located on the northeastern side of the island and has Martha’s Vineyard’s largest marina, making this a popular spot for yachting. The town is surrounded by sandy beaches where you go for a swim while the historic downtown offers an array of seafood restaurants and eclectic shops where you can browse around for hours.
If you’re traveling with kids, make sure not to miss the Flying Horses Carousel. Constructed in 1876 complete with real horsehair manes and tails and beady glass eyes, the carousel was originally located on Coney Island. It was then relocated to Oak Bluffs in 1884 and it has been taking very happy kids for a joy ride ever since!
7. Vineyard Haven / Tisbury
Vineyard Haven, also known as Tisbury, is home to Martha’s Vineyard’s largest port and the only operational port during the winter which means that this is the first stopping point for many tourists traveling to the Vineyard.
The town was chartered in 1671 during the reign of King James and became a prominent whaling station in the 1800s. Unfortunately, many of the town’s oldest buildings were destroyed in an 1833 fire but you can still find a handful of historic homes overlooking the harbor on William Street. The Martha’s Vineyard Seafaring Center is a great place to learn more about the history of the town and the impact that the maritime industry had on it.
However, if you’re itching to get out into the Great Outdoors, we highly recommend visiting the Manuel F. Correllus State Forest which features an extensive trail system that is perfect for hiking and cross-country skiing. The West Chop Lighthouse should also be at the top of your itinerary. Built in 1891, this historic lighthouse still has the original keeper’s house, oil house, and a garage which gives you a little more insight into the lighthouse’s early days than you normally get at other New England lighthouses.
Located just 30 miles off the coast of Cape Cod, Nantucket Island is fringed with pristine beaches, dotted with historic lighthouses and homes, and the adorable little town of Nantucket. It’s an ideal spot for everything from shopping, dining, swimming, and surfing. With its history dating back more than 400 years, it’s also a great place for history lovers!
Nantucket’s Main Street is lined with stately mansions and gray shingle-style New England cottages. The buildings once provided a refuge to whales and traders but today, they offer a place for weary travelers to lay their heads or to refuel on lobster rolls, sandwiches, ice cream, and coffee. Some of the homes also double as museums that you can take a tour of to learn a bit more about the history of the island.
One of the don’t-miss spots in town is the Nantucket Hotel. This late 19th-century building has long been a symbol of sophistication and class in Nantucket. There is a popular restaurant where you can grab breakfast, lunch, dinner, and Sunday brunch. If you have some spare time, you can also visit the Nantucket Whaling Museum to discover more about the role that whaling played in the development of Nantucket.
Once you have finished exploring the town, head over to the Coskata-Coatue Wildlife Refuge for a chance to see Nantucket’s wild side. With 16 miles of sandy roadways, rugged coastal trails, and family-friendly adventure trails, this is a great way to get up close and personal with some of Nantucket’s flora and fauna.
Lying between the western edge of Cape Cod Bay and farmland brimming with cranberry fields, Plymouth is less than an hour’s drive from Boston, but it may as well be in a different world. Home to the famous Plymouth Rock, Plymouth is often associated with being the first landing spot of the Pilgrims when the Mayflower finally reached the shores of North America.
As you can imagine, many of the must-see sights in Plymouth revolve around the Mayflower and its occupancy. There is a replica of the original ship docked in the harbor while the Plimoth Plantation offers recreations of the original 17th-century villages where the Pilgrims lived.
When it’s time to wet your whistle, you can visit one of the many microbreweries in town or go to the Plymouth Bay Winery and raise a glass in honor of these adventurous souls who risked their lives to start a new life in North America.
Lying on the tip of Cape Cod, Chatham is an idyllic seaside town boasting a gorgeous 19th-century lighthouse and a string of windswept beaches. It’s a popular destination for anyone wanting to get a taste of Cape Cod. Besides the picture-perfect Main Street, one of the biggest attractions in Chatham is the Chatham Fish Pier where you can watch playful seals beg the local fisherman for a bite to eat.
Nature lovers will also enjoy the Shark Center Chatham where you can learn more about Great Whites and the Monomoy Wildlife Refuge. Spreading more than 7,600 acres, the refuge features salt and freshwater marshes, tidal flats, and sand dunes. It’s a great place for bird watchers. You can even watch migratory species glide through the sky from the refuge’s observation tower.
Western Massachusetts is often passed over for the more exciting coastal cities and towns. However, this is a bit of a shame as this side of the state offers beautiful scenery, historic sites, and charming small towns.
Nestled in the Berkshires just a few hours’ drive north of Connecticut and New York’s Hudson Valley, Stockbridge feels just like a Norman Rockwell town – because it is one. Stockbridge boasts a main street with a handful of shops, cafes, and restaurants that look like they have barely changed in 70 years.
During your visit, don’t miss The Red Lion Inn. Built in 1773, this historic inn is the heart of Stockbridge. Although the original structure was destroyed at the end of the 19th century, it was rebuilt and reopened in 1968. Today, it’s home to 82 guest rooms, two bars, and a dining room. Stepping inside of the inn is almost like going back in time.
The Berkshire Botanical Garden is one of the highlights of Stockbridge for many visitors. Founded in 1934, this 24-acre botanical garden is one of the oldest botanical gardens in the northeastern United States. It has more than 3,000 species and varieties of herbaceous and woody plants spread across a dozen different gardens.
If you are a fan of Norman Rockwell’s idyllic paintings of everyday life in 20th-century America, you should visit The Norman Rockwell Museum. Rockwell spent the last 25 years of his life living in Stockbridge and this museum is dedicated to Rockwell’s life and work and exploring the impact that it had on American culture. The museum has a collection of more than 100,000 items including original art materials, personal belongings, furnishings, and Rockwell’s library.
The final place that you should be sure not to miss is Naumkeag. This public garden and 44-room historic home is located on 48 acres of manicured land. It was built in the mid-1880s by Joseph Choate, the U.S. Ambassador to Great Britain as a summer retreat. It was designed by the architecture firm of McKim, Mead & White (who also designed Central Park) and many generations of the family lived on the property until the late 1950s. Today, it’s open during the summer months, and it’s a lovely place to experience Gilded Age style and splendor.
Home to the Shakespeare & Company and Tanglewood, the summer home of the Boston Symphony Orchestra, Lenox is a wonderful place to go for anyone who loves the performing arts. Opened in the 1930s, Tanglewood has hosted performances by some of the world’s most renowned musicians including James Taylor, Earth, Wind & Fire, the Goo Goo Dolls, and Josh Groban. It’s a beautiful outdoor venue and the perfect place to catch a summer show.
Lenox is also an awesome destination for history lovers thanks to the town’s Ventfort Hall Mansion and The Mount. Built in 1893 by Sarah Morgan, J.P. Morgan’s sister, Ventfort Hall is a Jacobean Revival-style mansion that offers an in-depth look at Lenox’s Gilded Age history. It is now listed on the National Register of Historic Places and is an iconic destination in town. Meanwhile, The Mount is the former estate of beloved writer Edith Wharton who was the first woman awarded the Pulitzer Prize for fiction.
Ready to roam?
We hope this list of the best small towns in Massachusetts has inspired you to plan your next getaway to The Bay State. If you would like to read more about all of the amazing things on offer in New England, make sure to head over to the Let’s Roam Explorer blog. Here, you’ll find hundreds of travel articles, destination guides, and must-visit lists for destinations around the country. You can also download the Let’s Roam app which gives you access to all of our great app-based scavenger hunts as well as user-generated travel tips and tricks.
Frequently Asked Questions
Massachusetts is full of small towns that are perfect for history and nature lovers. Some of the best ones to check out include Concord, Salem, Stockbridge, Nantucket, Oak Bluffs, and Lenox.
If you’re planning a road trip to Western Massachusetts, make sure not to miss the amazing small towns of Stockbridge and Lenox. They’re full of historic sites, mom-and-pop shops, and restaurants.
Salem, Concord, Rockport, and Newburyport are some of the most beautiful small towns near Boston. All are located within a few hours’ drive and most wonderful scenery, eateries, and historic buildings.
If you’re visiting the Cape Cod area, don’t miss the idyllic small towns of Provincetown, Oak Bluffs, Vineyard Haven, and Chatham. Surrounded by beautiful beaches, these are great for a summer getaway!
If you’re on a New England road trip but a bit short on time, you can easily visit many of the best small towns in Massachusetts within a few days. Many towns are located close together and easy to reach.