Traditional American Whithe Church with high Steeple under an Autumnal Blue Sk. Williamstown, MA.

Top 20 Things To Do In Massachusetts For Your New England Bucket List

Do you have a New England bucket list? Here are our top 20 things to do in Massachusetts. Although Boston is simply a must-see destination in New England, there are so many reasons to visit Massachusetts from exploring small towns in Massachusetts to outdoor activities in Massachusetts for the whole family to enjoy. Your Massachusetts bucket list should include the many things to do in the Berkshires, museums in Massachusetts, the Black Heritage Trail and colonial architecture in Massachusetts. Discover why Massachusetts is quintessentially New England.

Things To Do in Massachusetts

You probably think you know Boston even before you visited because you have seen Boston often in the movies.  Boston and Massachusetts are famous for its connections to American history as well as its many institutions of higher learning. With over 100 colleges in Massachusetts (with lots congregated in/near Boston itself), lots of Americans have spent time in the state themselves.

green postcard with the words: "Greetings from Massachusetts U.S.A.'
Top 20 Things To Do In Massachusetts For Your New England Bucket List

There are plenty of things to do in Massachusetts throughout the year in all seasons and whether you are visiting for a day trip, a weekend or longer. Cape Cod and the islands are often considered the quintessential New England summer holiday. The Berkshires is famous for summer getaways, fall foliage and winter skiing.

Visit Boston

You’ll need at least two days to tour Boston, the oldest city in the USA and the biggest city in New England. There’s so much to see and do in Boston for a relatively small city. Even though the population is only approximately 700,000, it’s the biggest city in New England AND home to most of the population in Massachusetts.

Old State House and the skyscrapers of the Financial District at night in Boston, Massachusetts, USA
Old State House in Boston, a bucket list Massachusetts item and a stop on the Freedom Trail

For example, Boston Common is the oldest public park in the United States and the Boston Museum of Fine Arts is one of the best in the world. Take the 3 mile trail known as the Freedom Trail which contains 16 places essential to the birth of the nation. Join the debate on who has the best cannoli in Boston’s North End and have a Boston creme cake in the restaurant where it was invented.

For History Buffs

Established in 1620, Boston has a lot of history packed into its cobblestone streets including some notable firsts like the first public school in the country (Boston Latin), the first university (Harvard), and the first newspaper printed in the colonies. The rest of Massachusetts is also chock full of history including its own firsts such as the first landing of the Pilgrim fathers and the first battle of the American Revolution.

Learn About American History

Thanks to the Pilgrims establishing Plimoth Colony and as the home to many founding fathers, Massachusetts has got a big role in American history. For example,

  • Visit Plymoth Rock and the Mayflower II at Plymouth. Ever November, Plymouth pus on the America’s Hometown Thanksgiving celebration.
  • Everyone  has heard of Salem thanks to the famous witch trials. The house of the judge of the Salem Witch Trials is open to visitors.
  • The 970 acre Minute Man National Historic Park in Lexington commemorates the opening salvos of the American Revolution.
  • The Susan B. Anthony Birthplace Museum in Adams, the famous women’s suffragette and Chesterwood, home of the man who created the famous Lincoln statue at the Lincoln Memorial in Washington, D.C..
  • The American Heritage Museum in Hudson Massachusetts is a commemoration of World War II.
Plymouth Rock in Plymouth MA
Visiting Plymouth Rock is a New England bucket list item for many people.

Take in A Living History Museum

Maybe it’s all the university students who need summer jobs but Massachusetts has a handful of living history museums.

Plimoth Plantation is a living museum that recreates what life was like for the early settlers who arrived in 1620 as well as a Native American settlement nearby.

Storrowtown in West Springfield is a reconstructed village of 18th and 19th century buildings from Massachusetts and New Hampshire.

Old Sturbridge Village is another living museum that shows what New England life was like during the 19th century.

houses and carriage at Old Sturbridge Village in Massachusetts
Living history museum, Old Sturbridge Village, is a Massachusetts bucket list item.

With about 20 buildings, Hancock Shaker Village shows how this religious sects lived. The Shakers founded the village in 1783 and believed in communal ownership, beautiful craftsmanship and celibacy. With no new little Shakers born the Shakers had gone extinct by 1960.

Black Heritage Trail

One of the victims of the Boston Massacre was a runaway slave, Crispus Attucks. Beacon Hill’s north slop was the home to a community of free African Americans in the 19th century. The African Meeting House built in 1805 was their place of worship and in 1832 saw the establishment of the New England Anti-Slavery Society. Boston was the home of the first African American regiment in the US Civil War.

In Boston, National Park members lead tours of the Black Heritage Trail. Thanks to the presence of large numbers of Quakers, Nantucket was fervently anti-slavery and also has an African Meeting House. The Minute Man National Park has a building which was part of the Underground Railroad.

In Martha’s Vineyard, the Black Heritage trail is a self-guided tour. Abolitionist, Frederick Douglass spoke at the Federated Church in Edgartown in 1857 – an event commemorated every Fourth of July in Martha’s Vineyard with the reading of the speech in Edgartown and at the Inkwell Beach in Oak Bluffs, a traditional gathering spot of African American visitors to the island.

A bench in front of Inkwell Beach
Benches face onto the famous Inkwell Beach and Nantucket sound.

Maritime Heritage

The Massachusetts coastline has shaped how the state developed. Marblehead and Salem both have a long and rich maritime heritage. Gloucester Massachusetts is still a working fishing town. The dangers of fishing were thrust onto the national spotlight with the 2000 film set in Gloucester, The Perfect Storm.

Fisherman statue at the harbor of Gloucester in Massachusetts
Gloucester’s Fisherman’s Memorial in the harbor pays tribute to the maritime heritage of the town.

The Whaling Museum in New Bedford captures what it was to be the worlds’ most important whaling port in the 19th century. The Nantucket Whaling Museum traces how important whaling was to the island’s fortunes.

The Maritime Museum at Battleship Cove is renowned for its Titanic Exhibit. Moreover, ships like the USS Massachusetts at Battleship Cove commemorate the maritime heritage and the naval military history of New England.

Outdoor Activities in Massachusetts

Outdoor activities in Massachusetts are a plenty – from the beautiful countryside in the Berkshires to an extensive coast line of stunning beaches.

Take a Scenic Drive

Take a scenic drive through Massachusetts to explore its small towns, natural habitats and varied geography. The Mohawk Trail is a 63 mile drive through beautiful countryside in the Berkshires. MA 127 is a 27 mile route through salt marshes, beaches  and charming towns like Rockport on Cape Ann. Route 6A on Cape Cod weaves its way through cute little villages and sand dunes.

Autumn view from Golden Eagle Restaurant hairpin overlook on the Mohawk Trail - Berkshire Massachusetts
Autumn on the Mohawk Trail is perfect for a scenic drive.

Fall foliage hits peak splendour in the Berkshires in the middle of October generally. Make sure to visit Mt Greylock for views that can stretch up to 100 miles over the colourful trees below. Time your leaf peeping right and you can even make the Fall Foliage Parade held annually in North Adams to lure in that sweet tourist money.

Go To The Beach

On the North shore, Manchester by the Sea has a beach which sounds like its singing (under certain conditions the sand grains squeak). Also north of Boston, Wingaersheek Beach in Gloucester is popular with families. Plum Island has miles of beach on a barrier island.

sunset on Moshup Beach in Aquinnah Martha's Vineyard
Visiting the beaches are a great thing to do in Massachusetts.

Most of the beach action in Massachusetts happens south of Boston heading for Cape Cod and the islands. Cape Cod has miles of protected beach at the Cape Cod National Seashore. Our favourite public beaches in Martha’s Vineyard are dotted throughout the island. Unlike Martha’s Vineyard, all of Nantucket’s beaches are public.

Further south heading for Rhode Island, Horseneck Beach State Reservation has both marshland and a pretty beach.

Animal Encounters Massachusetts

There are whale spotting tours that run regularly from various places such as Boston, Gloucester and Provincetown to Stellwagen Bank which is a National Marine Sanctuary of 842 square miles located between Cape Cod and Cape Ann. In addition to whales, you can also spot dolphins and seals.

There are thousands of seals, mostly harbor seals and grey seals, on Cape Cod waters as well. The thriving seal population has attracted sharks (and made the area famous with the blockbuster movie, Jaws).

welcome to Chatham sign in Cape Cod
Chatham in Cape Cod is a charming seaside town and close to where seals (and sharks) hang out.

If you would like to see your marine life in an indoor setting, check out the New England Aquarium in Boston or the Woods Hole Science Aquarium in Cape Cod.

Go For Hikes in Massachusetts

Hikes in Massachusetts are a joy. You can hike on the rail trails that the bikes use so they are mostly flat and easy to walk.  In Boston, the Emerald Necklace runs for about 32 miles. For great views of the Boston skyline, check out the World’s End coastal park in Hingham. Outside of Boston, the Housatonic Riverwalk in Great Barrington is a recreational trail which runs about 5 miles.

Directional and Information Signas at the Beginning of a Mountain Trail
The Berkshires have a part of the Appalachian Trail cutting through it.

There are miles of hiking trails in the Berkshires including the 9 miles of the Appalachian trail pass through Massachusetts. Check out the trails at Natural Bridge State Park and Mount Greylock State Reservation.

Cape Cod and and the islands also provide great hiking paths, such as the Great Island Hiking Trail on the Cape Cod National Seashore.  Menemsha Hills is a lovely cliffside walk on Martha’s Vineyard. None of the walks on Martha’s Vineyard are too difficult and are great for walkers of all abilities to enjoy together.

Massachusetts Sports

Boston is nuts about sports and home to the region’s national teams – the Boston Red Sox (baseball), Boston Bruins (hockey), Boston Celtics (basketball). New England’s football team, the New England Patriots, is in a suburb of Boston at Foxboro. Held every spring, the Boston Marathon is the world’s oldest annual marathon.

Boston Strong ribbon commemorating the Boston Marathon bombing in 2013
A premier Massachusetts sports event, the Boston Marathon, was rocked by two bombs in 2013.

Fenway Park, built in 1912m is a must visit whether or not you are a baseball fan. The Hall at Patriot Place is a museum for the New England Patriots. Home to both the basketball and hockey teams, two floors of the TD Garden also hold the Sports Museum of New England. Naismith Memorial Basketball Hall of Fame in Springfield pays homage to the sport’s history and greats in the USA.

Want to join in the sporting fun as well as watch it? Massachusetts has so many options on land and sea – cycling, kayaking and skiing to name a few. If you consider bowling a sport, the little known variant candlepin bowling was invented in Massachusetts.

Bike the Cape Cod Rail Trail which has 22 miles of paved trails. In the winter, the same paved trail is great for cross country skiing. There are other rail trails too – in Cape Cod there is also the Shining Sea Bikeway, the Norwottuck Rail Trail between Amherst and Northampton and the Ashuwillticook Rail Trail from Pittsfield to Adams in the Berkshires.

Shining Sea Bikeway in Cape Cod
Outdoor activities in Massachusetts include cycling along the many bike trails.

Cycling is also a popular way to get around Martha’s Vineyard and Nantucket. Smaller and flatter, Nantucket has easier cycle paths than Martha’s Vineyard. For a challenge, cycle the entire island of Martha’s Vineyard which will take a few hours.

Get Cultured

No doubt considered the spiritual home of the intellectual elites (or at least Harvard). you will have your choice of arts events to appreciate in Massachusetts.

Enjoy the Arts

As befitting a major city, Boston is well know for the arts but that’s the only place in Massachusetts for cultural events. Yet, the Berkshires in the summer has a huge arts scene to rival any place in the world.

The open-air Tanglewood Festival in Lenox is for music lovers – 350,000 music lovers annually to be precise. The Boston Symphony Orchestra decamps to Lenox during the summers and occasionally plays with the Tanglewood Festival Chorus. Williamstown Theater Festival is an annual drama event when Williams College breaks up for the summer.

audience watching play at the theater
Summer in the Berkshires is a Massachusetts bucket list item

Taking place in Becket in the Berkshires, the Jacob’s Pillow Dance Festival is the oldest summer dance festival in the country. Mass MoCA in North Adams sprawls over 25 buildings with includes galleries and performance centres.

Cape Cod and the Islands have many arts events happening for the summer as well. For something completely different from the usual Western culture oriented arts scene, check out the Mashpee Wampanoag Powwow for dancing, drumming and other aspects of Native American culture.

Quirky Museums Massachusetts

Boston has major museums of which our favourite is the Isabella Gardner Museum with its art collection located in a faux 15th century Venetian Palace. My other personal favourite is the Museum of Bad Art which has several branches in the suburbs of Boston.

Some of the more interesting quirky museums in Massachusetts are outside of the Boston area. For example, Lowell Massachusetts was famous for its textile mills and factories during the Industrial Revolution. Now, the American Textile History Museum tells the story of New England’s famed textile industry and the New England Quilt Museum is devoted to this textile craft.

ign outside of the Salem Witch Museum which tells the story of the 1692 witch trails in Salem, Massachusetts
The Salem Witch Museum tells the story of the Salem Witch Trials of 1he 17th century which have continued to fascinate generations later.

The reputedly haunted Lizzie Borden House in Fall River is both a bed and breakfast and a museum to the infamous double murder of the Bordens  in the 19th century. In the Berkshire, Animagic – Museum of Special Effects and Animation will be of interest for the whole family.

And, then you hit random things like the The Museum of Russian Icons in Clinton which has one of the world’s largest collections of Russian icons. Why? It’s from a private collection of a icon enthusiast with money to indulge in his passion.

Art Museums Massachusetts

Venture outside of Boston to Cambridge and you’ll find the Harvard Art Museums have an extensive collection. Further afield, the Norman Rockwell Museum in Stockbridge pays tribute to an artist who has become synonymous with the Americana that he painted from his home in Stockbridge. Established in 1896, the Worcester Art Museum has a well-regarded collection of American, European and Asian art.

The Clark Art museum building view from the park
The Clark Art Institute in Williamstown Massachusetts

Other colleges also have incredible art museums. For example, the Clark Art Institute, and its relation, the Williams College Museum of Art, have a large collection of Impressionist and American art. The Smith College Museum of Art in Springfield has a massive collection of European and North American art, especially Edgar Degas and Winslow Homer.

Explore Colonial Architecture in Massachusetts

Historic Deerfield Village shows off federal and colonial architecture in a charming village setting. Salem has a wide range of buildings as part of the Peabody Essex museum including the John Ward House from 1684, the 1727 Crowninshield-Bentley House and a 18th century Chinese building from Huizhou.

he 1727 Crowninshield-Bentley House at the Peabody Essex Museum
The 1727 Crowninshield-Bentley House at the Peabody Essex Museum

Famous Writers in Massachusetts

Massachusetts has a long history with authorship beginning with Anne Bradstreet from Boston becomes the first published writer from the American colonies in 1650. Examples of other places you can visit include:

  • Nathaniel Hawthorne’s birthplace and the House of the Seven Gables in Salem, immortalised by his book of the same name.
  • Dr Seuss National Memorial Sculpture Garden in Springfield which has a life size bronze statues of the famous characters from Dr Seuss’ books
  • the home town of Beatnik author Jack Kerouac in Lowell with celebrates with an annual festival
  • Arrowhead which is the home of author, Herman Melville, famous for his work, Moby Dick
  • Edith Wharton’s estate, The Mount, in the Berkshires

Lots of early American writers settled in Concord, such as Ralph Waldo Emerson, Henry David Thoreau and Louisa May Alcott. You can visit Alcott’s home, Orchard House, where she wrote her famous work, Little Women. There is a replica of Thoreau’s cabin on Walden Pond, located within a state nature reserve.

replica of Thoreau's cabin on Walden Pond
Replica of Thoreau’s cabin on Walden Pond

Amherst is home to two very different authors. Located in her birthplace and home, the Emily Dickinson Museum is dedicated to the 19th century poet.The Eric Carle Museum of Picture Book Art celebrates the author of the children’s classic, The Very Hungry Caterpillar.

Quintessential New England

Quintessential New England is associated with beach holidays in the summer, fall foliage drives and charming little villages covered in snow. Massachusetts has all that and more which can go a long way towards filling up your New England bucket list.

Fun in the Berkshires

The Berkshires presents the New England that everyone pictures – little towns with white spired churches and rolling green hills. The Berkshires in Massachusetts have long been where wealthy people from Boston and New York City fled their cities for a rural idyll. Part of that self care is that now the Berkshires are home to well known spa resorts such as Miraval Berkshires Resort and Spa and Canyon Ranch Lenox.

Traditional American Whithe Church with high Steeple under an Autumnal Blue Sk. Williamstown, MA.
For quintessential New England meet Williamstown

Small Towns in Massachusetts

Small town in Massachusetts really does mean small. After Boston, Worcester (population 170,000) is the second largest city in Massachusetts.

North of Boston, Rockport and Newburyport are a charming fishing villages that are picture perfect. Cape Cod and the islands have their small town charmers too. On Cape Cod, Chatham and Harwich are genteel while Provincetown is more colorful. In Martha’s Vineyard, you have the beach town atmosphere of Oak Bluffs, the genteel captain’s houses of Edgartown and the bucolic charm of West Tisbury.

Menemsha village shrouded in mist
The fishing village of Menemsha, made famous in the 1995 remake of Sabrina

When visiting small towns in Massachusetts, remember the college towns that bring youth and trendiness to what would be an otherwise small town in New Englan. For example, Williamstown centres itself on prestigious Williams College. the college town of Amherst is the home to three institutions of higher learning, UMass Amherst, Amherst College and Hampshire College. Thanks to the influence of Smith College, Northampton has charming cafes, trendy boutiques and art galleries.

Visit Cape Cod and the Islands

Cape Cod itself has hundreds of miles of shoreline. Split into 4 regions depending on where it is located on the peninsula, each section of Cape Cod has its own identity. Provincetown on the Outer Cape is the undisputed party town with its inns, shops and restaurants.

The protected status of the Cape Cod National Seashore means it has remained largely unchanged as the rest of the area has grown with modern times. Cape Cod and the islands are a perfect place for a multi-generational family holiday which is why people return year after year with their families.

Vineyard Haven harbor on Martha's Vineyard at sunrise
Vineyard Haven harbor on Martha’s Vineyard at sunrise

The six towns of Martha’s Vineyard are spread amongst the miles of beaches and countryside. Even smaller and completely flat,  Nantucket is known for its grey shingled houses. The Martha’s Vineyard lighthouses and Nantucket lighthouses recall a time when these islands were important ports of call for the whaling industry.

Eat, Drink and Be Merry

You can eat your fill of quintessential New England food like clam chowder, fried clams and lobster.  Seafood is plentiful, often fried and fairly cheap. Look out for festivals like the annual Chowderfest in Boston in July and the Wellfleet Oysterfest in October.

There’s plenty of great food also if you venture beyond seafood. Boston is traditionally known for its baked beans, cream pies and Parker rolls as well as great Italian food. There’s also the famous Cape Cod Potato Chips as well as the millions of gallons of Ocean Spray Cranberry Sauce consumed every year at Thanksgiving.  Foliage viewing wouldn’t be complete without cider apple donuts.

tray of Boston cream cupcakes
The Omni Parker House is a legendary hotel credited with many stories, including the creation of the Boston Cream Cake.

Craft beer is huge in Massachusetts. In Boston take a Sam Adams Brewery tour, a microbrewery founded in Cambridge. Northampton Brewery is the oldest brewpub in New England. Although Tree House Brewing Company in Charlton is not sold in stores, people come from wide and far to wait in line for their beer.

Massachusetts does have its vineyards especially in the southern part of the state. Judging by the crowds, Truro Vineyards on the Cape is an extremely popular place to hang out. Personally, we have been spoiled by French wine and will reserve our praise.

Check out the Antiques in Massachusetts

It stands to reason that one of the oldest states in the Union would have a treasure trove of antiques and vintage goods.   River Street and Charles Street in Boston have excellent antique shops. The town of Essex also has a large selection of antique stores to browse.

an antiques fair with passerby in the background
The search is half the fun when you shop fairs.

Thousands of people descend on little Brimfield Massachusetts every May, July and September for the weeklong extravaganza that is the Brimfield Antique Show and Flea Market. Bring your walking shoes to Brimfield which is quite the experience and simply ginormous.

Map of 20 Things To Do in Massachusetts


Pinterest image of a New England style White House with black shutters and the text: " 20 Bucket List Things To Do in Massachusetts"
Our pick of things to do in Massachusetts for a New England trip includes a variet of Massachusetts travel things to do. For example, bucket lists usually include Boston travel, whale watching, road trips, cape cod vacations, fall foliage tours, and things to do in the Berkshires. The best places to visit in Massachusetts include Gloucester, Salem, the Berkshires, Cape Cod, Martha’s Vineyard and Nantucket – many of which are must see places in the US. Discover what makes Massachusetts special!

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