Massachusetts Bucketlist: The 24 Best Places to Visit

Most visitors think of Boston, Salem, or Cape Cod as the most popular places to visit in Massachusetts. But there’s so much more to the Bay State than meets the eye. As a local, I can attest to Massachusetts’ interesting and unique destinations.  

Massachusetts is a place where history and culture meet. From major cities to seashore towns, and everywhere in between, there is something for everyone. I’ve created this list to help you explore the best of Massachusetts while enjoying all the top attractions.

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Best Places to Visit in Massachusetts

Salem

One of the oldest towns in North America, full of history and mystery. 

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Salem, Massachusetts, draws visitors from around the world for its historic Witch Trials and spooky celebrations. Today, Salem preserves its history and artifacts through local museums and guided tours.

The Salem Witch Museum explores the 1692 Salem Witch Trials that put Salem on the map. The House of the Seven Gables is another one of Salem’s essential stops. It is a historic home, museum, and a designated National Historic Landmark. 

The Peabody Essex Museum (PEM) is another Salem museum and one of the fastest-growing art museums in North America. Salem is most popular in the fall, as this is the best time to visit for the full Salem experience. 

The Berkshires

A one-of-a-kind highland region in Western Massachusetts full of green hills and stunning foliage.  

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The Berkshires are a highland region in Western Massachusetts that offers beautiful year-round scenery with the best in nature and recreation. You’ll find historic villages, a thriving art community, diverse terrain, and wonderful places to stay.

Enjoy outdoor adventures such as hiking trails and cross-country skiing. Or, take in the impressive collection of cultural and historic sites like Edith Wharton’s Home “The Mount” in Lenox, and the Norman Rockwell Museum in Stockbridge. The Berkshires are most popular in the fall.

Cambridge

This city sits across the Charles River from Boston and is home to the renowned Harvard University.

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The city of Cambridge has its own distinct charm and identity, despite being so close to Boston. The city is best known for being the home to the historic Ivy League university, Harvard University.

Take a tour of Harvard’s campus but feel free to explore other parts of Cambridge, too. From unique city squares to history, art, architecture, and restaurants, there’s plenty to do.

I love to stroll down Memorial Drive. This street runs along the Charles River. It offers outstanding views of the Boston skyline, especially at night. 

Be sure to check out the Head of the Charles regatta (boat race) if you visit in late October. This is the largest regatta in the world where athletes compete in rowing. The background of fall foliage makes it a unique event to experience.

Boston

Boston has something for everyone with its rich history and diverse neighborhoods. 

📍 Google Maps | Top Places to Stay in Boston

Boston is the largest city in Massachusetts and is best known for its storied history. It has a legacy of culture, arts, and education dating back to the 1600s. Today, Boston offers a blend of historical sites, modern attractions, and waterfront views. 

Visit the Boston Tea Party Ships & Museum to see the only surviving tea chest from the historic Boston Tea Party protest. Another popular historic attraction is the Public Garden, which dates back to the 1800s. Here, you can watch swan boats float along the lagoon.

There’s plenty to do for those visiting Boston with children. Places like the New England Aquarium and the Boston Children’s Museum will guarantee a great time. 

For culture enthusiasts, stop by the Isabella Stewart Gardner Museum to browse the fine art. Or, perhaps take in a show at the Boston Symphony Orchestra. 

For more, see my full list of stuff to do in Boston.

Harvard University

The oldest institution of higher learning in the United States, highly regarded for its influence and reputation.   

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Harvard University is located in Cambridge, Massachusetts. The Ivy League university dates back to 1636 and has been esteemed in higher education for 387 years. 

Anyone can visit the Harvard campus. Many student-led tours cover the University’s historic buildings, dorms, and more. After touring the campus, explore the historic neighborhood of Harvard Square. It is full of shops, restaurants, cafes, and laid-back bars. 

Buy a book at the Harvard Book Store. This independent bookshop has been a Cambridge landmark since 1932. Then grab a bagel at my favorite bagel spot at Black Sheep Bagel Cafe.

Old Sturbridge Village

The largest outdoor history museum in the Northeast with re-created settlements and period re-enactors.   

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Visiting Old Sturbridge Village is like taking a journey through time to the 1830s. This living museum invites visitors into its more than 40 historical buildings. These include homes, meetinghouses, shops, and more.

Historical re-enactors carry out the daily activities of this early 19th-century community. Wander through the different shops that make up this village. You can also visit with a farmer plowing the fields or a blacksmith hammering away. 

There are more than 200 acres to explore at Old Sturbridge Village, so there is always something new to experience. Overall, Old Sturbridge Village is a wonderful place to bring the whole family.

Freedom Trail

A 2.5-mile pathway through Boston’s most historic buildings and sites.  

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The Freedom Trail path runs 2.5 miles through several of Boston’s most historical sites and attractions. This is one of Boston’s top tourist attractions. Walking the Freedom Trail is a great way to get acquainted with American History. 

The Freedom Trail begins at Boston Common and ends at the Bunker Hill Monument. You will pass through 16 historical landmarks while learning about the American Revolution.

Beacon Hill

One of the most picturesque neighborhoods in all of Boston.  

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Beacon Hill is a historic neighborhood in Boston. With its charming brownstone-lined streets, it’s one of Massachusetts’ most famous areas as well as one of my favorite spots.

While walking through the streets of Beacon Hill, you may notice a building with a golden dome. That’s the Massachusetts State House. It has housed the state’s government since 1798. Learn all about Massachusetts History by taking a free tour.

Concord

Head 30 minutes outside of Boston to find history, culture, and nature in one city. 

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Concord is home to American Revolutionary War sites and is only a 30-minute drive from Boston. A key battle of the American Revolution took place at the Old North Bridge in Concord. 

Put the Minute Man National Historic Park at the top of your list when you visit. This piece of land is 970 acres of trails, exhibits, and monuments. The historic park is shared between Concord, Lexington, and Lincoln, Massachusetts.

There are plenty of things to do for the entire family in Concord. The city is home to theaters, museums, and is easily accessible to nature. The town offers beautiful views of the river.

Medford

This city has a thriving community and offers a unique blend of history. 

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Medford is a city that offers a blend of urban vibrancy and suburban tranquility. There is a unique history here, with peaceful town centers and quiet side streets.

Medford is perfect for those who enjoy outdoor recreation. There are plenty of green spaces, such as the Mystic River State Reservation. This area is popular for hiking, biking, and picnicking. 

Medford is a city that is deeply connected to American history, dating back to 1630. The legendary Paul Revere rode through Medford during his historic ride. Every year, Medford does a reenactment of this ride to honor his legacy. It is part of the Patriots Day celebration in April.

Boston Harbor Islands National & State Park

A unique collection of bays, harbors, and rivers off the coast of Boston.

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The Boston Harbor Islands National & State Park covers 34 islands and peninsulas. It’s filled with hiking trails, lighthouses, tidal pools, campgrounds, and much more.

You can go fishing, picnicking, swimming, and camping under the stars all within reach of downtown Boston. Deer Island offers amazing city views where you can watch the planes take off from Logan Airport.

Stockbridge

A charming town in Berkshire County in Western Massachusetts. 

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Stockbridge is a picturesque village in the Berkshires of Western Massachusetts. The small, lively town has many fun things to do.

Start at one of the most iconic places in town: The Red Lion Inn. This hotel first opened as a tavern back in 1773. It still retains its colonial features. Stop by, grab a drink, and sit on the porch to watch the day pass by. 

American painter Norman Rockwell spent his later years in Stockbridge. Now there is a beautiful museum dedicated to his work. The art museum has the world’s largest collection of his paintings.

New Bedford

A famous port city just outside of Boston, which was once the whaling capital of the world. 

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The city of New Bedford was once the whaling capital of the world during the 19th century. Today, New Bedford leans heavily into its history, but the city is growing with new restaurants, parks, and art galleries.  

I recommend visiting the New Bedford Whaling Museum. This museum details the city’s complicated whaling history. You’ll find a collection of whale skeletons, a whaling ship replica, and artwork. You’ll also learn about the biology of whales and current conservation efforts.

Plymouth

A waterfront town that’s home to some of America’s most iconic historical monuments.

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Plymouth is a picturesque waterfront town in Massachusetts. There’s plenty of local charm and historical monuments to discover. 

Head to Plymouth Rock in Pilgrim Memorial State Park. Plymouth Rock is an iconic American landmark and a symbol of the nation’s beginnings. The famed rock is known as the place where the first Pilgrim settlers set foot on land in Massachusetts. 

Experience where American history took place at the Plimoth Patuxet Museum. This outdoor history museum is a recreation of a pilgrim village and an immersive experience with historical activities to enjoy.

Adams National Historical Park

A historical park in Quincy that was the former home of two U.S. presidents and notable American figures.

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The Adams National Historic Park is a historical site and home of American presidents John Adams and John Quincy Adams, as well as their families and descendants. The historic park is located in the town of Quincy outside of Boston. 

Here, you can tour the historic family homes. These homes include John Adams and John Quincy Adams’ birthplace, The Old House at Peacefield. Be sure to reserve tickets for home tours ahead of time!

The second U.S. President, John Adams, lived a full life as a farmer and a world traveler, and helped author the Declaration of Independence. Take in the architecture, art, literature, history, and gardens at this historical attraction — it’s sure to make for a fascinating day.

Marblehead

This overlooked area is home to quaint harbor towns and well-preserved historic homes.

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Marblehead is a town that is often overlooked by its neighboring witch city, Salem. Just a 50-minute drive from Boston, you can take in a gorgeous harbor and dreamy historic homes. 

Many of the houses in Marblehead date back to 1725. The majority of the homes once belonged to fishermen, shipwrights, and sailors. 

I love going down Washington Street in Old Town. There are plenty of options for coffee, shopping, and art galleries. 

You can’t visit Marblehead without going to Castle Rock Park. This is a popular spot in Marblehead Neck to watch waves and ocean views from the cliffs. 

Head down Ocean Avenue to Castle Rock Lane to take in stunning views of the sea and a rugged coastline. There are steps to the left of the dramatic rocks that head down to a small beach with tidepools. You just might see a sea star!

Nantucket

An island off the coast of Cape Cod is best known for its whaling history and reputation as a summer getaway.

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Nantucket is an island south of Cape Cod that relishes in its isolation. A quintessential trip to Nantucket consists of riding through the cobblestone streets on bikes and relaxing along the shore with a beach read. 

Nantucket was the whaling capital of the world in the late 18th and early 19th centuries. The Nantucket Whaling Museum tells the story of how Nantucket left its mark on whaling history. The museum’s scenic rooftop is a big hit and the educational programs are popular.

Newburyport

A charming little seaside New England town in Northeastern Massachusetts. 

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Newburyport is about an hour’s drive from downtown Boston. This charming town along Massachusetts’ North Shore offers visitors iconic coastal views to explore. 

Wander around the Waterfront Park and boardwalk. There is no shortage of things to do here. Lounge on the grass or browse local shops. The Waterfront Park is especially nice during the spring and summer months.

Be sure to check out Oldies Marketplace, an antique store loved by locals and visitors alike. You will find furniture, decorations, jewelry, and clothes. There are tons of curious knick-knacks to look through.

Crane Estate, Ipswich, MA

This luxury summer home sits on 2,100 acres of land surrounded by stunning sea views.

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Crane Estate is a remarkable 19th-century home located in Ipswich, Massachusetts. This iconic summer estate is on the Eastern Seaboard, offering stellar views of the sea. 

Crane Estate was once the summer home of Chicago Tycoon Richard Crane and his family. The property is home to Crane Beach, Crane Wildlife Refuge, and Castle Hill — a mansion with 59 rooms.

Garden lovers can rejoice at Crane Estate. There are guided tours and self-guided tours to explore the Italian Garden, Rose Garden, and more of the property. You can hike through the beach, boardwalks, dunes, and marshes.

Fenway Park

Home to the Boston Red Sox and one of baseball’s most iconic ballparks.  

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Fenway Park is the oldest baseball stadium in Major League Baseball. It has been home to the Boston Red Sox baseball team for over a century. 

The park’s most iconic feature is known to locals as the Green Monster. It is a 37-foot wall painted in green, located in the left field. It houses the park’s scoreboard during games.

You should try to catch a game at Fenway even if you aren’t a diehard Red Sox Fan. It is a top Massachusetts attraction during baseball season (April to early October) and a fun experience overall.

Plum Island

A popular summer destination named for the beach plums that grow wild in its dunes.  

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Plum Island is a barrier beach island located in Northeastern Massachusetts. The island is only 11 miles long, but it’s packed with plenty of opportunities for fun and relaxation.

Head over to the Parker River National Wildlife Refuge. It has 4,662 acres of land that’s home to hundreds of species of birds, animals, and plants. The peaceful Parker River is perfect for cyclists and nature lovers, too. 

Check out the Plum Island Lighthouse. It was formerly known as the Newburyport Harbor Light. Occasional public tours of the lighthouse are available through the organization, Friends of Plum Island Light. The charming town of Newburyport is nearby.

Gloucester

America’s oldest fishing port with a rich maritime history.

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Gloucester is a popular summer destination when visiting Massachusetts. This charming and walkable city is brimming with history, culture, dining, shopping, and beaches. 

This seaside city is perfect for friends, families, and visitors of all ages. Gloucester is one of the best New England ports for whale watching. I recommend booking a tour with Cape Ann Whale Watch, as frequent tours are offered from mid-April through October. 

Another attraction I love in Gloucester is Hammond Castle Museum, a medieval-style castle. The inventor and art collector John Hays Hammond Jr. completed the castle in 1929. Here, you can see artwork and ancient artifacts on a self-guided walking tour.

Cape Cod

This famous Massachusetts summer destination is best known for its scenic, sandy beaches.

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Cape Cod has long been a popular New England summer destination. This hook-shaped island on the Atlantic Ocean is acclaimed for its beaches, seafood, and endless coastal fun. Just read Sami’s guide to Cape Cod activities to see what I mean!

Spend a day at the picturesque Race Point Beach. It is the perfect place for playing in the water, building sand castles, and hunting for seashells. Walk over to the Old Harbor Life-Saving Station Museum and learn about the history of the Coast Guard. 

Set aside an entire day to visit the Cape Cod National Seashore. Explore walking trails through salt marshes and see six beautiful beaches. Nature lovers will want to grab their binoculars. The Cape Cod National Seashore is home to many migratory seabirds. You can see them on a stroll through Fort Hill Trail. 

End your day with a relaxing evening at one of Cape Cod’s charming hotels.

📚 Related Reading: My off-season getaway at AutoCamp Cape Cod

Martha’s Vineyard

A charming New England island just a short ferry ride from Cape Cod.  

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Martha’s Vineyard is the best place to visit in Massachusetts for stunning natural beauty and scenic sandy beaches. There’s a vibrant beach culture here and it’s the perfect weekend getaway for relaxing by the sea. 

Martha’s Vineyard is dotted with charming small towns that make it feel special. Vineyard Haven is a busy port town that welcomes day-trippers to browse its array of local boutique shops. Oak Bluffs is a colorful small town with a Victorian boardwalk. I especially love the pizza and ice cream emporiums here.

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I hope this guide gave you plenty of options for places to visit in Massachusetts, whether it’s your first trip or not. For more ideas on places in Massachusetts, check out my list of the best day trips from Boston!