Massachusetts Travel Guide: Where to Go, Things to Do & When to Visit

Home of the illustrious Harvard University and the first library in America, Massachusetts absolutely teems with possibilities for tourists. Every year, millions of travelers flock to this Northeastern U.S. state where lush foliage meets the sea. This year, you, too, should head to one of the many destinations that exude this unique brand of New England charm!

The coastal state of Massachusetts offers many different types of vacations, from sophisticated seaside getaways in Nantucket to a fall escape in cozy inland towns in the Berkshires. No matter what type of traveler you are or what kind of holiday you’re craving, Massachusetts has a destination that’s perfect for you.

Buzzing with excitement about your upcoming trip to Massachusetts? By the time you’re done with this complete Massachusetts travel guide, you’ll be ready to fill your itinerary, pack your bags, and jet set as soon as possible!

Looking to explore other destinations in the USA? Check out our United States Travel Guide for more destination ideas & tips!

Why Treksplorer? Founded in 2011 by Ryan O’Rourke, Treksplorer provides travel recommendations and advice to millions of readers every year. Our content is rooted in our writers’ firsthand experiences, in-depth research, and/or collaborations with other experts and locals. Read more about our editorial policy.

Where to go in Massachusetts

Boston

All certified city slickers need to have Boston on their travel bucket list. Known for its gorgeous skylines laden with skyscrapers, bright lights, and all that jazz, this coastal city will impress even the pickiest tourist. Witnessing world-class entertainment and chowing down on critically acclaimed food is just the beginning of what you can see and do.

Still need convincing? Boston promises an experience steeped in history and highlighted by a vibrant arts scene. From the best fine arts museum in America to a penchant for live theatre, the capital of Massachusetts is a hotspot for all artistic pursuits. Be sure to check out one of the 58 museums before you leave town!

Of course, sports fanatics love Boston, too. You can take your family out to a ballgame at Fenway Park, browse the Sports Museum, or score some tickets to NHL, NBA, or NFL games during their respective seasons.

Ready to plan your trip to Boston? Get started with these travel resources from our Boston Travel Guide…

Cape Cod

Colorful, historic, and famous for its grassy beach dunes, Cape Cod is a maritime destination that everyone must visit at least once. And let’s not forget the seafood! In Cape Cod, you’ll get a true taste of New England with dishes like fried clams and decadent lobster on nearly every menu.

Though Cape Cod is quite family-friendly, there are a few adult attractions, from vineyards and breweries, making celebrating happy hour a breeze. If you do have your little ones along, be sure to head to the cranberry bogs, where you can wade around and harvest some of these red beauties for yourselves. It’s a memory that will last a lifetime!

Cape Cod is a great choice for ocean lovers and busybodies, as it’s full to the brim with aquatic activities. When you’re done making a splash at the local beaches, you may want to experience the sea in a different way by learning to sail or heading out on a whale-watching boat. (Just be sure to bundle up because it can get quite cold out there on the open ocean!)

After the sun has set, head on over to the sandwich salt marshes for a brilliant display of bioluminescence. It isn’t every day you get to witness this incredible natural phenomenon—this isn’t an activity you’ll want to miss!

Ready to plan your trip to Cape Cod? Get started with these travel resources…

Nantucket

A popular choice for girls’ weekends and romantic holidays, Nantucket is the island escape of your dreams. It’s much quieter than Cape Cod so if you’re looking for some slow living by the seaside, you’ve found it.

Reminiscent of the Hamptons, Nantucket is known for its Saltbox houses donning cedar shakes and hydrangea gardens in full bloom. How beautiful!

So, what does a holiday in Nantucket look like? For starters, you’ll have your pick of dreamy beach houses to rent, or you can stay at a classy boutique hotel. From there, you can collect seashells on a morning stroll and curl up with a good book in the powdery sand.

Maybe you’ll even cast a line from shore and try your hand at ocean fishing in the waves. Then, as the day comes to a close, you’ll settle back in at night with a beach bonfire and a clam bake.

Though getting some much-needed R&R is at the heart of everything in Nantucket, there are also a few more touristy things to do here. On a day when you’re feeling more adventurous, you may choose to explore the local lighthouses, walk the seashell trail at Sconsett Bluffs, or rent some cruiser/beach bikes with wicker baskets for a jaunt around the island.

Martha’s Vineyard

Despite its name, there aren’t any grapevines in Martha’s Vineyard. But this popular Massachusetts island destination still has tons to offer. Martha’s Vineyard comprises six towns, and if you have the time, it’s worth visiting all of them!

Martha’s Vineyard is a naturalist’s dream. Long boardwalks sweep through the marshes and along the shoreline. It’s a hotspot for birding, so be sure to keep your eye open for gentle giants like herons and ospreys. You can also hike down the pathways above and below the Gay Head Cliffs, Martha’s Vineyard’s top attraction.

More of a beach bum? Spend your day beach-hopping your way from shore to shore, taking in the postcard-perfect sugary white sand and turquoise waters. Even adrenaline junkies can get their thrills by bridge jumping off Jaws Bridge, which made its big-screen debut in JAWS.

Looking for a touch of whimsy? Parts of Martha’s vineyard are downright fairytale-esque. The streets are lined with colorful “gingerbread houses.” There’s even a Flying Horses Carousel for kids and adults to ride!

Salem

Looking for a trip to celebrate the spooky season? You can’t do better than Salem. Known for the Salem Witch Trials and its complicated maritime history, this Massachusetts destination is the perfect place to explore around Halloween and embrace your darker side.

True to its past, Salem has a wide range of themed attractions, including the Salem Witch Museum, filming locations from Hocus Pocus, witchy-themed shops, and ghost tours—you know, the works!

Of course, a good haunt isn’t the only thing that Salem has to offer. A stroll down the sidewalk presents the opportunity to admire the gorgeous historical architecture. A trip down the harbor for an afternoon sail is always a good idea, too.

Looking to up the ante a little bit? Head to Bit Bar, a boozy arcade and cocktail lounge where you can indulge your inner child.

The Berkshires

For a vacation that brings all the autumnal vibes, The Berkshires are a home run. Especially popular during the colder months of the year, this quaint destination is chalked full of upscale bed and breakfasts, cute independent shops, and farm-to-table cafes. Even if it’s just for a relaxing fall drive as your passing through, this Massachusetts gem is one you won’t want to miss.

The Berkshires also have a certain outdoorsy appeal. Pull on your hat, scarf, and flannel and strap on your backpack; it’s about to be a wild ride.

If you can brave a little chill in the air, you’ll have over 400 hiking trails to choose from that light up with sunset hues in the fall. Another popular way to enjoy the Massachusetts wilderness is an early morning paddle. (Can’t you just imagine your canoe slicing through the lake?)

If you’re a bonafide bookworm, you’ll adore the literary feel of The Berkshires. After all, this is the kind of place people write novels about.

After spending hours perusing the shelves of the many used bookstores, you’ll want to amble up to The Mount, the historic estate of Edith Wharton, where she wrote several of her books.

Other destinations in Massachusetts

Provincetown
Cambridge
Plymouth
Worcester
Hyannis
Amherst
Newburyport
New Bedford

When to visit Massachusetts

The best time to visit Massachusetts is from the beginning of September to the end of October. In these fall months, the temperatures are moderate. Even beachgoing is still an option in the September sun. As an added bonus, during these months, Massachusetts comes alive with fall colors.

All that being said, Massachusetts is a fabulous all-season destination. You’ll find plenty of things to see & do whether you visit in the spring, summer, autumn, or winter.

In fact, you may want to make your decision based solely on your weather preferences. The colder months can be quite treacherous, but they’re also accented by pretty snow-covered landscapes and cozy Christmas pastimes.

How to get to Massachusetts

By air

Massachusetts is home to seven major commercial airports. Most travelers flying into Massachusetts will likely arrive via Boston Logan International Airport (BOS). Several major airlines fly into BOS from other U.S domestic gateways, including:

American Airlines
American Eagle
Delta Air Lines
JetBlue
Southwest Airlines
Spirit Airlines
United Airlines

By road

Massachusetts is well-connected to the neighboring states of Connecticut, Rhode Island, New York, Vermont, and New Hampshire. Popular road routes into Boston and approximate driving times include:

Hartford, CT (1h47m)
Providence, RI (1h6m)
New York City, NY (4h42m)
Burlington, VT (3h38m)
Portsmouth, NH (1h15m)