When you think of Massachusetts, what comes to mind first? Many people picture the historic sites and cobblestone streets of Boston. While Boston may be Massachusetts’ biggest city and a major cultural hub, the Bay State is filled with diverse experiences all over.
Over in Boston, you’ll find historical tours, music festivals, and landmarks like Fenway Park and Faneuil Hall. But not too far outside the city, you’ll discover even more to do, from the haunted hub that is Salem to the sun-filled beaches of Gloucester.
Over in Cape Cod, you’ll discover sights for a perfect family vacation. And in Martha’s Vineyard, you’ll find breathtaking views and upscale shopping and dining.
In Western Massachusetts, you’ll find even more to do, like riding a roller coaster through the Berkshires or spending a family-friendly day at a museum dedicated to our favorite children’s book characters.
Massachusetts is considered to have a humid continental climate, marked by cold winters and warm summers. So, many of the best things to do in Massachusetts are best done when the weather is warmer, especially if you’re looking for some days at the beach.
But that doesn’t mean visiting Massachusetts outside the spring and summer months can’t be fun and memorable. Some of the best Massachusetts attractions happen later in the year, like the Boston Book Festival and Salem’s Haunted Happenings, both of which occur in October.
With so many things to do in Massachusetts, it’s hard to know where to start. To help you plan your dream vacation to the Bay State, we’ve compiled our list of the absolute best things to do in Massachusetts.
If you follow these fun and unique Massachusetts bucket list recommendations – from hikes up to stunning views to one-of-a-kind museums to festivals that are true cultural celebrations – there’s no doubt you’ll have an amazing time exploring this historic state!
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25 Fun and Unique Things to do in Massachusetts
1. Take Part in Salem’s Haunted Happenings
Is there another city that’s quite as synonymous with Halloween as Salem? Salem is one of the best places to spend the spooky season in the United States. Although this time is also Salem’s busiest, it’s worth braving the crowds to check out the area’s famous Haunted Happenings. Since 1982, the Salem Chamber of Commerce and the Salem Witch Museum have been inviting Halloween lovers to Salem throughout October for the city’s Haunted Happenings.
Throughout the month, guests are invited into terrifying haunted houses, on tours celebrating the spookiest sides of Salem, to don their witchy best for costume balls, and so much more. You’ll find something for everyone at this event, from family-friendly festivals to haunted houses that would scare the pants off even the biggest thrill seeker.
But Haunted Happenings is about more than Halloween. It’s a memorial to Salem’s history and a celebration of its culture. Learn about the true story of the witches of Salem, meet psychics who want to aid you on a spiritual journey, and step into the past in special events held in the area’s many museums.
2. Explore Shelburne Falls
Located in northwest Massachusetts, the historic village of Shelburne Falls is home to some of the most beautiful sights in Massachusetts. You’ll love getting out in the great outdoors here and taking in the incredible views.
One of the top attractions is the aptly-named Bridge of Flowers. Once a trolley bridge, it now houses a stunning garden filled with flowers planted by the Shelburne Falls Area Women’s Club. Take a walk over the bridge anytime between April and October, when the bridge is open to visitors and the flowers are in bloom.
Another beautiful sight can be found at Salmon Falls. From the viewing platform, you’ll take in the crystal-clear water as it cascades down while the colorful village, lush trees, and green mountains sit in the background.
Inside Shelburne Falls itself, you’ll find a lively art community. Be sure to keep an eye out for the mosaic murals scattered throughout the village.
3. Go for a Sail around Gloucester
The Schooner Thomas E. Lannon has been a part of Gloucester’s history since 1997, but its origins date back further than that. The boat is named after the owner, Tom Ellis’ maternal grandfather, who fished out of Gloucester from 1901 to 1943.
The Schooner Lannon was designed to make you feel like you were sailing on a fishing schooner a hundred years ago. Gloucester’s fishing history is something that the residents are deeply proud of, so you can guarantee an authentically wonderful time at sea.
Today, the boat offers two-hour sails and private charters from mid-May to mid-October. When you climb aboard, you’ll be delighted by the views of Gloucester’s working harbor and the rocky coastline.
You’ll take in lighthouses, beautiful beaches, and even historic castles. Unlike some other boat tours, this isn’t designed to be an educational journey. There’s no narrator on board. Instead, it’s just meant to be a peaceful cruise where you can be at one with the sea.
In addition to the standard cruises, there are also featured events throughout the year. Dance on the water with the Sunset Music Cruises. Or enjoy the atmosphere on a Moonlight or Stargazing Sail. If you’re visiting around the Fourth of July or during Labor Day weekend, you can join for a dessert cruise and take in the show during the Fireworks Sails.
There’s also one very special sail that happens during the Gloucester Schooner Festival Race, which is held every Labor Day weekend. The Schooner Lannon always participates in this race, and you’re invited on board. Cheer on your captain as you take in the one-of-a-kind views.
4. Board a Swan Boat at the Boston Public Garden
The Boston Public Garden is one of the most beautiful sights in Massachusetts, and there’s no better time to visit than in the spring when the Swan Boats are back on the lagoon. The story of the Swan Boats dates all the way back to the 1800s. Guests have long loved spending spring and summer out on these iconic boats.
These boats take you on a scenic tour of the lagoon, giving you a chance to lay back and relax as you cruise around. The ride lasts approximately 12 to 15 minutes, moving at a leisurely pace through the water. The boats typically arrive back on the water in early spring and depart for the season in early fall. If you’re visiting Massachusetts through the spring and summer, taking a Swan Boat ride is a great way to get in some Massachusetts sightseeing.
5. See a Game at Fenway Park
Fenway Park is more than a baseball field. It’s a true piece of history and an experience all its own. And seeing a game at Fenway Park is easily one of the top things to do in Massachusetts.
Baseball season typically lasts from spring to fall, so you’ll only be able to catch a game if your Massachusetts trip happens within those seasons. But that doesn’t mean that you can’t experience the magic of this historic park if you visit in the winter.
Public tours of the park are available all year round. You may also catch other events, like concerts, happening at Fenway, although these typically occur in the summer.
6. Take a Ghost Tour through Salem
With Salem’s rich history, it’s no surprise it’s considered one of the most haunted spots in America. That’s why going on a ghost tour through historic Salem is one of the coolest things to do in Massachusetts. There are many to choose from, but Salem Ghosts is one of the best, as it takes you to the locations of some of the lesser-known dark tales in Witch City.
With Salem Ghosts, you meet Mr. Derby, a once-prominent merchant whose specter is rumored to haunt Old Town Hall. You’ll learn about the sordid story of what happened in what’s now the basement of Wicked Good Books. You’ll hear the tragic tale of Abigale Ropes, whose angry spirit terrorizes the famous Ropes Mansion, which you may remember from the beloved cult classic Hocus Pocus.
7. Take a DUCK Tour through Boston
Riding on a DUCK, an authentic World War II amphibious vehicle, through Boston is one of the top things to do in Massachusetts. This unique tour will take you through this historic city and around its many landmarks, from the Old State House to the iconic “Cheers” bar. Your guides, the ConDUCKtors, are knowledgeable about all things Boston and will tell you little-known facts you won’t find anywhere else.
While the tour would be impressive enough, the real reason you want to take a Duck Tour and not another driving or walking tour comes at the end. Since you’re in an amphibious vehicle, it only makes sense to put it to use. Be prepared to splash down in the Charles River in your DUCK, where you’ll get one heck of a view of the Boston skyline.
Because of Boston’s climate, the DUCKs don’t run all year round. They typically operate between early spring and early November. But if you are visiting within those months, this tour is one that needs to be on your Massachusetts bucket list!
8. Shop and Dine around Faneuil Hall
Step back in time when you visit Faneuil Hall, a historic area that has served as a meeting hall and marketplace for more than 270 years. Stroll along the cobblestone street and take in the history of this cultural hub. Venture through Faneuil Hall Marketplace, also known as Quincy Market, to discover tons of shops, restaurants, and stalls.
From shops with handmade Christmas ornaments to spice shops, there’s something for everyone at this fun location. If you’re looking for an iconic Boston treat, grab yourself a bowl of New England clam chowder from Boston Chowda Co. or indulge in a lobster roll from Wicked Lobstah. Finish off your meal with some melt-in-your-mouth cookies from The Boston Chipyard.
9. Have Your Fortune Read at Crow Haven Corner
Salem is a haven for those who believe in a world beyond our own. If you’re a true believer in all things magical and mystical, you’ll love meeting Lorelei, Salem’s famous love clairvoyant. You’ll find her at Crow Haven Corner, the oldest witch shop in Salem.
Having your fortune read by Lorelei is easily one of the most unique things to do in Massachusetts. She’s been practicing her craft for over 35 years and is a true Salem staple.
When you do a reading with Lorelei, she’ll conduct a witch’s circle with you before she reads your tarot cards and your palm, does a health scan, and crafts a spell to help you manifest whatever you may need in life. Lorelei doesn’t guarantee mediumship, but she’s been known to speak to loved ones in the great beyond in some readings.
As a bonus for animal lovers, Lorelei, who runs a nonprofit called Salem Saves Animals, will always have her dogs with her for every reading. If you’d like to book a reading, walk-ins are welcome, but especially if you’re visiting around Halloween, you should make a reservation in advance.
10. Take in the Art at the Isabella Stewart Gardner Museum
Boston is home to many museums, from the Museum of Fine Arts to the Museum of Science. But one of the more hidden gems is the Isabella Stewart Gardner Museum, a museum where the location itself is nearly as gorgeous as the art it houses.
This art museum is styled as a Venetian palace and is surrounded by beautifully-maintained lush greenery. Inside, you’ll find a diverse collection of American, Asian, and European art. The museum’s namesake and creator was born a New York City socialite, but she called Boston her home when she relocated to the city with her Boston-born husband.
Isabella collected art throughout her life and devoted herself to filling the museum with art from around the world. Today, you can find more than 7,500 paintings, sculptures, furniture, textiles, silver, and ceramics within the walls of the museum, as well as 3,000 rare books and 7,000 archival objects.
11. See a Show in Boston’s Theater District
Boston’s Theater District is one of the best places to spend an evening in Massachusetts. This area is filled with plenty of options to see a show. No matter when you visit, you’re sure to find something in one of the theaters that piques your interest.
The Boston Opera House is one such great option. It’s an ornate theater where you can see spectacular productions of touring Broadway shows. At the Colonial Theatre, owned by Emerson College, you can often see shows before they premiere on Broadway. The Wang Theatre, which was designed to look like the Paris Opera House, is where you want to head if you want to see touring comedians, singers, and much more.
One recommendation for spending an evening in the Theater District: Grab a bite to eat first at the Omni Parker House, a famous hotel that’s home to the original Boston Cream Pie. It’s an easy walk to any of these theaters from the hotel, and getting a Boston Cream Pie is a must-do thing to do in Massachusetts.
12. Visit Gloucester During St. Peter’s Fiesta
Gloucester has a passionate Italian American community, which is responsible for the creation of St. Peter’s Fiesta, held for five days every June. It’s a celebration of Gloucester’s fishing history and faith.
St. Peter is the patron saint of all fishermen and was considered the Catholic Church’s first pope. Gloucester has a long history as a fishing hub, a history that’s greatly celebrated by the town’s residents.
This family-friendly festival is filled with all kinds of entertainment for every age. Watch the community parade through the city streets with statues honoring their heritage. See the commercial fishing fleet be blessed.
During the annual Seine Boat Race, root for the Nina, the Pinta, or the Santa Maria. Take part in the Fiesta 5K. And take your kids to performances of storybooks that come to life that are focused on Gloucester’s storied history.
But likely the highlight of the festival is the annual Greasy Pole competition, which is guaranteed to get your heart racing. This unique contest takes place 200 feet off Pavilion Beach, where a 45-foot telephone pole is attached to a platform and extended out over the water, with a red flag nailed to the end. Then, the pole is greased. One by one, the contestants do their best to contend with the tricky pole as they fight to be the one to capture the flag!
13. Celebrate Literature at the Boston Book Festival
If you’re a book lover, there’s perhaps no better way to spend a day in Massachusetts than at the Boston Book Festival. This annual event typically happens every October in Copley Square. The guest list of speakers is always stacked with talented writers, authors, journalists, historians, and illustrators from all genres. Previous speakers include Margaret Atwood, Lemony Snicket, and Ken Burns.
You’ll be able to meet your favorite authors, discover new talent, and learn all about the craft of writing. But the location of the Boston Book Festival is another reason why it’s one of the must-do things in Massachusetts.
Copley Square is filled with historic buildings that are true architectural marvels. And attending these events allows you to step into the buildings and get an even better look at their beauty. From the massive Romanesque Trinity Church to the stunning Gothic Old South Church, you’ll be sitting inside historical landmarks as you listen to your favorite writers talk about their craft.
14. See a Movie at the Wellfleet Drive-In Theatre
In Cape Cod, you’ll find another piece of history: the Wellfleet Drive-In Theatre. Visiting the Wellfleet Drive-In Theatre is one of the coolest things to do in Massachusetts if you’re a movie lover!
Originally opened in 1957, this movie theatre is the last of its kind in Cape Cod and one of only about 300 drive-ins left in the US. Although Wellfleet has an indoor cinema for movies all year round, the drive-in is only open during the summer. If you’re taking your Massachusetts trip in the summer, be sure to stop by this iconic location for a traditional double feature.
Pack some blankets, pick up some snacks from the concession stand, and tune into 89.5FM. Then, sit back and snuggle with your sweetheart under the stars.
15. Play at the Amazing World of Dr. Seuss Museum
Over in Springfield is a one-of-a-kind museum and one of the best things to do in Massachusetts if you’re traveling with kids. The Amazing World of Dr. Seuss Museum celebrates Springfield native Theodor Geisel, better known as the great Dr. Seuss.
This interactive museum puts you and your little ones right in the middle of Dr. Seuss’s beloved stories. The first floor is fully bilingual, with every exhibit in Spanish and English. Here you’ll find tales of Dr. Seuss’s Springfield roots and plenty of opportunities for educational fun.
Just don’t be surprised when your little ones leave here and can’t stop rhyming. You’ll recycle with the Lorax, have a ball down in Whoville with the Grinch, and make some art with the Cat in the Hat.
The second floor is curated by Dr. Seuss’s two stepdaughters and great nephew. It features a recreation of his studio and living room, letters, family photographs, and never-before-seen artwork.
16. Ride the Thunderbolt Mountain Coaster
Over in the mountains of Western Massachusetts, you’ll find the Berkshire East Mountain Resort, which plays host to one of the most unique things to do in Massachusetts. Have you ever wanted to race through the great outdoors and take in its beauty on a thrilling adventure? You can with the Thunderbolt Mountain Coaster.
As the only mountain coaster in Massachusetts and one of the longest mountain coasters in North America, this track takes you through the forest and up 1,580 feet to the top of the mountain. Then, the cart disengages, and gravity does the work of creating one incredible ride.
Your ride will reach up to 25 miles per hour as you meet loops and twists on your way down. Expect breathtaking views throughout your entire seven-minute journey.
17. Visit Plymouth Rock
When the Pilgrims landed on Plymouth Rock, they created what would be the first successful European colony in New England. Seeing Plymouth Rock is a must-do thing to do for any history buff spending time in Massachusetts. But there’s more to the area than just seeing the famous rock.
Plymouth is filled with learning opportunities and places to immerse yourself in the past. Over at the Plimoth Patuxet Museums, you can learn about the Native people of the area and see how they lived.
Or you can step into a recreation of a farming and maritime village that the Pilgrims would have created. You can even see the Mayflower II, a full-scale recreation of the ship the Pilgrims arrived on.
Another place to step into the past is the Pilgrim Hall Museum, which houses an unmatched collection of artifacts from the Pilgrims. These museums typically close for the winter, but they open for special events. Be sure to keep an eye on their schedules leading up to your trip.
18. Kayak Around Edgartown Great Pond
Located on the South Shore of Martha’s Vineyard, the Edgartown Great Pond is a scenic spot that’s perfect for a kayaking trip. Paddle your way around the pond and take in the views. It’s quiet and ideal for a leisurely way of spending the day winding through the water.
When you’re done paddling, lay out on the beaches or take a stroll through the sand. Visiting in the evening will give you a chance to see spectacular sunsets over the water.
The town of Edgartown itself is also worth a visit. The charming, picturesque downtown is filled with boutiques, fine dining spots, and historic architecture.
19. Take in the View at the Aquinnah Cliffs
The Aquinnah Cliffs is another Martha’s Vineyard spot that’s one of the best spots for Massachusetts sightseeing. These clay cliffs were carved by glaciers millions of years ago. Today, they’re an incredible place to take in the view.
You can see the cliffs up close from the beach paths. Or you can take the upper trails to the top of the cliffs to take in the panorama and see the nearby Elizabeth Islands.
These stunning cliffs are alive with color, from the rainbow of wildflowers to the red, orange, and gold cliff facade. Taking these trails in the evening is especially beautiful as these colors are illuminated by the setting sun. If you’re a photographer, you’ll truly adore golden hour here.
20. Enjoy the Music at Tanglewood
Nestled on 500 acres between Lenox and Stockbridge is Tanglewood, the summer home of the Boston Symphony Orchestra. If you’re visiting Massachusetts in the summer, seeing Tanglewood is one of the most unique things to do.
Here you’ll find the Tanglewood Music Center, the training academy for both the Boston Symphony Orchestra and the Boston Pops. Throughout the summer, you’ll discover a festival of music, from performances from these incredible talents to recitals from those honing their craft to seminars from some of the most amazing musicians in the world. If you’re a lover of classical music, Tanglewood is a can’t-miss experience.
21. Explore the Norman Rockwell Museum
Over in Stockbridge is a celebration of American art. Built on a scenic 36-acre campus, the Norman Rockwell Museum showcases the magnificence of his paintings and illustrations. Travel through 10 galleries with constantly-changing exhibits, ensuring that every time you visit is a totally new experience.
Though the museum is named in Rockwell’s honor and primarily showcases his work, the museum is dedicated to the art of illustrations in general. You’ll also find exhibits with artwork from illustrators from all over, such as an exhibit focused on the children’s book character Eloise, created by Hilary Knight.
The history of illustrations is deeply tied to our history, as they often featured social commentary and a celebration of our way of life. In many ways, this museum is as much a historical museum as it is an art museum. It’s a perfect way to spend a day in Massachusetts if you’re a lover of history, art, or both.
22. Be at One with Nature at Walden Pond
In Concord, you’ll find perhaps one of the most famous ponds in the US. Walden Pond is best known as the inspiration behind Henry David Thoreau’s Walden. The book focused on Thoreau’s spiritual self-discovery upon living in the area’s natural beauty. And we can still learn quite a bit from experiencing the stunning surroundings here.
Walden Pond is an ideal place for a peaceful stroll or perhaps even simply meditating on its banks. It’s a place that’s deeply tied to self-reflection. When you spend a day here, you’ll leave more refreshed and grateful to have been surrounded by such a calming environment.
During the summer, you can cool off in the pond and go for a swim, or you can pack a picnic to relax in the sun. While you’re at Walden Pond, be sure to stop by the replica of Thoreau’s single-room cabin.
23. Go Whale Watching in Gloucester
Gloucester is a wonderful place to spend a day at the beach or out on the water. And if you decide to get out on that clear blue sea, you just might spot some stunning creatures alongside your vessel. You can see whales anytime from May to October, but whale-watching boat captains in the area say that September may be the best month for sightings.
What can you expect to see? According to Cape Ann Whale Watch, the most commonly spotted creatures are humpback whales, fin whales, minke whales, Atlantic white-sided dolphins, northern right whales, and harbor porpoises. Sei whales, blue whales, sperm whales, and long-finned pilot whales have also been spotted on occasion.
When you take a whale-watching tour with a company like Cape Ann Whale Watch, you’ll be led by naturalists with decades of experience who can take you to the top spots to see whales. Going whale watching in Gloucester is one of the best ways to do some Massachusetts sightseeing.
24. Visit the Animals at the New England Aquarium
Over by the Boston Harbor is one of the top things to do in Massachusetts: the New England Aquarium. This aquarium, which is dedicated to conservation and using innovative solutions to solve threats to ocean life, is filled with opportunities for fun and education.
Study the African and southern rockhopper penguins at the Penguin Colony. See the California sea lions play at the New Balance Foundation Marine Mammal Center. Or immerse yourself in the colorful beauty of the Indo-Pacific Coral Reef.
Over in the Simons Theatre, you can sit back and relax while you take in a 3D show on a projection screen that’s more than six stories high. The aquarium also partners up with Boston Harbor City Cruises to allow you to get joint tickets to visit the New England Aquarium and take a whale-watching cruise.
From finback whales to white-sided dolphins, marine life is abundant in this area, so you’re guaranteed to spot something. And if you don’t, Boston Harbor City Cruises will give you a free ticket to visit another time.
25. Get Your Tickets for the Boston Calling Music Festival
Since 2013, Boston Calling has been a staple in Boston. Boston Calling typically happens in May, taking over the Harvard Athletic Complex. The three-day festival is filled with beloved bands and artists. Some previous highlights include the Foo Fighters, Alanis Morissette, and Paramore. But across the three days, expect over 50 acts to perform.
This massive festival also features tons of dining options courtesy of many of Boston’s best food vendors. If you’re a music lover, going to Boston Calling is one of the top things to do in Massachusetts and a must-do experience!
There you have it! The 25 best things to do in Massachusetts. What’s your favorite thing to do in the Bay State?
Planning a trip to Massachusetts? Check out our favorite books and travel guides!
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