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New England: 14 Unique Places And Things To Do In Massachusetts

New England: 14 unique places and things to do in Massachusetts

The states of New England include Massachusetts, New Hampshire, Maine, Vermont, Connecticut, and Rhode Island. Each is unique, and it’s pretty easy to spend days or weeks there. Vermont has its syrup, Maine has its shoreline, and New Hampshire has its White Mountains. Nevertheless, Massachusetts has a lot of history, delicious food, and many places that will leave you breathless. In this article, you will find 14 of the best places and things to do in Massachusetts.

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Massachusetts – Ressources & Recommendations

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Are you ready to travel to Massachusetts, New England? No matter if during Indian Summer or whenever else. Massachusetts is fun year round. From Boston, Cape Cod, Cape Ann, Salem, or the Berkshires. For solo traveler or families. This will be the road trip of your lifetime! #travel #indiansummer #newengland #massachusetts #thingstodo

The North

1. Boston

Walking the Freedom Trail is the best way to get to know Boston. Begin at the Boston Common, the city’s green lung, and finish at the Bunker Hill Monument, where the first major battle of the American Revolution took place. You cannot miss the route because a red brick line is embedded on the city’s sidewalks, leading to 16 major historical sites and marking this 2.5-mile route. You will find some handouts with all the essential information at the tourist or central station. You can also attend one of the walking tours and listen to the guide. With the right timing, you can watch the cannonball fired by the USS Constitution around sunset.

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2. Cambridge, the university city

Just a short drive from Boston, you will find Cambridge, the home of two of the most famous elite universities. Harvard University and the Massachusetts Institute of Technology. If you like, you can take part in a walking tour of the university* area and experience campus life, or you can explore Harvard and Cambridge by yourself.

When I visited, I had mixed feelings. On the one side, I was impressed that I walked across the campus of such an elite university; on the other hand, I was also slightly disappointed. I still cannot describe exactly why; maybe, in my imagination, everything looked so much bigger. Sometimes, things seem to be shinier than they are in reality.

Are you ready to travel to Massachusetts, New England? No matter if during Indian Summer or whenever else. Massachusetts is fun year round. From Boston, Cape Cod, Cape Ann, Salem, or the Berkshires. For solo traveler or families. This will be the road trip of your lifetime! #travel #indiansummer #newengland #massachusetts #thingstodo

3. Cape Ann

It will be a 45-minute car ride from Boston to Gloucester, which I recommend as a home base for the next two or three days. From here, you can go to Rockport, Halibut State Park, Salem*, and Gloucester itself.

The best hotel for your stay would be the Atlantis Oceanfront Inn* in Gloucester. Whenever I return to that area, I will stay there again. It has a beautiful ocean view from each room, the most beautiful sunrises I have seen, and the rooms, the service, and the breakfast are extraordinary.


Start your day by watching some whales and maritime animals with the 7 Seas Whale Watch at Gloucester. Just in case, prepare yourself with some medicine against seasickness. The sea can be very rough, and if your stomach is not used to it, you might get problems. You can also ask the crew in an “emergency.”

Afterward, explore Gloucester and visit Rockport. Shop around Bearskin Neck and enjoy Motif #1. Do not forget the beaches. Continue to Halibut State Park and walk alongside the old granite quarry and the shores.

Indian Summer-New England-Massachusetts-Cape Ann-Gloucester-Whale Watching #indiansummer #newengland #massachusetts #capeann #gloucester #whalewatching Indian Summer-New England-Massachusetts-Cape Ann-Rockport-Motif #1 #travel #indiansummer #newengland #capeann #rockport #motif1 Indian Summer-New England-Massachusetts-Cape Ann-Halibut State Park #travel #indiansummer #newengland #massachusetts #capeann #halibutstatepark Indian Summer-New England-Massachusetts-Cape Ann-Rockport #travel #indiansummer #newengland #massachusetts #capeann #rockport #thingstodo

4. Salem

Since 1626, when the first settlers arrived in Salem, many people have come to visit and mostly want only one thing: Witches! As it is probably best known for the witchcraft trials in 1692, this colorful coastal city has more to offer, such as a rich maritime heritage, historic architecture, and many stories from almost four centuries.

Take a ride with the fully narrated Salem Trolley Tour for a first overview. It brings you to all the essential attractions in one hour, and you can hop on and off whenever you want. Visit the Salem Witch Museum, the Old Burying Point, the Salem Witch Trials Memorial, or the Salem Pioneer Village.

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The best time or, better, most exceptional time to visit Salem is probably Halloween. The whole city goes crazy, and there are extra Halloween specials, such as the show at the Gallows Hill Museum & Theater or the annual Hawthorne Hotel Halloween Party.

When I visited Salem, I missed Halloween by about a few days, but the preparations for this day were already underway, and I could feel that it was a special time for the city and its people. Maybe it is an excellent reason to go back one time.

By the way, do you want to visit the Salem Witch Museum*? You can save some money by using the Boston Go City Card*

5. Lexington & Concord

If you cannot get enough of history, even if you have already walked the freedom trail in Boston, Lexington and Concord are the places to be for you. About half an hour from Boston, you will find the birthplace of American Liberty! Take a tour of Concord! Ride along the historic Battle Road* and learn everything about the legacy of the events from April 19, 1775. It started at the Lexington Battle Green, where the outnumbered Lexington militia confronted the British army, and ended up at the North Bridge, where colonial militiamen fired upon British Regulars.

The South

6. Plymouth

Right between Boston and Cape Cod, you will find Plymouth, where everything began. 1620, the first settlers landed here at the iconic landmark Plymouth Rock. The Pilgrims arrived on the Mayflower and established New England.

Today, you can experience history at the Plimouth Plantation, a fully functioning village, and an open-air museum. Learn how the settlers lived in the old days. Costumed actors behave as in former times. They cook, eat, and feed the animals, everything as they did in the settlement era. Even the Mayflower II, a reproduction of the original Mayflower, is usually on display.

7. Cape Cod

From Boston, you need a good hour by car, or you can make a Canal Cruise*.

Cape Cod, like Cape Ann, has a lot to offer. From visiting and strolling around Provincetown to hiking the Cape Cod National Seashore, you can enjoy the beautiful beaches with their massive dunes on one side and the Atlantic Ocean on the other.

Are you ready to travel to Massachusetts, New England? No matter if during Indian Summer or whenever else. Massachusetts is fun year round. From Boston, Cape Cod, Cape Ann, Salem, or the Berkshires. For solo traveler or families. This will be the road trip of your lifetime! #travel #indiansummer #newengland #massachusetts #thingstodo

Once you get hungry, try the fried mussels, which are available everywhere, or eat at the Lobster Pot in Provincetown, which a fellow traveler recommended.

8. Martha´s Vineyard

From Cape Cod, Hyannis, in particular, takes the ferry to Martha´s Vineyard, where many famous and rich spend their summer vacation. Discover the picturesque and beautiful gingerbread houses in Oak Bluffs or the New England flair with the grey wooden buildings, white churches, and fences in Edgartown. Rent a bike, explore the island, and enjoy the sunset while taking the day’s last ferry.

9. Nantucket

Another day trip to one of the nearby islands, Nantucket. A ferry to Nantucket is also available from Hyannis. Gay Point Lighthouse, the first and oldest one of the islands, welcomes you when you arrive at the port of Nantucket. When strolling through the historic old town, it is obvious why Nantucket’s nickname is “Little Grey Lady.” Most houses have grey wooden faces, and you will find cobbled stone streets, which is rare in the USA. Like Martha´s Vineyard, you can rent a bike and explore the rest of the island. But be aware of the contrary winds and the up- and downhills.

The West

10. Springfield

If you’re a fan of amusement parks, you’re right at Springfield. Six Flags New England is located just a short drive outside of Springfield. Are you a shopping fan? No problem, either! Springfield is known for its massive shopping center and outlets. And, of course, the Naismith Memorial Basketball Hall of Fame awaits you, too.

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11. Chesterfield Gorge State Forest

A bit more western than Springfield, nature enthusiasts will love the Chesterfield Gorge State Park. Hike alongside the gorge and enjoy rushing waters and scenic views. More activities, like hiking, cycling, skiing, fishing, hunting, and camping are possible. Everything you need when you want to be one with nature. Notably, while fall foliage, this must be a kind of magic.

12. The Berkshires

The Berkshire Hills expand from the borders to Vermont in the North, New York in the West, and Connecticut in the South, and are the home of the highest mountain (1095 m) in Massachusetts, Mount Greylock. They include the valleys of the Green, Hoosic, and Housatonic Rivers and have sprinkling lakes and ponds.

It’s no wonder that they are best known as a vacation destination with many outdoor activities, foliage viewing possibilities, a farm-to-table food scene, and flourishing arts institutions. The tourism industry in this area is mainly based on music, arts, and recreation. So, if you want to relax for a few days in nature, this might be the right place for you.

And if you miss the big city, no worries! You are back in Boston, New York City, or Albany in less than three hours.

Pin it!

Are you ready to travel to Massachusetts, New England? No matter if during Indian Summer or whenever else. Massachusetts is fun year round. From Boston, Cape Cod, Cape Ann, Salem, or the Berkshires. For solo traveler or families. This will be the road trip of your lifetime! #travel #indiansummer #newengland #massachusetts #thingstodo

13. Bash Bish Falls State Park

Do you like waterfalls? The Bash Bish Falls is the highest single-drop waterfall in Massachusetts. If you made it here, you are about two and a half hours west of Boston and almost in the neighboring state of New York. Hiking, picnicking, exploring the nearby Mt. Washington State Park, or visiting the Taconic State Park by crossing the border to New York. It is a paradise for nature lovers. 

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14. Mohawk Trail

The Mohawk Trail is the first scenic road in New England, and it opened in 1914. It consists of 50,000 acres of state parks and forests and is a great vacation alternative. Notably, during the time of the “Indian Summer,” you will find breathtaking views and opportunities to watch the fall foliage.

The trail follows a historic Native American footpath that connected Connecticut and Hudson River Valleys. Today, it is part of the U.S. 2, one of the oldest highways of the U.S. It leads you to traditional churches and other architectural and natural wonders, like the Bridge of Flowers or the Glacial Potholes in Shelburne Falls. The potholes are a bit more interesting than the Bridge of Flowers, but hey, I never was that close with flowers.

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This is, of course, just a small list of things to do in Massachusetts, and this New England state has so many things to discover. From a wide range of history, from the first settlers to the birth of American Liberty. Forests in the West, and beaches and seashores in the South. Massachusetts is worth visiting year-round, but each season has its unique personality. The change of colors of the leaves in fall, Christmas time in Boston, Halloween in Salem, and the beach year-round at Cape Cod. 

Have you been to Massachusetts? Have I forgotten anything to mention? Write to me below in the comment section. Do not forget to log in to Dream and Wanderland to receive all new posts about the Indian Summer first.

28 thoughts on “New England: 14 Unique Places And Things To Do In Massachusetts”

  1. I visited Massachusetts once, and it was quite some time ago- in 1997, to be exact. I visited many of the sites you mention here, like the Freedom Trail and Salem. But I didn’t make it to Cape Cod, Nantucket, Martha’s Vineyard, or other places. I need to make a return visit!

    1. Hi Bryan, thanks for stopping by and leaving a comment! You should try to go back and explore a bit more. Also, at Cape Cod, I found some nice places for a good pint of delicious beer! 😉 Definitely, worth another trip!

  2. There are certainly a lot of unique places to visit in this state! I’ve only heard of Boston and Salem, so I really enjoyed reading about the other points of interest you can visit.

  3. We recently returned from a trip to Boston and Salem and we absolutely loved the area. I am going to save your post so that we can go back and explore the other areas that you suggested!

  4. That was a really interesting list of places and the images that you shared are amazing! There’s so much to explore in Massachusetts and this list could be helpful as it’s very informative. Every traveler should visit Massachusetts at least once while planning a trip to US, it’s so beautiful!

  5. we are HUGE history buffs, so this is perfect for us! Thanks for all the tips, hints and suggestions. I’ve also wanted to visit the Berkshires too! Pinning for future reference

  6. Beautiful photos and great recommendations. We’ve done a New England road trip a couple of years ago, but misjudged the distances we had to cover and ended up cutting it a little short. Which unfortunately meant we didn’t make it to Cape Cod. So for sure need to go back and discover more

  7. The New England states are very popular with Irish people and always come recommended. Thanks to this post, I now see what everyone has been raving about. Lovely post.

  8. I haven’t been to Massachusetts yet, but I want to go. I’ve taught about Salem for years, and I’d love to see it for myself (I also want to watch the Boston Marathon one day in person!).

  9. We used to live in Boston, and I love so many of these spots! Somehow in living there for 4 years, I never made it to Nantucket OR Martha’s Vineyard though – hopefully on the next visit!

  10. Wow, there is so much to see in MA, I have only been to Boston and Cape Cod. Nantucket and Martha’s vineyard were already on my list and now you’ve inspired me to visit these other places too 🙂

  11. What an awesome list! I’ve only done a few of these but I definitely want to make the rest a bucket list! especially cape cod and Salem. Thanks for sharing!!

  12. Cape Ann and Cape Cod sound incredible! I’ll have to put it on my list when I decide to visit the US XX

  13. I’ve been to Massachusetts a few times and had a great time every visit. Martha’s Vineyard and Nantucket are very fond memories and I’ll always remember my very first Jimmy Buffett concert in Boston. Great post!

  14. Wow looks like a great tour of the NE .. I’ve nrvsr been – dying to go ! You have fueled my fire ha! Great pics 🙂

  15. This is such an informative post!
    I’ve never been to Massachusetts but I would love to include it in my east coast road trip whenever that happens. Anything involving Salem and Witches I’m down for! Great post!

    1. Thanks a lot, Victoria! I believe you will love Salem! I liked it, although I missed Halloween. I visited a few days too early… It is unbelievable how many awesome places are around which you never knew exists, isn´t it? 😀

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