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Massachusetts Travel Guide: What NOT to Do

Posted on July 23, 2022July 11, 2022 by Mark Wolters

Hey there, fellow travelers! Today, we’re talking about what NOT to do when you visit Massachusetts. While many travel blogs will tell you the best things to see in Massachusetts, we want to be sure you know about the things you should NOT do as you tour the best places to visit in Massachusetts. See why they call it the “State of Wonder.”

It really is that gorgeous on the coast, but even better inland!

Don’t Think Massachusetts is Just Boston

Yes, Boston is the capital of Massachusetts, and largest city in the state, and a really fun city, but there’s more to Massachusetts than the city of Boston. Besides Boston, there are tons of cool places to visit in Massachusetts, like Cape Cod, Martha’s Vineyard, or the Berkshires. Don’t miss Boston, but make sure you check out other parts of the state, too.

Five Things You’ll Love & Hate about Boston

Don’t Say Things Wrong

From the pronunciations to the words used, sometimes you might think you’re hearing a whole different language in Massachusetts. Worcester is probably the most well-known mispronounced word. (It’s only two syllables, like Wooster.) But it’s also the way you say things. Instead of going to Cape Cod, you’re going to “the Cape.” You don’t go to Martha’s Vineyard, you go to “the Vineyard.”

Don’t Forget to Brush Up on History

There are so many cool historic sites in Massachusetts; it’s really the birthplace of the United States in many ways. It definitely helps you appreciate everything a bit more if you’ve recently brushed up on US history. Boston has the Freedom Trail which is really cool, and it’s lined with important cemeteries, churches, and other buildings. It’s like walking through history. You can also visit Plymouth, where Plymouth Rock is, as well as Salem, where the witch trials were held. Other notable Massachusetts residents include Susan B Anthony and Johhny Appleseed. There are historical markers all over the state!

Don’t Forget to Book Accommodation Early

If you plan to visit Massachusetts in the summer, get your accommodation early! Spring and fall weekends book up pretty far in advance, too. So don’t wait to pick your hotels or you may not have much to choose from.

Don’t Expect a Lot of Chains Outside of Boston

When looking for hotels in Massachusetts, don’t be surprised if you’re not finding a lot of Marriott or Hilton-type hotels. Outside of Boston, Massachusetts is more about small towns and locally-owned businesses. You may have to dig a little to find hotels, but Google Maps is great for zooming in to see what’s around. Likewise, aside from Dunkin Donuts, don’t bother with chain restaurants. Find out where the locals eat.

Eat until your heart’s content!

Don’t Pass Up a Parking Spot

If you visit Massachusetts in summer, do not pass up a parking spot! Whether you’re in Boston or some of the quaint coastal towns, don’t wait for the “perfect parking spot” because you may not find another one. Remember, Massachusetts was a state before cars came along, so it’s not exactly designed to handle a lot of cars.

Don’t Let the Massholes Get to You

Speaking of driving in Massachusetts, it won’t take long to see why other people call the residents “Massholes.” The drivers in Massachusetts are aggressive. Off the road, Massachusetts locals are as friendly as can be, so don’t take it personally if they cut you off or flip you off on the road! Just don’t expect to hear the accent you see in the movies; it’s not as common as you might think.

Don’t Let the “New England Shield” Fool You

The New England Shield is a trait common in parts of Massachusetts. The people tend to put up a shield and it can be offputting at first, but once you break that shield, New England locals are some of the most helpful people you will meet. They may not be the warmest people or the friendliest, but they will help you and give you recommendations.

Don’t Diss New England Sports

New Englanders are passionate about their sports teams, so don’t diss the Patriots, Celtics, Bruins, or especially the Red Sox in Massachusetts. If you decide to wear a Yankees hat in Massachusetts, prepare to be heckled.

Don’t Call a Frappe a Milkshake

For all intents and purposes, a frappe is what most of us would call a milkshake. But in Massachusetts, it’s called a frappe. It’s made with ice cream, milk, and chocolate syrup. So, if you want a milkshake, you have to order a frappe. If you order a milkshake in Massachusetts,  you’re going to get milk with syrup, basically flavored milk. The roadside stands have the best frappes (and clam strips, too!)

Simply Jocelyn shares what to eat in Massachusetts!

Don’t Expect to Find Liquor at the Grocery Store

You can buy beer at the grocery store in Massachusetts, but if you want anything stronger, you’ll have to go do the package liquor store, or “the packy.” It’s not a big deal, but you just have to plan ahead and know you’ll be making two stops when stocking up your vacation kitchen.

Don’t Come to Massachusetts in Winter

Winter in Massachusetts can be brutal. It’s very cold and they can get a ton of snow and ice. All the other seasons are spectacular, but winter is not the best time to visit Massachusetts. If you have to visit in winter, bring a heavy coat and good waterproof boots.

Don’t Miss the Berkshires!

The Berkshires are a region in Western Massachusetts known for small mountain towns and summer festivals. It’s a popular vacation destination in New England, especially for city dwellers of Boston. If you visit Massachusetts, Boston is a must, but you should also make time to visit the Berkshires. Just keep these “don’ts” in mind when you do:

  • Don’t forget to book accommodation early! We booked three months out and most accommodations were already booked for the best towns in the Berkshires.
  • Don’t forget about the “1 o’clock crunch” when it gets really busy with traffic. Everyone seems to head to lunch at the same time, so either eat early or make sure you have a lunch reservation.
  • Don’t expect continuous cell service. Our service was spotty when we left the main towns, so it’s never a bad idea to have a paper map in addition to your phone’s GPS.
  • Don’t let the traffic get to you. Weekend traffic gets pretty heavy, so just expect it and be patient. Allow plenty of time to get where you need to go.
  • Don’t think the Norman Rockwell Museum is his original studio. It’s a great place to visit, but his original studio was moved from town out to its current location.
  • Don’t miss the local museums. The Berkshire Art Museum is great and there’s also the Berkshire Museum in Pittsfield.
  • Don’t miss the fall colors! While most people think of Maine when they think of New England leaf-peeping, the Berkshires are really gorgeous in the fall as well.
  • Don’t forget to explore nature! While the best towns in the Berkshires are fun to visit, there are also a lot of outdoor things to do as well. Enjoy hiking, mountain biking, and even whitewater rafting!

Grab Some Wolters World Travel Gear!

Don’t be surprised if you fall in love with Massachusetts! Boston is such a great city and then there’s a whole state of cool attractions outside of Boston. From the coastal villages to the mountain towns, we love visiting Massachusetts. It’s the perfect destination for a summer or fall road trip! Want more New England travel tips? Check out some of our other blog posts:

  • Five Things You’ll Love & Hate About New England
  • What NOT to Do in New England
  • What to Eat in New England
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