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11 Best Road Trips + Itinerary

by Staff

When most people imagine New England, they think of sandy beaches, seafood, fishing boats, and long roads to nowhere. Lighthouses and rocky coasts are certainly a part of the image, too. But, undoubtedly, of all the states in the region, there’s only one that offers every element of the quintessential New England. Massachusetts has it all! From winding roads to wide open beaches, hiking trails to roadside wonders. If you’re interested in seeing all of this, it might be time to consider a journey through the state. Here are a few of the best road trips in Massachusetts to get you started. Each one is fun, but all offer something uniquely different. Check them out the next time you’re adventure-ready!

As you decide which road trip to take first, check out OnlyInYourState’s Ultimate Road Trip Packing List for our best road trip planning and packing tips. Whether you’re leaving for a single day or a week-long road trip, you can’t forget the snacks: here are 50 on-the-go snack ideas perfect for traveling.

1-Day Road Trip In Massachusetts

3-Day Weekend Road Trip In Massachusetts

The Coastal Massachusetts Road Trip

The Massachusetts Central Hills Road Trip

Best Massachusetts Road Trip For Spring

Best Summer Road Trip In Massachusetts

Best Massachusetts Road Trip For Fall

Best Winter Road Trip In Massachusetts

Family Friendly Massachusetts Road Trip

Road Trip to Massachusetts Landmarks & Natural Wonders

Road Trip to Best Small Towns in Massachusetts

Whether you make the journey from as close as Maine and New Hampshire or as far as New York or Canada, every mile spent on these road trips will be worth the gas. They showcase a different magnificent part of the state and are perfect for those who want to spend every day soaking up the beauty of the world around them. Have you been to any of the stops on these road trips? If you have any other Massachusetts road trip ideas, we’d love to read about them in the comments!

After tackling some of the best Massachusetts road trips on this list, consider heading out for more. Sometimes a road trip doesn’t even need any particular destination. If you appreciate the beauty of a trip almost as much as the destination itself, check out The King’s Highway, America’s oldest road, which travels right through Massachusetts.


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More to Explore

Things To Do In Massachusetts

Michelle S.
May 11, 2023

What are the most popular landmarks to visit in Massachusetts?

The most popular landmarks in Massachusetts offer lots of history and beauty. They can be found throughout the state. A few to visit first include:

  • The Mayflower Replica, Plymouth: While the original is long gone, this version is thought to be similar to the original ship that arrived in Plymouth Harbor.
  • The town of Sandwich: There are so many beautiful landmarks in this Cape Cod town that it’s worth planning a day trip to see them all.
  • The Endicott Pear Tree, Danvers: Considered the oldest fruit tree in the country, this unexpected landmark is actually fun to see.
  • The Old Stone Church, West Boylston: One of the most beautiful and scenic spots in the state, this church dates back to the 1890s. It was built as a replacement for a Baptist church that was destroyed in a fire.

What are the most popular state parks to visit in Massachusetts?

The most popular state parks to visit in Massachusetts include:

What are the major highways in Massachusetts?

The major highways in Massachusetts are:

  • I-84
  • I-86
  • I-89
  • I-90
  • I-91
  • I-93
  • I-495
  • Route 3
  • Route 3A

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