Massachusetts actually has several designated scenic byways meant to lead travelers through the most picturesque locations in the state. Criss-crossing most of western Mass., these gorgeous routes are filled with historical sites, beautiful “leaf-peeping” areas, quaint towns and villages, spectacular natural features, and some of the freshest air you’ll find anywhere. A drive along any one of these scenic byways will change the way you think of Massachusetts forever. Let’s take a look at these magnificent Massachusetts scenic byways.

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Have you driven along any of these fantastic Massachusetts scenic byways? Are you lucky enough to live off of one of them? Let us know in the comments. If you’re looking for more reasons to take a road trip, check out these country roads in Massachusetts.

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Road Trip Attractions in Massachusetts

What are some hidden gem attractions in Massachusetts?

Hidden gem attractions in Massachusetts include:

  • The Brattle Bookshop in Boston. This is one of the oldest antiquarian bookshops in the nation, which opened in 1825. 
  • Castle Hill at the Crane Estate in Ipswitch. Gorgeous gardens are combined with stunning ruins and ocean views to make this an unforgettable destination.
  • Stockbridge General Store in Stockbridge. Norman Rockwell used this as inspiration for several of his paintings and it is replete with New England charm.
  • Bancroft Tower Castle in Worcester. This castle was built in 1900 to memorialize George Bancroft who was born at this place in 1800.

Discover more about these and other hidden gem attractions in Massachusetts

What are the most beautiful places in Massachusetts?

The most beautiful places in Massachusetts include:

  • Boston Harbor Islands. These are all part of a national park and are wonderful for camping, swimming, and seeing wildlife.
  • Chatham Lighthouse Beach. The white sands, lovely seashore, and stunning lighthouse combine for views that are breathtaking.
  • Mohawk Trail. This was once a trade route used by Native Americans and it’s also one of the most scenic places in the state.
  • Stellwagen Bank National Marine Sanctuary. This is a place where you can see whales, dolphins, seals, and other marine wildlife.

Discover more about the most beautiful places in Massachusetts.  

What are the smallest towns in Massachusetts?

The smallest towns in Massachusetts include:

  • Tyringham. This tiny village’s name came from Norse roots which became Olde English and it means the Home of Tyr. 
  • Savoy. This was originally called New Seconk when it was settled in 1777 and it has a population of 692 people.
  • Middlefield. This town of 521 people got its start in 1783 and it is full of bucolic beauty and New England charm.
  • Gosnold. With only 75 people, this is certainly the tiniest town in the state and its town hall is literally a house. 

Find out more about the smallest towns in Massachusetts