There’s nothing like hopping in your car, rolling the windows down, and taking off for a long drive. It’s almost a right of passage, especially during the warmer months of the year. Massachusetts is filled with scenic roads and beautiful byways that make the journey just as special as the destination. Check out some of the best scenic drives in Massachusetts to take when you just can’t resist the call of the open road.

1. Mount Greylock Scenic Byway
Mount Greylock, Adams, MA 01220, USA
Flickr/Stevetheretired
This scenic road will take you through 16.3 miles of gorgeous countryside and lush forests. The foliage in the fall is particularly stunning along this route. It's the perfect road to take when you don't have any particular destination in mind but want to see something beautiful. If you stop at the summit of Mount Greylock and Western Gateway Heritage State Park, the drive will take you about two hours. Find out more about one of the best driving roads in Massachusetts on the Housatonic Heritage website.

Take a look at this video by @MileMarker4k:
2. Route 6A
Massachusetts 6A, MA-6A, Provincetown, MA, USA
Flickr/Doug Kerr
Route 6A is also known as Old King's Highway, as a portion of it served as the royal route during the early years of colonization on the Cape. Today, it's the beautiful, winding road that runs east to west across the arm of the Cape. Historic buildings line the route, and it's a great way to get a taste of the beauty of this region. It's one of the best drives in Massachusetts. Visit the Cape Cod Chamber website for more information.
3. Chickatawbut Road
Chickatawbut Road, Chickatawbut Rd, Quincy, MA, USA
Wikimedia Commons/Jameslwoodward
This scenic road is close to Boston so city dwellers should definitely check this one out. It runs from Braintree to Milton and passes through beautiful forest and past the craggy cliffs and slopes of the Blue Hills. Stop by the Blue Hills Reservation to get out and stretch your legs. Visit the Friends of the Blue Hills website to learn more.
4. Jacob's Ladder Scenic Byway (Route 20)
Jacob's Ladder Trail, US-20, Russell, MA 01071, USA
Flickr/Doug Kerr
The Jacob's Ladder Scenic Byway is a beautiful route through the foothills of the Berkshires. You can take this route through the center of the town of Lee and admire the gorgeous architecture of this sleepy and historic town. Head to Jacob's Ladder Scenic Byway website to learn more.
5. Central Hills Loop
New Salem, MA, USA
Flickr/Henry Zbyszynski
Taking the Central Hills Loop route through New Salem near the Quabbin Reservoir affords beautiful views of the water and green forests. Driving through the village of Gilbertsville in Hardwick, you’ll pass over a lovely covered bridge and have the opportunity to stop at Hamilton Orchards. It's one of the most beautiful Massachusetts scenic drives.

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6. Connecticut River Byway
01375, Sunderland, MA 01375, USA
pedrik/Flickr
This stunning road will take you through fertile farmland and miles of historic sites. There are actually 1,200 nationally recognized historic sites and buildings along the byway, so you won't be lacking in roadside entertainment. The Connecticut River Byway is also a charming road to take in the fall as the leaves are changing. Visit the Western Massachusetts Scenic Byways website for more information.
7. Cape Ann Shore
Cape Ann, Rockport, MA 01966, USA
Flickr/Ollie Jones
Driving along the rocky coast of Cape Ann guarantees loads of salty sea breezes and ocean views. If you start in Salem and end in Rockport you'll cover roughly 21 miles and pass plenty of things to do in between. Don't forget to stop at a roadside seafood shack! Head to the Cape Ann Chamber of Commerce website
8. Mohawk Trail Scenic Byway
Mohawk Trail, North Adams, MA, USA
Flickr/Massachusetts Office Of Travel & Tourism
This route was based on a Mohawk footpath and will show you some of the best scenery this state has to offer. Travel this road in the fall for an eyeful of vibrant foliage, or hop on in the spring or summer to check out places like Old Greenfield Village and the Barton Cove Recreation Area in Gill. The entire route covers about 42 miles and is one of the best scenic drives in Massachusetts. Visit the Mohawk Trail website for more information.

Take a look at this video by @MileMarker4k:
9. Southwest Berkshires
The Berkshires, United States
Flickr/Massachusetts Office Of Travel & Tourism
If you hop in your car and drive the 27 miles between Sheffield and Pittsfield, you'll encounter all sorts of beautiful sites. Stop by the Pittsfield State Forest for a dose of nature and then head to the Hancock Shaker Village for a trip back in time. Head to the Visit Massachusetts website to learn more about this scenic drive.
10. Lexington to Concord
Lexington, MA, USA
Flickr/Peter Lee
No two town names are so recognizable a pair as Concord and Lexington. These historic towns played a crucial role in the Revolutionary War, and driving the seven miles between them is a treat in all seasons. Stop by the Minute Man National Historic Park to learn about the famous conflict and spend the night at cozy Concord's Colonial Inn. For more information, visit the Battle Road Byway website.

What do you think about the best scenic drives in Massachusetts? Have you ever taken any of these drives? Share with us your experience in the comments section! Or, for more road trip inspiration, check out these places to visit in Massachusetts on your next weekend off.

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More to Explore

Best Scenic Drives In Massachusetts

Marisa Roman | June 21, 2021

What are the best road trips through Massachusetts?

Here are some of the best road trips through Massachusetts:

 

Check out this list of the best road trips in Massachusetts.

Where can I go on one tank of gas in Massachusetts?

Perhaps you enjoy winding down the beautiful backroads in Massachusetts but don’t want to spend an arm and a leg on gas. Don’t worry, we have you covered with these one-tank-of-gas places in Massachusetts. A tank of gas usually will take any car between 300 to 500 miles, so each stop on our list is around 275 miles in total. Adventure from New England Sports Park in Amesbury to The Castle Restaurant in Leicester, and more!

What are the best day trips in Massachusetts?

Some of the best day trips in Massachusetts include:

  • Kimball Farm in Westford
  • The Three Sisters Sanctuary in Goshen
  • Taza Chocolate Factory Tour in Somerville

 

There are so many incredible hidden attractions that make for the best day trips in Massachusetts. Depending on the season, you might want to rearrange your schedule a bit, as these fall day trips are pretty rewarding during autumn.

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