The 6 Best Scenic Byways to Fully Experience Massachusetts

Posted by
Sarah Lamagna
April 11, 2023
Updated January 16, 2024

scenic drives in massachusetts
Photo: PT Hamilton

Whether it’s mountain summits, historic towns, or coastal cliffs, Massachusetts does not disappoint, even from the windows of your car.

The Bay State might be known for its passionate (and sometimes unruly) sports fans, but there’s more to Massachusetts than just “Bah-ston”. There are over 150 state-owned parks and recreation areas, 18 National Park Service sites, and hundreds of quaint New England towns waiting for you to visit. So whether you’re a history buff, an outdoor recreation guru, a beach bum, or an art aficionado, these byways are made for you.

As always, make sure to check the status of the road closures. Some roads are only open seasonally due to snow or hazardous conditions. And keep in mind that New England is famous for its “leaf peeping” season during the fall, when a drive through the state will be at its most impressive.

1. Mount Greylock Scenic Byway

massachusetts scenic drives - mount greylock
Photo: Keith J. Finks

Why you should go: check out the highest point in Massachusetts without having to hike up the mountain.

  • Distance: 16 miles
  • Drive time without stops: 45 minutes

Most locals and visitors know of Mount Greylock. It’s the Bay State’s highest point and lies within Mount Greylock State Reservation. The scenic byway to get to the summit is a trip in and of itself. You can start the drive from the northern end of Lanesborough and drive north on Greylock Road, which turns into Rockwell Road until you reach the summit.

If you are visiting during the busy autumn months, expect to move at a snail’s pace (which will give you ample time to soak up the views). Sometimes, it might actually be faster to hike up Mount Greylock than drive it. Once you make it to the summit, you can get out and walk around the short trails that circle the Veterans War Memorial Tower and Bascom Lodge. You can eat breakfast, lunch, and dinner at the Lodge while you’re visiting. It’s also a stopover for many thru-hikers walking the Appalachian Trail.

Afterwards, get back in your car and keep heading north to the town of North Adams. This is a rural road so there are no gas stations or towns to shop in while en route. Traveling along this byway is more about immersing yourself in nature than going on a shopping spree. However, the town of North Adams has plenty of shops and restaurants for you to explore at the end of your journey.

More Information: Visit MA or Mount Greylock State Reservation

2. Jacob’s Ladder Trail


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Why you should go: it’s the quieter side of the Berkshires, but has so much culture.

  • Distance: 33 miles
  • Drive time without stops: 1 hour and 30 minutes

Route 20 traverses the southern end of the Berkshires in western Massachusetts and goes through several historic towns. Locals and visitors enjoy how the architecture here has remained unchanged, preserving its deep history. Once the major turnpike was built, folks stayed away from the more rural roads.

Although Jacob’s Ladder Trail isn’t used by truckers or long-distance travelers much anymore, it was once a busy interstate. The byway was first built in 1910 to accommodate the growing popularity of automobiles. People wanted to go farther and faster than they would on a horse, so Jacob’s Ladder Trail was created. It brought economic development to the area in the early part of the 20th century and now is preserved for anyone who might want to see it.

More Information: Jacob’s Ladder Scenic Byway

3. Essex Coastal Scenic Byway

massachusetts scenic drives - essex coastal
Photo: Paula Stephens

Why you should go: the historic architecture and countless seaside towns.

  • Distance: 90 miles
  • Drive time without stops: two hours and 30 minutes

As the longest scenic byway on this list, it also happens to be the most popular – especially during the summer months. The byway meanders through fourteen different communities, each with its own flare on seaside life.

It starts just north of Boston in a town called Lynn and heads north toward the New Hampshire border. One of the first major towns you’ll come across is Salem. The town, as expected, gets very crowded in October when Halloween is in full swing and is worth a visit to check out its witchy history. Then keep heading north where you’ll pass through more small towns until you reach the gorgeous village of Rockport. Stop by one of their many beaches, visit the Old Burial Ground, or check out one of the historic lighthouses.

Then, continue on to Newbury and Newburyport. Take a side trip over to Plum Island and the Parker River National Wildlife Refuge to see some of the largest concentrations of bird species in the state. Newburyport is packed with shops and restaurants for any fashionista or foodie. End your day in Salisbury where you can park yourself on their five-mile-long beach in town.

More Information: Essex Coastal Scenic Byway

4. Battle Road Scenic Byway

massachusetts scenic drives - battle road
Photo: Alexey Stiop

Why you should go: perfect for the history buff.

  • Distance: 14 miles
  • Drive time without stops: 30 minutes

You might not have heard of the Battle Road Scenic Byway, but it’s certain that you know of “the shot heard round the world”. It was the opening shot of the battles of Lexington and Concord, and the official start of the American Revolutionary War. Just like the battles, the road travels between Lexington and Concord with many historic monuments and stops along the way.

Route 2A runs along the towns of Arlington, Lexington, Lincoln, and Concord. You can visit Minute Man National Historic Park to learn all about the famous battles. If you happen to find your way there around mid-April, there is an annual reenactment of the battle put on by hundreds of volunteers.

More Information: Visit MA

Related Read: The 8 Most Magical Treehouses in Massachusetts

5. Old King’s Highway


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Why you should go: you’ll be surrounded by dozens of recreation opportunities.

  • Distance: 62 miles
  • Drive time without stops: 2 hours

Winding its way along the northern shore of Cape Cod is the Old King’s Highway. This historic road passes through quaint towns like Barnstable, Yarmouth, and Sandwich, all the way to Provincetown. It’s also much less busy than Route 28, which runs along the southern border of Cape Cod. But if you’re visiting the area in the summertime, expect long delays and lots of traffic.

While you’re going at a snail’s pace, you might as well stop and check out the plethora of activities to partake in and things to see. The Heritage Museum and Gardens in Sandwich as well as the Historic Village are both worth a break to stretch your legs. Make sure to stop by the Glass Museum and grab tea or brunch at Dunbar House while you’re there.

Then continue on through Barnstable where you can tour the Coast Guard Heritage Museum. Or stop in Yarmouth at the Winslow Crocker House. One of the most unique stops along the way is the Jonathan Young Windmill. End your journey in Provincetown where you can partake in all the fun and flare the town is known for.

More Information: Route 6A and Cape Cod Chamber of Commerce

6. Mohawk Trail Byway

massachusetts scenic drives - mohawk trail
Photo: Belia Koziak

Why you should go: to learn more about the indigenous cultures in the northeast.

  • Distance: 69 miles
  • Drive time without stops: 2 hours

This route dates back more than 10,000 years, when indigenous communities used the path as a trade route. Nowadays, most visitors along this route start their journey on the eastern side, in Athol. There’s a wonderful environmental park as well as a Bird and Nature Club with lots of events throughout the year.

The next stop is in Orange, where you can shop for antiques. You’ll then pass through Erving, Farley, and Millers Falls. When you get to the Connecticut River, you’ll be crossing over the French King Bridge which is one of the best places to view the fall foliage. When you get to Riverside, if you cross the bridge to Turners Falls, check out Great Falls Discovery Center and the Fishway along the river.

Keep heading west until you reach Shelburne Falls where you can view the Bridge of Flowers (seasonal). It’s exactly what you think it is and one of the most beautiful things you’ll ever witness. After you’ve had your fill of flowers, keep going west to see the Hail to the Sunrise monument in Charlemont which gives homage to the Mohawk people.

Finally, you’ll reach the famous hairpin turn just east of North Adams (you’ll know it when you drive it). Make sure to time your visit to North Adams accordingly to see everything it has to offer. It’s a huge mecca for artists across New England and even houses the Massachusetts Museum of Contemporary Art.

More Information: Western Massachusetts Scenic Byways

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