5 Historic & Beautiful Scenic Drives in Massachusetts

It’s difficult to pick our favorite thing about Massachusetts – there are just so many! Not only is Massachusetts a state rich with America’s history, but it’s also home to breathtaking landscapes, wind-blown seashores, and scenic mountain ranges. 

We want you to see the best that this small (but mighty) New England state has to offer, so we’ve gathered the five best scenic drives in Massachusetts that are perfect for your inner historian, hiker, colonial soldier, and anything in between. 

5 Scenic Drives in Massachusetts

1. Scenic Drives in Massachusetts: Mount Greylock Scenic Byway

• Distance: 17 miles
• Time needed: 2.5 hours to 1 day

Take in the breathtaking views of Massachusetts’ highest point at the conclusion of Mount Greylock Scenic Byway. This short route from Lanesborough to North Adams offers spectacular panoramic views, endless trails, and more. 

Begin your journey in Lanesborough, where you can squeeze in some retail therapy at the Berkshire Mall before heading into the great outdoors. 

You’ll soon enter Mount Greylock State Reservation, where you can explore over 70 miles of trails perfect for hiking, biking, and even a little bird watching. 

Make sure to budget enough time to climb to the top of the Veterans War Memorial Tower, a towering 92-foot structure that stands at the pinnacle of Mount Greylock. Experience some of the best views in Massachusetts from the top of the tower. They’re well worth the climb – we promise!

You’ll conclude your drive in artistic North Adams, where you can stroll through the Massachusetts Museum of Contemporary Art, visit Windsor Lake, or learn about local history at the Heritage State Park and Museum.

Pro Tip: If you plan on staying the night, we recommend the Blackinton-Manor Bed & Breakfast, a local favorite! 

When to go: You’ll need to take this scenic Massachusetts drive between May and October, as many roads are closed for the winter. 

2. Scenic Drives in Massachusetts: Essex Coastal Scenic Byway

• Distance: 85 miles
• Time needed: 4-5 hours or 1 to 2 days

Experience the best of what coastal New England has to offer when you travel along the Essex Coastal Scenic Byway. This Massachusetts scenic drive has everything – craggy shorelines, charming seaside villages, towering mansions, and more. 

We recommend taking at least a day to enjoy this scenic Massachusetts drive from Lynn to Salisbury fully. On your journey, you’ll pass through 14 communities, many of which host miles of sandy beaches, mouthwatering seafood restaurants, and miles of hiking and biking paths. 

Notable sites along the way include the town of Beverly, which is often called the birthplace of the American Industrial Revolution and the United States Navy. Or you can visit the Essex Shipbuilding Museum in Essex before spending an hour or two of antiquing in the oft-referred “America’s Antique Capital” before moving on. 

The Essex Coastal Scenic Byway also has plenty of family-friendly attractions along the way, like Salem Willows Arcade and Park in Salem. Young sea lovers will marvel at the exhibits in Real Pirates Salem, and there are also numerous trails and parks to burn off energy and enjoy time in nature – Old Town Hill and Hellcat Interpretive Trail, to name a few. 

When to go: You can travel the Essex Coastal Scenic Byway year-round, although some businesses and attractions may be closed during the winter season. Fall weekends can be exceptionally busy.

3. Scenic Drives in Massachusetts: Battle Road Scenic Byway

• Distance: 21 miles
• Time needed: 1 to 2 hours or 2 to 3 days

Fans of American history will love traveling along the Battle Road Scenic Byway, where the infamous ‘shot heard round the world’ spurred the beginnings of the American Revolution. The route takes you from Arlington to Concord, following the approximate path that the British used. 

You may need to take a day just to explore Arlington, also known as Menotomy, during the American Revolution. Paul Revere and William Dawes famously passed through Arlington, and it’s home to many fascinating cultural and historical sites like the Cyrus Dallin and George A. Smith museums, Jason Russell House, and Spy Pond Park, to name a few. 

The Minute Man National Historical Park also encompasses three areas along the Battle Road Scenic Byway: the towns of Concord, Lincoln, and Lexington. Visitors can walk the same battlegrounds as the Revolutionary soldiers and explore the many trails, historical structures, and notable sites on the grounds. 

We’d be remiss if we didn’t mention a few attractions in Concord, the conclusion of one of the best scenic drives in Massachusetts. 

Concord was the site of the first resistance battle of the American Revolutionary War and was home to transformative minds such as Henry David Thoreau, Ralph Waldo Emerson, Bronson and Louisa Alcott, and Nathaniel Hawthorne. It is truly a town worthy of exploration! 

Pro Tip: Get in touch with your inner Thoreau by visiting Walden Pond State Reservation, a 462-acre park complete with a replica of Thoreau’s home.

When to go: You can drive the Battle Road Scenic Byway all year, although it’s a beautiful scenic drive during the fall with all the vibrant foliage!

4. Scenic Drives in Massachusetts: Mohawk Trail Byway

• Distance: 65 miles
• Time needed: 3 to 4 hours or 1 to 2 days 

Travel back in time on one of the oldest routes in American history, the Mohawk Trail Byway. This 65-mile road takes you through ancient forests, historic towns and landmarks, and magnificent views. 

Before this Massachusetts scenic drive carried automobiles, it was a Mohawk Native American trading and hunting route. In fact, you can still hike a 34-mile stretch of Mohawk footpaths along the recreated Mahican-Mohawk Trail. 

Aside from its many natural attractions, the Mohawk Trail Byway also contains many cultural wonders. You can visit the Museum of Contemporary Art in the Hoosic River Valley or travel a few more miles to Williamstown. There, you can spend an hour (or two) at the Williams College Museum of Art and the Sterling and Francine Clark Art Institute. 

Recreational activities abound along this scenic drive in Massachusetts, where you can experience the breathtaking wonders of the Bridge of Flowers, see bald eagles’ nests in Barton Cove, and canoe down one of the byway’s five major rivers. 

When to go: The Mohawk Trail Byway is open year-round, with spectacular fall foliage photo opportunities and outdoor activities available in the warmer months. 

5. Scenic Drives in Massachusetts: Cape Ann Shore

• Distance: 21 miles
• Time needed: 1 to 2 hours or 1 day

The Cape Ann Shore coastline drive is a popular Boston day trip, offering plenty of breathtaking seaside views in the span of 21 miles. Beginning in Salem and ending in Rockport, you’ll have many opportunities to take in the sights along the way.

Begin your route in Salem, a town steeped in some of the darkest periods of America’s history (an extremely popular fall road trip for Halloween junkies!). You can easily spend a day exploring Salem, so take at least a few hours before beginning your drive.

Pro Tip: Try a burger from the Boston Burger Company. You won’t regret it!

There are many noteworthy stops along the Cape Ann Shore coastline, like Halibut Point State Park. Breathe in the salty sea air, stretch your legs, and explore the park’s wealth of trails and tide pools. Or spend an afternoon whale watching in Gloucester, where visitors can often spot humpback, blue, and even a few rare North Atlantic right whales. 

Finish your tour in Rockport, a quaint seaside village most famous for Motif #1, a fishing shack that is America’s most frequently painted building. Stroll down the winding streets while enjoying a lobster roll from The Lobster Pool before driving back home. 

When to go: The Cape Ann coastline drive is most enjoyable between late spring and early fall.