A relaxing road trip along Massachusetts’ famous highways offers travelers a unique opportunity to discover some of the country’s most diverse and picturesque natural landscapes. From the sandy beaches around Cape Cod in the east to the dense forests that characterize the Berkshires in the west, it’s a journey full of delightful surprises.
Between the starting point and the destination, quaint little towns, beautiful state parks and roadside attractions offer road trippers a glimpse of the state’s historical heritage, cultural vistas and natural splendor, making for a holistic experience. Whether you’re traveling alone or with friends and family, these are some of the best road trips in Massachusetts.
Connecticut River Byway (39 miles / 63 km)
The scenic Connecticut River Byways stretch 39 miles from north to south along the fertile Connecticut River Valley. It’s an exciting journey that introduces travelers to early American history as it passes through several historic colonial-era villages. With several recognized historic sites and monuments along the route, there’s no shortage of roadside entertainment to add to your excitement. Some notable highlights to check out include the Connecticut River Greenway State Park, which offers 1,000 acres of hiking trails, waterfront views, and wildlife-watching opportunities.
The road also passes through the town of Deerfield, where the iconic Historic Deerfield Living History Museum showcases the colorful past of the Connecticut River Valley. In addition to the various attractions, drivers can leave their vehicles behind to stretch their legs while enjoying the rich outdoor scenery.
Mohawk Trail Scenic Byway (69 miles / 111 km)
This beautiful road opened in 1914 and became a popular route for adventure seekers looking to discover the beauty of rural Massachusetts. Stretching for 69 beautiful miles (111 km), the Mohawk Trail Scenic Byway connects dramatic vistas, historic towns and scenic hiking trails for an unforgettable experience. The journey passes bustling art communities that showcase the rich local heritage. As you drive through Williamstown, you can pause to explore the intricate creations at the Williams College Museum of Art.
The trip also crosses several rivers, offering the opportunity for exciting adventures such as rafting and kayaking on the Deerfield and Millers Rivers. Hiking enthusiasts, meanwhile, can venture out onto the Mahican-Mohawk Trail to test their skills.
Mount Greylock Scenic Byway (16 miles / 26 km)
Discover the beauty of Mount Greylock State Reservation on this 16-mile climbing trail in the Berkshire Mountains. The route’s high elevation offers breathtaking views of the gems of Massachusetts’ backcountry, and it’s especially striking in the fall when changing foliage transforms the surrounding area into a colorful natural wonder. Travelers following the parkway can access 70 miles of nature trails that cater to hikers, cyclists, and birdwatchers, including a section of the Appalachian Trail.
The Bradley Farm Trail Loop is one of the most popular hikes for tourists looking to explore the area’s dense wilderness. Dozens of overlooks invite road trippers to pause and enjoy the stunning scenery from above.
Historic Route 6A (62 miles / 100 km)
Also called the Old King’s Highway, this scenic drive along Cape Cod passes through a variety of timeless historic sites, making it one of the best road trips in Massachusetts. The highway stretches for 60 miles between Bourne and Orleans, traversing a combination of preserved farmland, salt marshes, and coastline. As you drive, you can experience centuries-old architectural styles in historic homes, restored inns, and old churches. Be sure to visit Barnstable’s Old King’s Highway Historic District, which is home to over 500 old buildings and is listed on the National Register of Historic Places.
Alternative activities besides history include strolls on sandy beaches. Another exciting consideration is a visit to the beautiful Cape Cod Organic Farm to shop for fresh vegetables and organic meat.
Jacob’s Ladder Scenic Byway (35 miles / 56 km)
Considered an ideal option for travelers visiting Western Massachusetts, this beautiful trail stretches for approximately 35 miles and passes through several towns along the foothills of the Berkshire Mountains. These include Lee, Becket, Huntington, Chester and Russel, which serve as worthwhile stops with interesting local attractions during your trip. The Jacob’s Ladder Scenic Byway delights with well-preserved living history and a touch of unique New England culture.
Cultural attractions worth visiting include the popular Jacob’s Pillow Dance Festival, held in August in the historic community of Becket. Additionally, you can stop your trip in Lee to admire 19th-century architecture and do some inexpensive shopping at the Lee Center.
Essex Coastal Scenic Byway (90 miles / 145 km)
Discover historic seaports, old villages and colonial farms as you travel this long road along the northern coast of Massachusetts. The Essex Coastal Scenic Byway is about 90 miles long and winds past several beautiful communities with exciting heritage, including Gloucester and Newburyport. Each stop has something to offer tourists traveling the byway. For example, Ipswich offers a charming coastal atmosphere flanked by a collection of first-period homes that offer a glimpse into the 17th and 18th centuries. Newburyport, on the other hand, delights with its shipbuilding heritage and distinctive Federal Reserve-era architecture.
Essex also has lovely antique shops where you can browse for vintage souvenirs. Those who appreciate the beauty of Mother Nature can discover a thriving ecosystem at the Parker River National Wildlife Refuge.
Battle Road Scenic Byway (15 miles / 24 km)
This historic trail follows the route used by British soldiers in the lead-up to the American Revolution. It is approximately 15 miles long and passes through the quiet towns of Lincoln, Lexington, and Concord. Although the journey is relatively short, numerous points of interest along the way allow you to extend the experience while making it fun and memorable. Exploring the trail offers a new perspective on the American Revolution by introducing users to the literary and technological implications of this groundbreaking event.
Notable highlights that enhance the experience on the road include Lexington Battle Green, a significant site of conflict that changed the colonists’ relationship with the British government. The route also traverses part of the sprawling Minute Man National Historical Park.
Central Hills Loop (57 miles / 92 km)
This remarkable 57-mile journey takes tourists through several beautiful towns in Central Massachusetts, each with unique natural scenery and attractions. Possible stops on your itinerary include New Salem, Ware, Hardwick, and Pelham. While the Central Hills Loop is accessible year-round, fall is the best time of year to take this trip as the foliage changes color. In addition to the enticing greenery, you can stop at various overlooks to catch a glimpse of stunning rock formations.
As you begin, stop by New Salem Preserves & Heritage Cider for delicious local apples and well-made doughnuts to fuel you for the journey ahead. When you reach Hardwick, you’ll want to pull over to the curb and enjoy the cozy atmosphere of the historic covered bridge.
Boston to Plymouth (40 miles / 64 km)
Boston is an idyllic base for visitors looking to explore the state on an exciting road trip. The drive from Beantown to Plymouth takes about an hour and covers 40 miles, offering a mix of historic and urban attractions. While you won’t pass any interesting places worth stopping, the Plimoth Patuxet Museum (also known as the Mayflower Museum) is a tantalizing prospect and offers a chance to learn about the historic immigrant crossings.
When you’re in Plymouth, you can join a fascinating whale watching tour off the Atlantic coast, where you’ll have the chance to see humpback and pilot whales, or you can visit the Stellwagen Bank Marine Sanctuary and admire the cute marine animals there.
Lexington to Concord (7 miles / 11 km)
This short trip between these two iconic Massachusetts cities is perfect for those who can’t spend much time on the road. The drive from Lexington to Concord takes about 15 minutes, and road trip fans will get a glimpse into the inner workings of the American Revolutionary War as they travel the seven-mile highway. The biggest highlight here is Minute Man National Historical Park, which offers a glimpse into the historic conflict and several factors that led to its occurrence.
The site is home to several battlefields and historic buildings, allowing you to relive the famous conflict. Although there aren’t many sights along the road, the historical significance of the journey makes it a popular option if your time is limited. The route also passes Louisa May Alcott’s Orchard House and the Concord Museum, where you’ll find endless exhibitions into the past.
Final thoughts
Whether you want to experience scenic coastal views, historic small towns or bustling urban attractions, the Bay State offers unforgettable backroad adventures. From Cape Cod to the Berkshires, each region explored on these beautiful Massachusetts road trips immerses travelers in the diverse charms of this New England gem. Explore beaches, forests, museums, charming harbors and more without missing out on the experiences that make Massachusetts a top destination. When you plan a variety of road trips for the year, pleasant discoveries are guaranteed around every bend in the road.
