10 Best Road Trips to Take in Massachusetts
A laid-back road trip along Massachusetts' renowned highways offers travelers a unique opportunity to discover some of the country's most diverse and picturesque natural landscapes. From the sandy shores hugging Cape Cod in the east to the dense forests synonymous with the Berkshires in the west, it is a journey with a mixed bag of delightful surprises.
Between the start-off point and the destination, cute little towns, beautiful state parks, and roadside attractions present road-trippers with a glimpse of the state's historical heritage, cultural outlook, and natural splendor for a wholesome experience. Whether you are embarking on a solo trip or journeying with friends and family, these are some of the best road trips to take in Massachusetts.
Connecticut River Byway (39 miles / 63 km)
The scenic Connecticut River Byways stretches 39 miles (63 km) from north to south along the fertile course of the Connecticut River Valley. It is an exciting journey that exposes travelers to early American history as it passes through several historic villages dating back to Colonial times. Boasting several recognized historical sites and monuments along the route, there is no shortage of roadside entertainment to fuel your excitement. Some notable highlights to watch out for include the Connecticut River Greenway State Park, which offers 1,000 acres of hiking trails, waterfront vistas, and wildlife-watching opportunities.
The road also traverses the town of Deerfield, where the iconic Historic Deerfield Living History Museum profiles the colorful past of the Connecticut River Valley. In addition to the different sites, drivers can abandon their vehicles to exercise their legs while soaking up rich outdoor scenery.
Mohawk Trail Scenic Byway (69 miles / 111 km)
This beautiful roadway opened in 1914 and became a sought-after route for adventure lovers looking to discover the beauty of rural Massachusetts. The Mohawk Trail Scenic Byway stretches 69 beautiful miles (111 km) and links dramatic vistas, historic towns, and scenic hiking trails for an unforgettable escapade. The trip exposes bustling art communities showcasing rich local heritage. As it meanders through Williamstown, you can take a break to explore intricate creations inside the Williams College Museum of Art.
The journey also crisscrosses several rivers, allowing access to fun adventures like rafting and kayaking on the Deerfield and Millers Rivers. Meanwhile, hiking enthusiasts will gladly take on the Mahican-Mohawk Trail to test their mettle.
Mount Greylock Scenic Byway (16 miles / 26 km)
Discover the beauty of the Mount Greylock State Reservation along this 16-mile (26 km) climbing path in the Berkshire Mountains. The route's high altitude delivers stunning views of Massachusetts backcountry gems. It comes to its own in fall, with the changing foliage transforming the environment into a colorful natural wonder. Travelers following the parkway can access 70 miles (112 km) of nature trails that accommodate hikers, bikers, and bird-watchers, highlighted by a section of the Appalachian Trail.
The Bradley Farm Trail Loop is one of the most popular hikes for tourists looking to explore the thick wilderness surroundings. Dozens of vantage points encourage road-trippers to pause momentarily and take in the stunning scenery from above.
Historic Route 6A (62 miles / 100 km)
This scenic road along Cape Cod is also called the Old King's Highway. It cuts through a wealth of timeless historic sites, making it one of the best road trips to take in Massachusetts. The highway spans 62 miles (100 km) between Bourne and Orleans and traverses a combination of preserved farmland, salt marshes, and coastline. Driving along is a chance to witness centuries-old architectural styles in historic homes, restored inns, and ancient churches. Be sure to check the Old King's Highway Historic District of Barnstable, which houses over 500 ancient buildings and is listed on the National Register of Historic Places.
Other than history, alternative activities include walking on sandy beaches. Another exciting consideration is stopping by the beautiful Cape Cod Organic Farm to shop for fresh vegetables and organic meat.
Jacob's Ladder Scenic Byway (35 miles / 56 km)
This beautiful pathway is considered the ideal option for travelers visiting western Massachusetts. It sprawls approximately 35 miles (56 km) and crosses 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. Jacob's Ladder Scenic Byway delights with well-preserved historical living history and a taste of unique New England culture.
Cultural attractions worth checking out feature the popular Jacob's Pillow Dance Festival, scheduled for August in the historic community of Becket. Furthermore, consider pausing the journey in Lee to admire 19th-century architecture and spend quality time shopping cheaply at the Lee Center.
Essex Coastal Scenic Byway (90 miles / 145 km)
Explore historic seaports, ancient villages, and Colonial farms when traveling along this extensive roadway along Massachusetts North Shore. The Essex Coastal Scenic Byway stretches approximately 90 miles (145 km) and winds past several beautiful communities with exciting legacies, including Gloucester and Newburyport. Each stop has something to offer tourists traveling the byway. For instance, Ipswich harbors a delightful coastal atmosphere flanked by a collection of First Period dwellings providing a window to the 17th and 18th centuries. Meanwhile, Newburyport delights with its shipbuilding heritage and distinct Federal-era architecture.
Also, Essex has pleasant antique shops where you can hunt for vintage souvenirs. Those who appreciate Mother Nature's beauty can discover a thriving ecosystem across the Parker River National Wildlife Refuge.
Battle Road Scenic Byway (15 miles / 24 km)
This historic pathway follows the route used by the British regulars in the lead-up to the American Revolution. It extends approximately 15 miles (24 km), plying through the quiet towns of Lincoln, Lexington, and Concord. While the journey is relatively short, multiple points of interest along the way allow you to prolong the experience while making it fun and memorable. Exploring the route offers a fresh perspective on the American Revolution by exposing users to literary and technological implications associated with the landmark event.
Noteworthy highlights that add to the experience on the road include Lexington Battle Green, a landmark conflict location that altered colonists' relationship with the British government. The route also traverses a portion of the sprawling Minute Man National Historical Park.
Central Hills Loop (57 miles / 92 km)
This remarkable 57-mile (92 km) journey takes tourists through several beautiful towns in central Massachusetts, each with unique natural scenery and points of interest. Possible stops in your itinerary are New Salem, Ware, Hardwick, and Pelham. While the Central Hills Loop is accessible throughout the year, fall is the best season for this trip as the foliage changes color. Besides the alluring greenery, you can stop at different overlooks to catch glimpses of stunning rock formations.
As you start, pass by the New Salem Preserves & Heritage Cider and sample delicious apples from the region and well-prepared doughnuts to stock up for the journey ahead. Upon reaching Hardwick, you will want to pull over to the curb and enjoy the cozy atmosphere of its historic covered bridge.
Boston to Plymouth (40 miles / 64 km)
Boston makes for an idyllic jump-off base for visitors planning to explore the state on an exciting road trip. The journey from Beantown to Plymouth lasts about an hour and covers 40 miles (64 km), delivering a mix of historical and urban attractions as you move along. While you will not run out of points of interest worthy of a stopover, the Plimoth Patuxet Museums (otherwise known as the Mayflower Museum) is an enticing prospect, presenting an opportunity to familiarize yourself with historic immigrant crossings.
Once in Plymouth, consider going for a captivating whale-watching excursion off the Atlantic coast, with a chance for rare encounters with humpback and pilot whales. Alternatively, you can visit Stellwagen Bank Marine Sanctuary to admire its cute sea creatures.
Lexington to Concord (7 miles / 11 km)
This short trip between these two iconic Massachusetts towns is perfect for those who do not have much time to spend on the road. It takes about 15 minutes between Lexington and Concord, and road trip fans get a front-seat pass to the inner details of the American Revolutionary War when driving along the 7-mile (11 km) highway. The major highlight here is the Minute Man National Historical Park, which provides a glimpse into the landmark conflict and several factors that led to its occurrence.
The site hosts several battlefields and historic structures, allowing you to relive the famous dispute. Although there are not many attractions on the road, the trip's historical significance makes it a popular option when your time is limited. The route also passes along the Louisa May Alcott’s Orchard House and Concord Museum for endless exhibits into the past.
Final Thoughts
Whether you seek to experience scenic coastal views, historic small towns, or bustling urban attractions, the Bay State delivers memorable backroad adventures. From Cape Cod to the Berkshires, each region uncovered along these beautiful road trips to take in Massachusetts immerses travelers in the diverse charms this New England jewel offers. Explore beaches, forests, museums, charming ports, and more without missing the experiences that make Massachusetts a top destination. Planning a variety of loop trips for the year guarantees pleasant discoveries around every bend in the road.
