11 Great Road Trips to Take in Massachusetts

Every once in a while, getting behind the wheel and hitting the open road helps the mind to unplug from the daily grind and freshen up. Luckily, the stunning New England countryside makes Massachusetts a prime destination for a road trip away from the urban hustle. With an array of hidden gems, a few hours outside big cities like Boston and Springfield, the Bay State offers travelers the chance to appreciate a picturesque landscape that seamlessly blends natural wonders, historic sites, and charming small-town allure.

From the rolling hills of the Berkshires to the rugged coastline of Cape Cod, Massachusetts presents a diverse tapestry of road trip possibilities, each promising an unforgettable adventure. Whether tracing the steps of the American Revolution, marveling at the serene beauty of glacial lakes, or discovering the quirky charms of cozy New England towns, these exciting road trips to take in Massachusetts are just what you need as a reprieve from the stresses of everyday life.

Boston To Cape Cod

This remarkable trip along the Massachusetts coast takes about an hour and a half, but countless detour opportunities allow you to take as much time as you need. With picturesque sights, cute little towns, and historical landmarks on the menu, you can brace for a satisfying experience. Early into the journey, stop in Duxbury for a tasty breakfast at French Memories to stock up for the journey ahead. Later, take a detour in Plymouth to discover intimate regional history. At Plymouth Rock, you can witness the site of the Mayflower Landing, where the historic ship brought the earliest European settlers to America.

Finally, as you draw to the end of your drive, take a break in the tiny village of Sagamore Beach to relax on the sandy shores of Scusset Beach State Reservation while soaking in the magical scenes of Cape Cod from afar.

Boston To The Berkshires

The drive to the Berkshires lasts just over two hours from Boston and introduces first-timers to the rich scenery of western Massachusetts. Meanwhile, several small towns conveniently dot the route, allowing for breaks to replenish, refuel, or discover unique local attractions. For instance, you might be interested in a photo opportunity in Grafton, beside the quirky Willard House and Clock Museum. This rustic cultural treasure sports stunning architecture dating back to 1718. Meanwhile, restock in Auburn with a hearty Chinese buffet at the family-friendly Yong Shing Restaurant.

If you are taking the trip in the cold season, consider a detour in West Becket to Canterbury Farm for snowshoeing and cross-country skiing fun. This lovely wilderness also houses different native wildlife for fantastic viewing opportunities.

Boston To Plymouth

Step back in time to discover captivating state history during this short trip to the historic village of Plymouth. The destination is about an hour from Boston and is perfect for those with limited time. A short drive from the starting point will bring you to the small town of Braintree, where you can shop for supplies at South Shore Plaza. Once you get to Hanover, use the opportunity to reconnect with nature in the serene atmosphere of Luddam's Ford Park. Its isolated setting is ideal for meditation while admiring the picturesque Indian Head River.

Eventually, Plymouth's wealth of historical markers provides a nostalgic journey into Massachusett's past. While there is so much to see and explore, remember to visit Plimoth Patuxet Museums and the National Monument to pay respect to the Forefathers.

Boston To Salem

Discover the curious history and spooky legends surrounding the rustic village of Salem, highlighted by the infamous witch trials. Luckily, Salem is under an hour's drive from Boston, making it one of the best road trips to take in Massachusetts if your time is constrained. Despite the brevity of the journey, you can stop in Stoneham for rare wildlife encounters at Stone Zoo. The 26-acre sanctuary harbors species like snow leopards and river otters. In Salem, there is no shortage of historical and cultural attractions. The House of the Seven Gables is an excellent place to start, preserving a 17th-century colonial mansion immortalized by Nathaniel Hawthorne's novel.

Also, the Salem Witch Museum and the Witch House are must-visits if you want to learn about the legendary witch trials. They host documents, archives, and memorabilia illuminating the landmark era.

Boston To Gloucester

A drive to Gloucester allows tourists to escape the chaos of downtown Boston for an easygoing time in a quaint fishing village. Stroll along sandy shores, visit historic sites, and sample fresh seafood. Notable attractions along the journey for discovery include the Samuel Parris Archeological Site in Danvers, which marked the genesis of the infamous Salem witch trials. Meanwhile, Gloucester invites travelers to slow down and revel in its soothing beach scenery. Good Harbor Beach is a prime destination, offering sugar-white sands for lazy strolls and gentle waves for surfing.

Once in town, you can't miss out on the savory seafood cuisine. There are numerous restaurants, but Seaport Grille stands out for its welcoming atmosphere and delicious flavors, from fried Ipswich clams to oysters.

Boston To Martha's Vineyard

Martha's Vineyard provides an ideal island getaway from Boston. The journey is around 3 hours, involving a mix of road driving and a ferry ride, resulting in diverse experiences. It offers several fabulous stops worth considering, and while on the road, you can stop in Woods Hole to browse the beautiful underwater creatures at Woods Hole Science Aquarium, home to over 80 marine species. A ride on the Steamship Authority Ferry will take you to Oak Bluffs, where you can soak up its coastal splendor at Joseph Sylvia State Beach.

Tisbury is another exciting location from which to explore Martha's Vineyard. It is home to the Martha's Vineyard Museum, whose exhibits detail the island's rich history from pre-colonial days to the present.

Boston To Nantucket

Nantucket provides road-trippers with another prime opportunity to depart the mainland and experience this quaint destination's island charm, whaling heritage, and vibrant arts. It is around a 4-hour journey but full of spectacular views and detours along the way. The road section of the trip ends in Hyannis, and this is a chance to explore local attractions like the John F. Kennedy Hyannis Museum. The lovely venue has interactive exhibits reflecting the late president's legacy and his family dynamics.

You can then take a ferry to Nantucket, where newcomers learn about its rich maritime heritage at the Nantucket Whaling Museum. The town also impresses with postcard-worthy lighthouses. If you carry a camera, be sure to capture the fascinating facade of Brant Point Lighthouse.

Boston To Springfield

If you want to change the scenery and explore another big city in Massachusetts, Springfield presents an ideal day trip destination from Boston, and vice-versa. This bustling location is chock full of attractions and sits one and a half hours away. However, the relatively short trip can be lengthened with various detours, including one at Framingham for a hike in Callahan State Park. If you enjoy craft breweries, consider stopping in Sturbridge for great-tasting local beers at Altruist Brewing Company.

While there is no shortage of places to visit upon arrival in Springfield, remember to check out the remarkable Naismith Basketball Hall of Fame. The venue is a great spot to learn about the history of basketball and its legendary players and coaches.

Boston To Concord

If you don't have enough time for a proper road trip, a half-hour drive to Concord from Boston easily fits into the itinerary. Nevertheless, you won't be deprived of experiences along the trip, especially for those with an affinity for historical attractions. Take a stop in Medford to discover its quaint historic district. The Hillside Avenue Historic District harbors well-preserved 19th-century structures. You will also come across the Alewife Brook Reservation in Cambridge, a lovely outdoor spot for communing with nature and watching beautiful bird species.

Cap off the journey with a tour of Concord's iconic landmarks, including the Minute Man National Historical Park and the North Bridge. These preserve intimate memories about the beginning of the American Revolutionary War.

Boston To Deerfield

Located around two hours west of Boston, Deerfield presents a quaint small-town escape that will take you on a riveting journey through time. But before that, the road winds past several delightful locations ripe for exploration. In Leominster, the Frances H. and Jonathan Drake House depicts life in the town during the Victorian era at the home of the famous abolitionist. About halfway through the drive, consider pausing in Westminster to eat something. The 1761 Old Mill is a terrific dining choice, serving savory American dishes in a rustic mill from the 18th century.

Finally, the excursion culminates in Historic Deerfield, a National Historic Landmark district preserving a three-century-old western Massachusetts village. The complex contains about a dozen structures and a museum chronicling the region's heritage.

Boston To Mount Greylock

Tourists who crave rigorous activity in the great outdoors won't mind hitting the open road for this three-hour voyage to Mount Greylock. You will be spoilt for choice of stops on the route to experience diverse local charms. As a warm-up to your eventual outdoor immersion, stop in Templeton to feel the green splendor of Otter River State Forest. Furthermore, make sure you are driving on a full stomach when you get to Millers Falls. You can pop into North Village Smokehouse and savor its pit-smoked barbecue.

If you still feel fresh when you get to Mount Greylock, grab your hiking gear and brace for a climb to the highest point in the state. Although challenging, the sweeping panoramas from the summit make the adventure worthwhile.

The diverse array of road trip destinations within Massachusetts presents travelers with the opportunity to discover the rare history, natural wonders, and small-town allure spread across the Bay State. Whether learning about the American Revolution in Concord, marveling at the serene beauty of Mount Greylock, or discovering the island idylls of Martha's Vineyard, these road trips through Massachusetts promise to deliver an unforgettable journey that showcases the state's remarkable diversity. From the rugged Berkshire peaks to the picturesque coastlines, the options for adventure-seekers and history buffs are truly boundless.