Massachusetts Travel Guide
Historic New England and Lovely Landscapes…
Massachusetts is one of the oldest settled colonies in the United States is steeped with Revolutionary War history and colonial heritage.
Boston, the state’s capital, brims with Revolutionary War sites like the Freedom Trail and Faneuil Hall, alongside modern cultural attractions and a fantastic food scene.
You also have historic Salem, known for its dark past with the witch trials of the 17th century. In recent years, this has become a haven for Halloween season travelers.
Coastal towns such as Cape Cod and Martha’s Vineyard offer sandy beaches, gorgeous harbors, and luxury getaways.
In western Massachusetts, the Berkshire Mountains invite outdoor enthusiasts with hiking trails, an incredible arts and culture scene with festivals in the summer months attracting some of the nation’s best talent, a haven for creatives for centuries, and the historic charm of towns like Lenox and Stockbridge. This has quickly become one of our favorite escapes from New York City.
Fall transforms the state with fiery foliage colors, drawing visitors to witness nature’s spectacle in places like the Mohawk Trail and Mount Greylock.
From historic landmarks to the natural beauty, Massachusetts offers year-round options for traveling and enjoying the best of what this state has to offer.
Quick Tips for Visiting Massachusetts
When is the best time to visit Massachusetts?
The best time to visit Massachusetts is during the late spring (May to June) and fall (September to October).
During these seasons, the weather is typically mild and pleasant. Spring offers fewer crowds compared to the peak summer months.
Fall attracts New England leaf peepers and Salem is most visited during September and October for the fall season and Halloween traveler.
Late spring brings blooming flowers and moderate temperatures throughout the state.
Summer (July to August) brings warm weather perfect for beach outings on Cape Cod or Martha’s Vineyard, although popular destinations can be busy.
Winter (December to February) brings cold temperatures and occasional snow, ideal for skiing and winter sports enthusiasts in areas like the Berkshires and central Massachusetts.
How Much Time Do I need in Massachusetts?
To explore Massachusetts thoroughly, given its smaller size compared to other states, you can enjoy the main attractions in cities like Boston or historic towns like Salem and Plymouth in a long weekend of 3 to 4 days.
However, to fully experience the state’s beauty, plan to spend at least 5-7 days.
This timeframe allows you to visit more than one area combining areas like the Berkshires to your trip.
For places like Cape Cod you need a minimum of 3-5 days and for Martha’s Vineyard a minimum of 3 days.
What is Massachusetts most famous for?
Massachusetts is best known for its rich history dating back to the Pilgrims’ landing at Plymouth Rock and the American Revolution, which unfolded in cities like Boston.
In Boston, you’ll find renowned institutions of higher education such as Harvard University and the Massachusetts Institute of Technology (MIT).
The state also is full of colonial towns, offering visitors a glimpse into American heritage.
Massachusetts’ cultural scene thrives with world-class museums such as the Museum of Fine Arts, Mass MOCA, and the Isabella Stewart Gardner Museum.
Cape Cod and the Islands draw travelers with their pristine beaches and picturesque lighthouses, while the Berkshires showcase scenic landscapes and cultural retreats like Tanglewood.
The state’s culinary offerings range from fresh caught seafood along the coast to iconic dishes like Boston cream pie and clam chowder.
Any Must Try Food in Massachusetts?
The top must-try foods and regional specialties in Massachusetts are seafood-focused.
New England clam chowder is definitely a must-try, this creamy soup loaded with tender clams, potatoes, and a hint of smoky bacon.
Massachusetts is famous for its fresh lobster, best enjoyed in classic lobster rolls where sweet lobster meat is lightly dressed in mayo and nestled in a buttery, toasted bun. Although, we both prefer the version with just hot butter and lemon!
The state also has oyster farms dotted along the coastline from Cape Cod, Martha’s Vineyard, and the South Shore.
Boston baked beans, slow-cooked with molasses and pork, are a hearty dish steeped in history.
In the fall, try seasonal specialties like apple cider donuts, a seasonal treat bursting with warm spices and tangy apple flavor.
For dessert, try Boston cream pie, a rich cake layered with pastry cream and topped with chocolate ganache, a beloved local delicacy.
What’s the best way to get around Massachusetts?
The best way to get around Massachusetts as a traveler is primarily by car. This allows you the flexibility to visit different destinations across the state at your own pace.
Massachusetts also has scenic drives like the Mohawk Trail through the Berkshire Mountains and the coastal route along Cape Cod all offer breathtaking views and access to charming towns and natural attractions.
If you’re just visiting Boston (or even Salem in addition to Boston), you don’t necessarily need a car as public transportation is available and many areas are walkable. The Greater Boston transportation network of buses and subways are known locally as the “T”. There are also commuter rail services, including a great train route from New York City to Boston.
This makes it convenient to navigate within the city and its surrounding suburbs without the hassle of driving and parking.
Additionally, ferries provide a unique way to experience Massachusetts, especially for visiting islands like Martha’s Vineyard and Nantucket, known for their beautiful beaches and quaint seaside villages.
Renting a car remains the best choice for exploring more rural and scenic areas beyond the city limits.
Explore our guides
Boston
Boston is truly a special destination in the United States, not only is this a haven for history buffs, Boston is truly one of the most beautiful cities in the country with its cobbled lanes, and stunning architecture from colonial to modern designs.
The harbor is beautiful, the food is great, and historic sites are a plenty! We also love the ‘Emerald Necklace’ of parks the city has to offer. Or hopping over to Cambridge and walking through the beautiful Harvard University campus and surrounding area.
One area not to miss is the North End of Boston, aka Little Italy. There are plenty of great restaurants in the North End that may have you coming back to this area again and again, like we did!
The best part, most of Boston is accessible by foot! So wear comfortable walking shoes and get ready to enjoy one of the most history rich pockets of the United States.
Berkshires
The beauty of the Berkshires is truly incredible. Located in western Massachusetts, this area is renowned for its arts and culture scene from galleries to museums and their summer series of festivals that bring the best of the best in theater and performing arts at places like Tanglewood and Williamson Theater Festival.
The towns in this region are charming AF. I don’t say that lightly either. Artists like Norman Rockwell, and creatives like Herman Melville and Edith Wharton all were inspired by the region enough to have homes here.
Outdoor enthusiasts will love the mountains, a 90-mile section of the Appalachian Trail cuts through the Berkshires.
If you’re wondering where to base yourself while exploring the region, consider staying in mid-county in Pittsfield for a first-time visitor so you have easy access to the entire region.
Salem
One of the coolest colonial towns in the United States and best Halloween getaways is Salem! This historic seaside community has a dark past during the 1692 Witch Trials, but in recent decades this town’s tourism has embraced its popularity around the fall season and embraced its identity as a Halloween cultural hot spot.
Famous Halloween movies like Hocus Pocus have filmed around the city and in addition to the kitschy witch-themed attractions, there are plenty of historic sites and places to commemorate the wrongly accused in the 17th century in addition to some of the oldest buildings and homes in the country, like The Pickering House that dates back to 1664.
While visiting in the fall is the most famous time to visit (and most crowded) you can enjoy all the same activities and historic sites any time of the year.
