One of the original thirteen states, Massachusetts has a lot of history to explore and that certain kind of charm only found in New England. Discover this intriguing and varied state on a Massachusetts holiday, and uncover it’s beautiful bays, stunning beaches, flowing rivers and majestic mountains.
Holidays to Massachusetts are graced with picturesque towns and rolling hills. Autumn in Massachusetts sees a blanket of gorgeous autumn foliage; journey across the Berkshire Hills to see the state’s small towns get lost beneath warm tones of red, yellow and orange. Visit Rocky Mountain Park in Greenfield and hike up to Poet’s Seat Tower to take in breathtaking views of Greenfield, Connecticut Valley and Montague, or scale Mount Greylock and gaze over the 90 miles of undulating countryside. For a change of pace, head to Boston and take to the Freedom Trail, learning about the events that sparked the American Revolution as you go.
Discover Massachusetts’ Beautiful Islands
Just a ferry ride away from the Cape Cod peninsula sits the two adored summer holidays islands of Nantucket and Martha’s Vineyard. Take a tour of the iconic lighthouse at Gay Head on Martha’s Vineyard, then head to the town of Oak Bluffs and wander around the whimsical gingerbread cottages of The Campground. On Nantucket, take a trip to the Whaling Museum and learn about the island’s past as the whaling capital of the world. Explore the rest of the island by car or bike, luxuriate on the beautiful dune lined beaches and simply soak up island life.
Discover this beautiful area of the United States on a Best of New England tour; explore Boston, before journey across the varied terrain of Maine, taking in quaint lighthouses and sampling delicious seafood. Traverse Vermont’s White and Green Mountains and then head to the unspoilt beaches of Cape Cod to do a spot of whale watching. If you want to go further afield, take a flight to explore other states, or journey to the white sand beaches of the Caribbean.
Great sample itineraries
There’s so much to discover on a Massachusetts holiday, so why not take a look at our sample itineraries for some inspiration? Give us a call and let us plan your perfect trip to Massachusetts, tailor made for you.
New England Self Drive Holidays
Fall Leaves Tour New England
You'll never be lost for things to do in Massachusetts, from exploring the coastal towns and villages, to heading inland to the Berkshires or spending a few days in Boston. This is the prefect year round holiday destination whether you are heading to the beach in the summer along the charming Cape Cod peninsula, or heading to the hills in search of the blaze of the autumn colours. All you have to decide is when to come and discover all that Massachusetts has to offer.
Its safe to say that there is no where quite like Salem, Massachusetts. Discover the incredible history of the infamous Salem Witch Trials of 1692 that still makes the town so famous today. Take a walking tour of the Salem Heritage Trail or visit the Salem Witch Museum to learn more. Spend some time exploring the quaint boutiques and stores, full of homemade crafts and even stop in a witch store or a traditional apothecary. Make sure to get a photo with the Bewitched Statue downtown.
Gloucester Maritime History
Discover the incredible maritime history of Gloucester and the wider north Massachusetts region. Dating back to the landing of the pilgrims in 1620, Gloucester is America's oldest seaport, take a stroll along its beautiful and rugged coastline, tour the fascinating Cape Ann Museum and visit the 'Man Behind the Wheel' statue in the harbour, dedicated as a memorial to those lost at sea. Take a tour of its incredible Seafood Trail, where Gloucester showcases its local 'Ocean to Table' cuisine of fresh lobster, Crab, Clams and fish.
Stunning scenery in the Berkshires
Take a drive out to the jaw-droppingly beautiful Berkshire Hills in the western Massachusetts countryside. A favourite resort of 19th century wealthy vacationers, the area is still immensely popular thanks to a combination of forested mountains, fertile valleys, quaint villages and farms and incredible culture. Visit the Clark Institute of Art in Williamstown, play a round of golf at the large resorts or catch a concert at Tanglewood, the summer home of the Boston Symphony Orchestra. After a busy day of activity, relax and indulge with a gourmet farm-to-table meal in Lenox or Stockbridge.
Cape Cod and Martha's Vineyard
Cape Cod offers an enchanting blend of old and new, just two hours’ drive from Boston, Cape Cod offers a variety of opportunities to explore a unique coastal setting with vast sand dunes and pristine beaches. Martha's Vineyard can be easily reached by ferry from Falmouth and offers a slower pace of life and the perfect chance to go whale watching. On the island you'll find brightly painted ginger bread cottages and pristine beaches, you might even spot a few celebrities. These are two places we recommend you do not miss.
We recommend a stop in Nantucket, you'll love the quaint boutiques, art galleries and walking the charming streets along the waterfronts. After take in the incredible views and soak up the island magic.
"If you make the journey from Boston to the Berkshires, take the Mohawk Trail – there’s some truly spectacular scenery to see along the trail."
"Make the most of the tax free shopping throughout the state. There’s some great outlet malls too, including Assembly Row Outlets, that are perfect for finding designer treasures at discounted prices."
Tanglewood Music Festival
An iconic music venue located in the towns of Stockbridge and Lenox, Tanglewood plays host to the Boston Symphony Orchestra each summer. The Tanglewood music festival brings together a vast array of music, spoken word performances and conversations with prominent conductors and composers.
Throughout the first week of July, the city of Boston puts on a whole range of events to celebrate the 4th of July. As well as an impressive opening ceremony, there’s live music, a flag raising ceremony, the iconic Parade of Lights and a breathtaking fireworks display.
World’s Largest Pancake Breakfast
Each May, the city of Springfield celebrates its founding by throwing a huge pancake breakfast in downtown Springfield. Join in the celebrations and enjoy the delicious pancakes, coffee, juice and great company.
Boston Baked Beans
Massachusetts’ capital city is known by many as Beantown and its infamous baked beans are the reason why. Similar to the baked beans found elsewhere, Boston Baked Beans are usually cooked slowly, with molasses and bacon or salt-cured pork. You’ll find this dish on menus across the state, not just in the city.
Thanks to its coastal location and its historical reliance on its seaport, Massachusetts, like much of New England, is well known for its exceptional seafood. You can expect to find great seafood on the menu wherever in the state you go, including Clam Chowder and Lobster Bisque.
A Frappe is a similar drink to a milkshake but with the addition of several scoops of ice cream blended into the mix. It’s a sweet treat that’s beloved throughout the state, with all kinds of flavours, ranging from the classics to more creative concoctions.
Our Massachusetts destinations
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We've been tailor making holidays for 65 years. With over 60 destinations to choose from, talk to us and we'll listen to your travel ideas to create unforgettable holiday experiences.