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Top Massachusetts Road Trip Destinations – Tour Around & Enjoy!

Best Massachusetts Road Trip Destinations

Planning and exploring your own country is one of the most soul-satisfying feelings anyone can have in their lives. And it would even be greater to explore a new state with each trip. If currently searching for the next amazing destination to spark a lifetime memory, you won’t go wrong with Massachusetts. Check out our sampling of best Massachusetts Road Trip Destinations and have a time of your life!

The great state of Massachusetts has virtually any attraction you can ever think of. Whether you’re an enthusiast of music, art, colonial history, or simply want to experience the American adventure thrill while hiking, shopping, swimming, or tasting the delicacies of succulent seafood, Massachusetts State has it all! 

Being among the original thirteen colonies, this state has managed to preserve more than just its historic landmarks dating back to the pilgrim days. 

For a fun-filled expedition, check out the below slides for some of the best attraction sites to visit on a road trip around Massachusetts. 

Freedom Trail – Best of Massachusetts Road Trip Destinations 

The Freedom Trail road trip presents you with an opportunity to explore some of the oldest structures in American history. This is the topmost attractions of all the Massachusetts road trip destinations. This 3-mile-long trail is marked by some of the most iconic landmarks from America’s colonial era. The trail runs through the narrow streets of Boston then connects with 16 historic attractions and monuments. 

Freedom Trail - Best Massachusetts Road Trip Spots

On this trip, follow the brass medallions and red brick lines on the pavement, starting from Boston Common’s Visitor Center, then cruise all the way to the USS Constitution frigate at Charlestown Navy Yard. During this cruise, go through the two old cemetery grounds to see John Hancock and Paul Revere’s graves. 

You’ll also come across the oldest public construction in Boston, the Old State House, which is the ground where the Boston Massacre occurred when British soldiers murdered five colonists. A couple of steps from the Freedom Trail, you’ll come across Benjamin Franklin’s birthplace, 1 Milk Street. Other attractions you’ll come across during this trip include Faneuil Hall, Old North Church, and Paul Revere’s House. 

Norman Rockwell Museum – World’s Largest Rockwell Art Collection

Visiting the Norman Rockwell Museum located in Stockbridge gives you an insightful opportunity to see the largest Rockwell art collection on the planet. 

The museum was built in the name of Norman Rockwell, a talented artist in the 20th century. Apart from showcasing the artist’s works, this museum also puts on display some documents and photos as well as letters from the artist’s fans. 

Take a guided tour through the museums’ art gallery showcasing the artistry of Norman Rockwell and also learn a lot about his works and early life. If raising an aspiring artist in the family, this road trip is a great chance to ignite their passion and give them a reason to explore what they love best. 

Minute Man National Historical Park, Concord – American Revolution Site

Get to know about the American Revolution at this Massachusetts Road trip

This road trip takes you through the route used by British regulars when they trooped from Boston in a movement that gave birth to the American Revolution. Battle Road forms part of the Minter Man National Historical Park, in which Concord’s North Bridge is part of. The road is also the point at which the Colonials and the British engaged in a battle. 

The Visitor Center at North Bridge has some of the most interesting artifacts on display. Other items showcased include historical films and uniforms of the soldiers during the battle. At the bridge’s end lies the famous Daniel Chester’s Minuteman statue. 

Upon reaching Lexington’s Battle Green, you’ll also see another statue of the Minuteman and is the point at which the first gunshots were fired in 1775 on April 19. At Minute Man Visitor Center, you’ll learn about Paul Revere’s movement to warn colonists about the British advances. 

Fenway Park, Boston – Must-go for Red Sox Diehards

If you’re a baseball enthusiast or a Red Sox diehard, you wouldn’t want to miss this great opportunity of visiting Fenway Park. It is MLB’s oldest ballpark and home to the renowned Boston Red Sox. It is situated close to Boston’s Kenmore Square. 

With the help of a tour guide, take a tour inside the park and learn a lot about its rich history and how the Red Sox came to be. This trip also gives you the opportunity to view the park’s most unique features up close, such as Pesky’s Pole and Green Monster. It’s a great tour for families especially those with aspiring baseball players. 

Because we know you love Baseball so much, this is one of our top Massachusetts road trip destinations. Click a lot of pictures while you are there!

Cape Cod Area Beaches – Sand, Sea & Cool Breeze

Cape Cod Beaches - Best Massachusetts Fun Spots

Massachusetts has got plenty of attractions and fun-filled destinations to experience adventure thrill. One such place is the Cape Cod. The area has a wonderful beach that attracts visitors from across the country. 

The Cape Cod Beaches present a rejuvenating feeling, owing to the beautiful white sand and the sea waves bringing cool breeze to the shore. The beaches suit virtually any type of relaxation you seek and are full of outdoor activities, excitement, and fun for the entire family. 

Some of the beaches are best suited for surfing and are favorites among surfers seeking adventure, while others present magnificent sceneries and landscapes. One of the beaches you wouldn’t want to miss out is the Breakwater Beach best suited for families, Sandwich Town Beach best for scuba diving, and Sandy Neck Beach which has excellent views and beautiful wildlife. Cahoon Hollow Beach is a must-visit if you seek to chill out as you watch the beautiful sunset. 

The Historic Houses of Salem – Salem Witch Trials & More! 

While it’s common to come across historic homes with period furnishings in New England, only a few can stand up to the quality, variety, and number like those toured in Salem. Also, these houses represent a wide variety of history and culture of Salem. 

Salem Witch Trials from 1692 and House Seven Gables, which have been featured in Nathaniel Hawthorn’s book, are among the famous historic houses you’ll come across. These houses, together with the birthplace of Nathaniel Hawthorn are magnificently built and maintained and are open for visit by the public. 

Witch House of 1642, which served as Judge Jonathan Corwin’s home who is famous for presiding over witchcraft trials, is also among the historic houses here and is the only building construction remaining that has direct ties with the trials. 

Salem Maritime National Historic Site comprises two homes; Derby and Hawkes houses. The Peabody Essex Museum also comprises several famous historic houses, including John Ward House of 1684, Crowninshield-Bentley House of 1727, and Gardner-Pingree House of 1804. 

These historic houses represent a rich history of the “Old City”, and can best be explored on a Salem Morning Stroll Historical Tour. 

Nantucket – Romantic Getaway with Moonlight Cruises

Nantucket - Best Massachusetts Road Trip Spots to take romantic boat rides

If in need of a destination that best gives a conducive atmosphere for some romance, you wouldn’t go wrong with Nantucket. It looks ordinary but presents a nice environment to spend quality time with loved ones. 

There’s plenty of activities you can immerse yourself into, such as swimming, fishing, hiking, biking, and visiting museums. With an abundance of beautiful cozy lodges by the sea, it is an ideal spot to choose for a getaway. 

The serenity here is perhaps the reason why it is the country’s most popular and visited spot for vacations. 

Stellwagen Bank National Marine Sanctuary – World’s Best Whale Watching Site

This is among the top whale-watching sites on the planet and has the most biologically conducive ocean environment for productivity. 

The sanctuary is a plateau submerged under the Atlantic Ocean and rests at the entry of Massachusetts Bay. Here, various whale species can be spotted, as well as the white-sided dolphins of the Atlantic, seals, harbor porpoise among other aquatic animals. 

Over 50 different humpback whales live in these waters and have been named by the marine researchers here. Most of the whales are females bringing their calves for feeding and hunting at Stellwagen Bank. 

A perfect way to see the magnificence presented by this whale-watching site is boarding a whale watching tour in Provincetown or Gloucester which are closest to Stellwagen Bank. You might want to look for companies offering trained naturalists who can provide commentaries during the trip to help identify whale species and their behaviors.  As this is such a unique experience, it is one of the the most visited Massachusetts road trip destinations.

Tanglewood Concerts – Boston Symphony Orchestra

Best Concerts & Orchestra experience in Massachusetts

Music enthusiasts are definitely going to love this road trip to Tanglewood in Lenox, Western Massachusetts. As early as the 1930s, Tanglewood has served as the home to the famous Boston Symphony orchestra. Additionally, three other music schools are also located here, which makes it a perfect trip destination for those looking to advance themselves in music expertise. 

Boston University Tanglewood, Days In The Arts, and Tanglewood Music Center make Tanglewood boast with a reputation for nurturing talents in music. 

For this reason, Tanglewood is a known host of musical concerts and entertainment ventures that suit the taste of various lovers of music including classical, pop, and jazz. All you music lovers should have this on your itinerary as one of the top Massachusetts road trip destinations.

The Old Sturbridge Village, Sturbridge – Early Life of the 18th Century

This is a great one of a kind history museum which has, over the years, risen in popularity amongst tourists and those on educational trips. Old Sturbridge Village offers more than 200 acres for exploration, where you also get to enjoy learning a lot about the early life of the place dating back to the period between the 1790s and 1830s. 

You’ll also love the almost pristine historic setting of the place while learning about the life and history of rural New England. 

Wrapping up Massachusetts Road Trip Destinations

Massachusetts, as you might have noticed, is a land rich with lots of history. The city of Boston, in particular, has almost everything explaining the city’s tale. This trip is a perfect choice, especially if bringing kids along or perhaps for those who are fascinated by history. Bring your camera along and take snaps of those stunning views for a lifetime. However, visiting Massachusetts can be expensive, so have a look at our selection of wallet-friendly activities around the state.

Hope you loved our sampling of Massachusetts Road Trip Destinations, for a wonderful experience, book your vacation rental at RentalTrader.com. For any more information, fill our web form or give us a call, we will be happy to help you.

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