5 Best Massachusetts Road Trips

From welcoming early settlers in the 1600s to being the birthplace of basketball and volleyball, Massachusetts has played a key role in the building of America’s foundations. So, it’s no wonder our favourite Massachusetts road trips are filled with historic sights and stories.

Stop by famous coffee houses, uncover ancient Native American trade routes and snap a few photos of legendary sporting sites.

With five road trips to choose from on our American Road Trip Planner, there’s something for everyone in Massachusetts at any time of year. Find your perfect route below.

Boston to Virginia: Shopping, Sights & Sidewalks

675 miles, 10 days, 12 stops

Fancy exploring the best of the East Coast? Running from Massachusetts to Virginia, this jam-packed road trip offers a mixture of history, shopping, nature and sport – perfect for a family adventure.

Starting in Boston, you’ll head to the city’s first Italian café, Caffe Vittoria. The locals call it the best coffee place in town, so be prepared to wait. It’s worth it though for the delicious Italian delicacies to have with your fresh cappuccino.

From here, it’s on to the famous Fenway Park – home of the Boston Red Sox baseball team. Tour one of the most well-known stadiums in the world, or if you’re here during the season, try and catch a game.

Then, it’s back on the road to popular sights like the Statue of Liberty, as well as mega malls and trendy shopping districts across Washington DC and Virginia for a browse of your favourite brands and independent boutiques.

Start your road trip in Massachusetts

Kentucky to Massachusetts: Cross-Country Sporting Successes

1157 miles, 10 days, 13 stops

Sports fans will delight in this road trip, taking in some of the most famous sporting spots across the northeast. Starting at the Louisville Slugger museum and factory and ending at Boston’s Fenway Park, this route has something to keep even the most die-hard sports fans happy.

Journey through Kentucky, Ohio, and Pennsylvania before heading into New York to visit the National Baseball Hall of Fame. After this, travel to Massachusetts to the Naismith Memorial Basketball Hall of Fame. Here, you’ll learn about the birth of basketball and how it became one of the most globally successful sports of all time.

End your trip with a tour of Fenway Park or catch a game if you’re there during the season.

Plan you cross-country sporting tour

Boston to New York City: Go Green for St Patrick’s

270 miles, 7 days, 8 stops

Planning a trip to Massachusetts in March for the annual St Patrick’s Day parades? Make a week of it with a road trip from Boston to New York City. 

New England has some of the best St Patrick’s Day celebrations there are in the US. The area became home to many Irish immigrants in the 1800s, and today hosts a huge festival to embrace the Irish traditions.

Visit key sights from Irish American history – starting in Massachusetts, where you’ll head to the Boston Celtics stadium, TD Garden. Grab a courtside seat to show your support or take a tour and see the Sports Museum.

While you’re staying in the city, follow the Boston Irish Heritage Trail through Downtown for a journey through years of Irish American history. You can then make your way to the Big Apple, via Rhode Island and Connecticut, to join the parades and hear stories from other Irish-American communities

Go Green for St Patrick’s

New York to Philadelphia: Haunted America

1208 miles, 14-16 days, 12 stops

Enter if you dare! This road trip is full of spooky sights, eerie goings on, and paranormal activity, so it’s not one for people who may be afraid of things that go bump in the night.

Starting at the Ghostbusters Firehouse in New York, you’ll head to various creepy places like the Sleepy Hollow Cemetery and Captain Grant’s Inn before heading to Massachusetts, famous for the Salem Witch Trials.

Head to Fort Warren first to see the ‘Lady in Black’ – a woman who made an ill-fated attempt to break out her husband imprisoned within the walls. Salem will fascinate anyone interested in witchcraft and history. Book yourself onto a Salem Ghost Tour or head to the museum to find out about the Salem Witch Trials and the puritanical history that made this town famous.

Discover Haunted America

Guilford to Portland: Captivating Colors

506 miles, 4-5 days, 10 stops

Whenever we think of Massachusetts, we think of fall and the changing leaves. What better way to see the seasonal shift than our Captivating Colors trip?

Starting in New Haven at Bishop’s Orchard, you’ll drive through some amazing scenery as you watch the leaves change.

The Mohawk Trail is our main stop in Massachusetts – a stunning way to watch the seasons change as you wind through the old Native American trade and travel route. Take your camping gear as there are plenty of pitches along the way or stay in one of the log cabins at Lamb City Campground. That way, you’ll be well-rested for the remainder of your tour through Vermont and New Hampshire.

Discover Massachusetts’ Captivating Colors

Massachusetts is home to stunning views, scary historical sites, and some of the most famous American sports venues. Pick a road trip and rent a car in Massachusetts with Hertz to discover the best this state has to offer.