Our 5 Day Road Trip to Massachusetts & Greater New England

Our 5 Day Road Trip to Massachusetts & Greater New England

There’s nothing quite like that feeling when you cross items off your bucket list! Matt and I finally took that long-awaited, much-anticipated road trip to Massachusetts and Greater New England. We visited Salem, Boston, and Gloucester, and spontaneously took a half a day trip to Portland, ME!

While there is a myriad of places I’m anxious to visit, Salem and Boston topped my list. And I don’t say Salem because I’m a kid at heart when it comes to Halloween (that’s only partially the reason). I have a soul-deep appreciation for American history and am beyond fascinated by it. Growing up in South Jersey, just outside of Philadelphia, America’s birthplace, I find it hard not to. Salem and Boston are beautiful historic cities that played a major role in our nation’s history. In addition to their rich history, they offer gorgeous architecture, excellent food, beautiful parks, and an energetic nightlife.

Let me get to it – Here’s everything we did while on our mini-vacation:

Salem, MA

Salem Witch Museum

We decided to make Salem our first stop and visited the Salem Witch Museum where we learned about the Witch Trials of 1692. It’s is the perfect start to a visit to Salem. It’s not the type of museum with exhibits and displays. Rather, they use stage sets with figures and a narration that tells the story of the victims of the witch trials.

Salem Witch Museum

The witchcraft hysteria in Salem first began in January of 1692 when a group of young girls, who later came to be known as the “afflicted girls,” fell ill and displayed strange behavior: hallucinations, fits and rages, hiding under furniture, and making strange sounds. The local doctor, Dr. William Griggs, examined the girls and when he couldn’t find anything physically wrong with them, he determined they must be bewitched. The girls went along with the doctor’s diagnoses and named people they believed were bewitching them.

The trials officially began February 1692 and lasted until May 1693. Over 200 people were accused of witchcraft and 20 people were executed: 19 victims were hanged and one was pressed to death. Two dogs were executed as well.

The big question was what caused this? More specifically, were the girls actually affected by something or were they faking it? Modern theory scholars suggest that the odd behavior stemmed from a combination of sorts, including ergot poisoning (a fungus), epilepsy, mental illness, asthma, child abuse, and stress. It’s also believed that some of the accusers were faking it.

Salem Witch Trials Memorial

We walked around the Salem Witch Trials Memorial, which pays tribute to the victims of the witch trials. The memorial contains 20 granite benches surrounded by a stone wall. The victims’ protests of innocence are inscribed on the stone slabs in the entryway.

Hocus Pocus House

How do you visit Salem and not see the house where the popular movie Hocus Pocus was filmed? The home is a private residence, so be respectful, although I’m sure they’re used to tourists checking it out.

Hocus Pocus House

The House of the Seven Gables

This house was made famous by American author Nathaniel Hawthorne’s novel, The House of the Seven Gables. 

The history of the house and its owners throughout the years fascinated me.  John Turner built the colonial mansion in 1668 and three generations of the Turner family occupied it before it was sold to Captain Samuel Ingersoll in 1782. Ingersoll removed four of the seven gables and several portions of the home. He died at sea in the 1800s and left the mansion to his daughter, Susannah, who was a second cousin of Nathaniel Hawthroen. Susannah told Nathaniel many stories about the home and its occupants. Nathanial was also inspired by the appearance of the house.  This led him to write The House of the Seven Gables. I never read that book (I purchased it at the gift shop after the tour), I loved his book, The Scarlet Letter. 

In 1908 Caroline Emmerton purchased the house, and with the goal of preserving the house for future generations, she transformed it back to its original seven gables, knowing the story would draw visitors. Hawthorne visited the house often. In 1910, The House of the Seven Gables opened to the public.

Emmerton used proceeds from museum visitors to fund The Houe of the Seven Gables Settlement Association, which helped immigrants adapt to their new life and offered services like classes and medical care.

As you tour the home you learn about Nathaniel Hawthorne and his works are showcased throughout the house. There are lots of artifacts, photographs, and framed works. The design of the house and the “hidden” entrances and how you can go from one room to the next is very interesting. Since the house is from the 1600s, it’s not as spacious as homes today and some of the doors and staircases are small and tight.

Ye Olde Pepper Candy Companie

Directly across the street from the house is Ye Olde Pepper Candy Companie, America’s oldest candy company. It opened in 1806 and is known for its old-fashioned candies.  You can find an assortment of gourmet handmade confections.

Derby Wharf Light Station

Also near The House of the Seven Gables is the Derby Wharf Light Station, which is part of in the Salem Maritime National Historic Site. The lighthouse was first lighted on January 17, 1871, and aided navigation in Salem Harbor. You can take a nice stroll to the lighthouse and the water. The lighthouse isn’t as tall or big as I expected. It’s twenty feet high and about twelve feet square.

Salem Common

We took a walk around Salem Common, a nice, clean 9-acre park in the heart of the city. It’s the ideal place to go for a walk or have a picnic and is pet-friendly.

Pubs and Restaurants 

  • Olde Main Street Pub
  • Major Magleashe’s Pub
  • Village Tavern Salem
  • Red’s Sandwich Shop (Reminds me of a diner, cash only)
  • Sea Level Oyster Bar & Kitchen (Excellent restaurant for seafood)

Boston, MA

Sam Adams Boston Brewery

For the love of beer, we had to visit the brewery. The tour is free and you learn about the beer making process and the story of how Jim Koch and two friends started Samuel Adams. You get a free beer glass and get to sample different beers. I learned that there are many Sam Adams beers that I have not heard of or tried and that’s because you cannot purchase them. You can only find them at select restaurants in Boston and order them there.

There is a tasting room which is ultimately a bar where you can buy beers and flights of beer, and play games and hang out.

Boston Tea Party Ships & Museum

The Boston Tea Party Ships & Museum tour is a must, especially if you have a strong interest in American history. After all, this historical event is often credited as being the spark that set off the American Revolution.

There are several parts to the tour. Live actors dressed as colonials discuss their frustrations and anger over the Tea Act as it violated the very reason they left England. This tax imposed by Britain on the colonies was the last straw for the American colonials and they revolted. They boarded ships, some disguised as Native Americans, and threw chests of tea into the Boston Harbor. You get to “relive” this by throwing chests of tea overboard. You also get to see the surviving tea chest and learn about its travels throughout time.


Cheers Boston

This is the Boston pub that inspired the fictional bar in the popular 1980s sitcom Cheers. The TV show was not filmed here but gives tribute to the show with menu items named after characters and a gift shop with Cheers merchandise. It’s a fun, entertaining environment with good food and beer.

Boston Common

Boston Common is similar to Salem Common in that it is a large park to take a walk or enjoy a picnic. You can walk the Freedom Trail which has a lot of historic markers that tell the story of the American Revolution.

Fenway Park

Home of the Boston Red Sox, Fenway Park is an absolutely beautiful baseball stadium. While it seems small from the outside, because it is next to the highway, it’s tall in size. Learning about its history, (it opened  April 20, 1912) and the changes and renovations over the years fascinated me.

What I found most interesting is the story of The Red Seat, located in the right field bleachers. This is where the longest home run was ever hit at Fenway, hit by Ted Williams on June 9, 1946. The ball struck fan Joseph A. Boucher, who was wearing a large straw hat. Fans who sit near this area wear a straw hat for this historic event.

Philadelphia Phillies 2008 World Series Team Signed Baseball

Gloucester, MA

Gloucester Fisherman’s Memorial

Built in 1925, the Gloucester Fisherman’s Memorial is an iconic eight-foot statue located on South Stacy Boulevard that gives tribute to those who lost their lives at sea. The statue is of a fisherman standing at the wheel of the ship.


Causeway Restaurant

For fresh seafood, or should I say the real deal, eat at Causeway Restaurant. The menu also includes Italian. They do not take reservations and it’s a little smaller in size compared to other restaurants, but certainly worth the wait.

Causeway Restaurant is where you will find the best New England clam chowder…EVER. Any seafood restaurant you go to in Massachusetts will probably be great, but this clam chowder, I don’t think you’ll ever have better.

Portland and Ogunquit, ME

Portland, ME is about an hour and a half drive from Boston so we decided to take a short trip up there. Portland is a beautiful city with lots of restaurants and shops and a historic feel. We took a short walk at a local park to enjoy the view.

Perkin’s Cove, Ogunquit

For a beautiful place by the sea, visit Perkin’s Cove in Ogunquit, ME. You can watch boats coming in and out and there is a small shopping center with mom and pop stores and restaurants. We had lobster rolls at Footbridge Lobster and they were delicious.
The only regret I have is not staying longer. We only visited for five days and by the end of each day, we were pretty beat since we did everything we could in a single day.

Have you traveled to Massachusetts or Maine? I’d love to hear where you went and what you did, and any suggestions on where we should visit!

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