Massachusetts Road Trip: History, Ghost Stories and Coastal Charm

There’s something magical about a New England road trip. Maybe it’s the postcard-perfect villages, the historic waterfronts or the colourful stories that seem to lurk around every corner.

Our final stop on a two-week, six-state journey through New England took us to Massachusetts, but not before a brief detour into neighbouring New Hampshire. From the maritime beauty of Portsmouth to the haunting history of Salem and the timeless appeal of Boston, this stretch of the journey proved to be the perfect finale.

Portsmouth: A charming beginning

 

Although technically in New Hampshire, Portsmouth deserves a place on every New England itinerary.

One of America’s oldest working ports, the compact waterfront city is wonderfully walkable. Market Square is filled with boutique shops and cafés, while Prescott Park provides sweeping views across the Piscataqua River. Check out the Love Wall and if you’re organised, bring a lock, but it not, just enjoy the view of the Memorial Bridge.

The city’s handsome brick architecture feels distinctly different from many of New England’s timber towns, and its maritime heritage is evident everywhere you look.

A leisurely lunch overlooking the harbour offered the perfect excuse to watch tugboats glide along the river before continuing south towards one of America’s most intriguing destinations.

Salem is more than witch trials

Mention Salem and most people immediately think of witches.

But while the infamous 1692 Salem Witch Trials remain central to the town’s identity, today’s Salem is much more than its dark past.

Salem is celebrating its 400th anniversary in 2026. Yes, you read that right. Salem turns 400 years old this year. That’s old when you consider that Boston doesn’t turn 400 until 2030.

The Salem Witch Museum provides one of the most compelling introductions to the tragedy. Through dramatic storytelling and historical records, visitors learn how fear, superstition and mass hysteria led to the execution of 20 innocent people within just a few months.

Rather than sensationalising the events, the museum encourages visitors to reflect on how prejudice and misinformation can have devastating consequences – lessons that remain remarkably relevant today.

It is interesting that for a long time, nobody in Salem wanted to discuss the witch period. It was an embarrassment, and it was only in the 1970s when Bewitched, that popular TV sitcom, was filmed in Salem that witches became popular.

When the sun goes down…

If Salem is fascinating by day, it becomes deliciously atmospheric after dark.

We joined an ‘After Dark Murder and Mystery’ tour with Witch City Walking Tours. Guide Topher Williams took us through the city’s historic streets, revealing another side of Salem. Hidden alleyways, former jails, centuries-old cemeteries and stories of smugglers, pirates and unexplained happenings combine to create an unforgettable evening.

We saw what was the old witch jail, where many of the accused witches were held, and also the old death row. We heard about George Washington’s brush with a ghost at the Merchant Inn, and plenty more fascinating stories. As we were there on Friday the 13th, it did feel extra spooky!

Whether you believe in ghosts or not almost becomes irrelevant. The storytelling alone makes these tours one of Salem’s standout experiences.

A city that embraces individuality

One of the biggest surprises wasn’t the ghost stories.

It was the people.

Salem has become one of America’s most welcoming and eclectic communities. Witches, artists, historians, families and curious travellers all mingle happily along Essex Street. The atmosphere is inclusive, colourful and refreshingly free of judgement.

It gives the city an energy unlike anywhere else in New England.

Beyond the witches

While the witch history draws visitors, Salem rewards those who stay longer.

The House of the Seven Gables offers insight into both literary history and the city’s complex maritime past, while the excellent Peabody Essex Museum showcases world-class art, culture and history in an architecturally stunning space. We loved the Anila Quayyum Agha: All the Flowers Are for Me exhibition, the East India Marine Hall,

For first-time visitors, the Salem Trolley Tour provides an excellent overview before exploring on foot.

There are many excellent places to eat, drink or shop, including Kakawa Chocolates, The Chocolate Pantry and Ye Olde Pepper Candy Company – the oldest candy company in the US – it has been sweetening up the lives of locals since 1806! Crow Haven Corner is the oldest witch shop in town and check out Witch City Broom Company, just in case you want to ‘ride’ back to your hotel.

Where to stay

Our favourite accommodation was Hotel Salem, perfectly positioned in the heart of the pedestrian-friendly historic district.

Stylish interiors, a lively rooftop bar, comfortable loft-style rooms and an unbeatable location made it one of the standout hotels of our entire New England journey.

Being able to simply step outside and immerse ourselves in Salem’s vibrant streets was a major bonus. The staff were so delightful, and the vibe relaxed and friendly. We opted for dinner at the rooftop bar, as it had such a lovely atmosphere.

Finishing in Boston

No Massachusetts road trip would be complete without Boston.

America’s revolutionary history comes alive along the Freedom Trail, while Quincy Market buzzes with restaurants and street performers. Whale-watching cruises, the Boston Public Library, the Museum of Fine Arts and the Isabella Stewart Gardner Museum easily fill several days.

Sports fans shouldn’t miss historic Fenway Park, while anyone looking for a slower pace will enjoy strolling through Boston Common or cruising the city’s picturesque harbour.

Boston effortlessly combines centuries of history with a youthful, energetic atmosphere, making it the perfect ending to an unforgettable New England adventure.

Why Massachusetts should be on every New England itinerary

From centuries-old ports and fascinating museums to ghost stories, world-class dining and vibrant waterfronts, a Massachusetts road trip offers far more than many travellers expect.

Whether you’re captivated by Salem’s haunting past, charmed by Portsmouth’s maritime heritage or inspired by Boston’s rich history, this corner of New England rewards travellers who take the time to slow down and explore.

For us, it was the perfect conclusion to one extraordinary American road trip.

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Planning your own New England adventure? Explore the rest of our New England road trip series for insider tips, scenic drives and unforgettable destinations across six remarkable states.