Portland Private North Shore Historical Tour

Embark on an unforgettable private day tour from Portland, Maine, to the historic and scenic North Shore of Massachusetts! Start in the legendary town of Salem, where you’ll uncover its rich maritime past, explore the dark history of the Salem Witch Trials, and connect with the literary legacy of Nathaniel Hawthorne. Salem’s captivating history and coastal charm set the tone for an incredible day of exploration.
Next, step into history in Gloucester. An amazing seaport town. an optional tour of the stunning Hammond Castle, a medieval-style mansion perched on the coast. Then, visit Russell Farms for a taste of local fruit, wines, or apple picking in autumn. Our final stop is the grand Crane Estate in Ipswich, a magnificent seaside castle featured in Hollywood films. Before heading back, wander through Ipswich’s historic streets, home to one of the largest collections of colonial-period homes in America. This tour blends history, adventure, and coastal beauty—book your adventure today!

What's included:

• Hotel or AirBnB Drop off and Pick Up included.

Not included:

• Gratuities

What to expect:

Duration: between 8 hours and 10 hours

Salem Witch Trials Memorial

24 Liberty St, Off Charter Street, Salem, 01970, Massachusetts

Located just off Charter Street, on Liberty Street, is Salem’s simple yet dramatic memorial to the 20 victims of the witch trials of 1692. Four foot high granite walls surround three sides, with granite benches representing each victim cantilevered inward from the wall. Etched on each bench is a name, means of execution, and execution date. One can read, on the stone threshold of the memorial, words of the accused taken directly from court transcripts.

1 hour • Admission Ticket Included

The Witch House at Salem

310 Essex Street, Salem, 01970-3257, Massachusetts

This is the only surviving house in Salem that was a part of the Witchcraft Trials of 1692. It belonged to Judge Corwin, one of the magistrates in the witch trials. Witch House has been preserved in its original appearance. There are guided tours to see the house and learn more about what happened.

25 minutes • Admission Ticket Included

Bewitched Statue of Elizabeth Montgomery

Essex and Washington Street, Salem, 01970, Massachusetts

See the famous statue of Televisions most famous witch.

5 minutes

Old Burying Point Cemetery

51 Charter Street, Salem, 01970, Massachusetts

Salem's spookiest cemetery.

10 minutes

The House of the Seven Gables

115 Derby St, , Salem, 01970-5640, Massachusetts

The House of the Seven Gables, located in Salem, Massachusetts, is a striking example of Colonial American architecture, dating back to 1668. This historic mansion is best known as the inspiration for Nathaniel Hawthorne's famous novel of the same name. The house features a distinctive, dark wooden exterior with steeply pitched gables, hence its name. Visitors can explore its many rooms, including hidden staircases, large hearths, and period furnishings that reflect life in the 17th century.
The property also boasts beautifully landscaped gardens overlooking Salem Harbor, adding to its charm. The house's interior is filled with historical artifacts, providing a rich narrative of the families who lived there over the centuries. The site also includes Hawthorne’s birthplace, which was moved to the property in the 20th century, offering a comprehensive glimpse into both architectural history and literary heritage.

Pass by without stopping

Castle Hill on the Crane Estate

290 Argilla Rd, , Ipswich, 01938-2647, Massachusetts

At the Castle Hill on the Crane Estate in Ipswich, visitors will experience a stunning 59-room mansion set atop a hill with sweeping views of the Atlantic Ocean. The estate features beautifully landscaped gardens, intricate architecture inspired by Italian Renaissance villas, and the grand "Grande Allée," a nearly half-mile-long lawn leading down to the sea. Inside, the mansion showcases opulent interiors with period furnishings, fine art, and elegant details reflecting the grandeur of the early 20th century. The estate's history and breathtaking surroundings make it a highlight of any tour.

2 hours • Admission Ticket Included

Ipswich

Ipswich, Massachusetts

Ipswich, Massachusetts, is a charming coastal town steeped in colonial history and natural beauty. Known for having one of the highest concentrations of First Period homes (built before 1725) in the country, Ipswich offers a glimpse into early American life with its well-preserved architecture and picturesque streets. Its serene beaches, vibrant marshlands, and the scenic Ipswich River further enhance the town’s appeal, making it a delightful destination for history buffs and nature lovers alike.

35 minutes

Gloucester

Gloucester, Massachusetts

A quick stop in Gloucester, Massachusetts, offers the chance to see the iconic Gloucester Fisherman’s Memorial, which stands as a tribute to the countless fishermen who have lost their lives at sea. Known as “The Man at the Wheel,” this statue, located on Stacy Boulevard, overlooks Gloucester Harbor and symbolizes the town’s deep connection to the maritime industry. It’s a poignant reminder of the risks faced by generations of Gloucester fishermen, dating back over 400 years.
From the shoreline, you can also enjoy stunning views of Gloucester’s lighthouses, including Ten Pound Island Light and Eastern Point Light. Both are visible from various spots along the coast, especially from Stage Fort Park and the waterfront. The combination of the historic memorial and the picturesque lighthouses makes Gloucester’s harborfront a must-see, offering both a moment of reflection and breathtaking ocean views. Hammond Castle can be added on to any tour when in operation.

1 hour

Hammond Castle Museum

80 Hesperus Avenue, Gloucester, 01930-5273, Massachusetts

This stop is only available seasonally as hours vary. Admission is not included but it’s definitely worth the add on.

1 hour • Admission Ticket Not Included