Unless you live near one, you may not know that Massachusetts is actually home to many castles. Of course, these aren’t of the Medieval variety (mostly), but they’re still some of the most spectacular and enchanting structures in the state. This road trip will take you to the best of the best castles in Massachusetts with minimal planning on your part. All you have to do is hop in the car and prepare to be swept up by the magic of these majestic castles.

The road trip will take you about five and a half hours, and you’ll want to budget time to actually get out and take a look at these awesome sites. Check out the interactive road trip map here.

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1. Herreshoff Castle, Marblehead
Herreshoff Castle
You may associate Marblehead with seaside fun and old sailing mansions, but this coastal town is actually home to one of the most unique castles in the state. Built in the 1920s by wealthy artist Waldo Ballard, the castle is modeled after the 10th-century Viking castle of Erik the Red.
2. Hammond Castle, Gloucester
Hammond Castle
Flickr/Robert Linsdell
Perched on the rocky cliffs overlooking Gloucester Harbor, this remarkable castle is the former home of a wealthy and eccentric inventor who filled his castle with works of art from all corners of the globe. Today, visitors can take self-guided tours of the estate and explore places like the great hall, the courtyard, the Renaissance dining room, two guest bedrooms, the inventions exhibit room, the library, the war room, the kitchens, the servants quarters, and even a secret passageway. Learn more on the official website of Hammond Castle.
3. Crane Estate at Castle Hill, Ipswich
Flickr/Valerie Hinojosa

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Wikimedia Commons
This old mansion overlooking the ocean has an undeniable air of stately grandeur. The films "Flowers in the Attic" and "The Witches of Eastwick" were both filmed here, and the estate frequently hosts themed parties and weddings. You can tour the palatial mansion, and then wander down to Crane Beach for some time in the sunshine. Head over to the official website of Crane Estate at Castle Hill.
4. Bancroft Tower, Worcester
Flickr/Troy B. Thompson
Built just over 100 years ago by Stephen Salisbury III, this tower is 56 feet tall and one of the most dramatic spots in the area. It's open to the public, and visiting is free. Bancroft Tower would make for a pretty perfect picnic spot, or an amazing winter photoshoot destination. Read more about Bancroft Tower.
5. Searles Castle, Great Barrington
Wikimedia Commons/ John Phelan
Searles Castle has an interesting history. It was commissioned in the 1880s for Mary Hopkins by her husband, railroad millionaire Mark Hopkins. Tragically, Mark Hopkins died before the castle was completed. Mary then proceeded to wed her second husband, Edward Francis Searles – the designer of the castle's interior – while the home was being constructed. She named the castle after Searles. The structure has seven stories, 40 rooms, 36 fireplaces, and even a "dungeon" basement. The castle currently operates as the John Dewey Academy for troubled teens.
6. Searles Castle, Methuen
Wikimedia Commons/EraserGirl
No, that's not a typo. There's actually a second Searles Castle in Methuen, and even more incredibly, it's named after the same guy. After the death of his wife, Mary Hopkins, Edward Francis Searles built another castle...and named this one after himself as well. Today, the estate is home to the Presentation of Mary Academy high school. The school does occasionally open its doors to the public for tours, but even just checking out the exterior is a pretty great experience.
7. Winnekenni Castle, Haverhill
Wikimedia Commons/Beckwith-Zink (Diane)
This striking castle was built in 1875 by Haverhill chemist Dr. James R. Nichols as a summer home. Its name, "Winnekenni," is an Algonquin word meaning "very beautiful." After purchasing the estate in 1895, the city of Haverhill opened the castle to the public. Today, you can tour this grand estate and picnic on the sweeping lawns surrounding the castle. Learn more about Winnekenni Castle.
8. Ventfort Hall, Lenox
Flickr/Dave Rogge
This incredible estate actually houses a museum of the Gilded Age, where you can live your Downtown Abbey fantasies to the fullest. Built as a summer home George and Sarah Morgan (of the J.P. Morgan clan), Ventfort Hall was the center of the social season in the Berkshires in the 1890s and early 1900s. The house has 28 rooms, including 15 bedrooms, 13 bathrooms and 17 fireplaces. Public tours are available, and this castle is a popular spot for weddings and events. Go to the official website of Ventfort Hall.

What are your favorite castles in Massachusetts? Let us know in the comments! We profiled one of these castles as the most enchanting place in Massachusetts. Check out which incredible estate made the cut here.

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More to Explore

Castles in Massachusetts

Beth Price-Williams | September 25, 2020

What are the best road trips through Massachusetts?

One of the best ways to see Massachusetts is to hit the road. Nothing really compares to Massachusetts road trips. If you enjoy beautiful scenery, you’ll definitely want to follow the lighthouse road trip in Massachusetts. The road trip starts at Cape Cod Light and leads to several other lighthouses, including Nauset Light in Eastham, Chatham Light in Chatham, and Boston Light on Little Brewster Island. The waterfalls road trip in Massachusetts, on the other hand, is a must for anyone who loves waterfalls. You’ll travel to such breathtaking cascades as Doane Falls in Royalston, Wahconah Falls in Dalton, and Bash Bish Falls in the Berkshires.

What one-of-a-kind destinations can I visit in Massachusetts?

We can all find plenty of unique things to do in Massachusetts regardless of our interests. If you’re an animal lover, for example, you can’t go wrong with a visit to Animal Adventures Family Zoo & Rescue Center in Bolton. The zoo is home to exotic cats as well as toucans and alligators. Massachusetts is also home to a one-of-a-kind bridge park. Minute Man Historical Park lays claim to the historic and beautiful Old North Bridge. Stroll over the bridge and snap photos. The park is also picture-perfect for having a picnic and biking.

What are the most unique things to do in Massachusetts?

Some of the most unique things to do in Massachusetts also happen to be hidden gems. In fact, Massachusetts is brimming with hidden gems like the Brattle Book Shop in Boston. The huge bookshop features books both indoors and outdoors. Indoors, you’ll have three floors to explore. Gunn Brook Falls in Sunderland is an ideal destination when you want to spend time outdoors. Hammond Castle in Gloucester, Stockbridge General Store in Stockbridge, and Castle Hill at the Crane Estate in Ipswich are all unique destinations worthy of a visit, too.

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Featured Addresses
2 Crocker Park Ln, Marblehead, MA 01945, USA
Hammond Castle Museum, 80 Hesperus Ave, Gloucester, MA 01930, USA
Castle Hill on the Crane Estate, 290 Argilla Rd, Ipswich, MA 01938, USA
Bancroft Tower, Worcester, MA 01609, USA
Great Barrington, MA, USA
Methuen, MA 01844, USA
Castle Rd, Haverhill, MA 01830, USA
104 Walker St, Lenox, MA 01240, USA