This Road Trip To The Most Majestic Castles Around Boston Is Like Something From A Fairytale

Whether you wanted to be a princess or prince, are charmed by all things royal, or are a fan of unique architecture, castles have a bewitching quality. Gazing at one conjures thoughts of fairytales, adventure, and days gone by. You may think that you have to head to Europe to view castles, but there are actually several much closer to home. We’ve arranged them into an entertaining road trip that’ll enchant the whole family.

The journey covers 96 miles and, if attempted on a weekend, takes 3 hours and 17 minutes without stops. You’ll find the map for the drive here.

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Tripadvisor/Vanesa C

Start your adventure with a visit to BU. This castle was constructed in the Tudor Revival-style, and you don’t need to be a student to scope out its exterior. The Castle does offer rental space for special events – something to bear in mind if you’re determined to turn your royal fantasies into a reality.

Address: 225 Bay State Road, Boston, MA 02215

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If you happen to visit Trader Joe’s in Newton, you’ll be surprised to notice that it sits in the shadow of an imposing, turreted building that once served as an armory. Although you can’t go inside, it’s a sight worth checking out.

Address: 25 Armory Street, Newton, MA 02465

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Facebook/Hammond Castle Museum

Huzzah! Here’s a castle you can actually tour. Hammond Castle Museum opens for the season in early May and remains accessible to the public through October. Those who visit this Medieval-style castle can embrace the fairytale and see a real drawbridge, an inner courtyard fit for royalty, and a secret passageway. If you like your stories darker, this place is supposedly haunted and the eccentric owner’s collections include Roman tombstones and a human skull! You can learn more about him in our previous article here.

Address: 80 Hesperus Avenue, Gloucester, MA 01930

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Wikimedia Commons/Daderot at en.wikipedia

You can stay in this castle, which operates as a seasonal B&B, or you can view the exterior from the street. If you ever wondered what Erik the Red's 10th century Viking castle would have looked like, this one is about as close as you can get – it was built following a detailed description of the Viking’s original home in Greenland.

Address: 2 Crocker Park Lane, Marblehead, MA 01945

Wikimedia Commons/Jameslwoodward

This armory is listed on the National Register of Historic Places. Constructed in 1893, the castle is an example of Romanesque Revival architecture and boasts crenellations and high towers.

Address: 36-38 S. Common Street, Lynn MA 01902

Flickr/Eric Kilby

This place may be a petite castle but it commemorates the fort, dubbed the Citadel, which once stood here. The Citadel survived assaults during the Siege of Boston and was a key fortification in the fight against the British. Now, this Gothic-style monument, which was built in 1903, serves as a reminder of the history made here. The flag on top is known as the Grand Union Flag, which was a precursor to the Stars and Stripes. George Washington personally raised a Grand Union Flag here on January 1, 1776.

Address: Prospect Hill Monument, 68 Munroe Street, Somerville, MA 02143

Facebook/Smith & Wollensky Boston Back Bay Steakhouse

You’ve probably passed by the armory that used to be the headquarters of Boston's First Corps of Cadets. This Romanesque Revival building, which dates back to 1891, now contains a suitably grand bar and restaurant called Smith and Wollensky. If you’re in the mood to indulge and unwind, a meal inside a castle should do the trick!

Address: 101 Arlington Street, Boston, MA 02116

What are you waiting for? Load up the car with friends or family then take this one-of-a-kind, castle road trip!