Massachusetts' Hilltop Castle In The Berkshires Is An Idyllic Destination Pulled Out Of Medieval Fantasy

Though you might not expect it from a region settled after the medieval period, New England has a surprising number of castles. Many of New England's most timeless castles and mansions were built during the Gilded Age as America's new elite wanted to emulate the grand structures of Europe. Searles Castle in Great Barrington, Massachusetts, is a great example of these pseudo-medieval abodes, not only because of its sprawling size and chateau-style design, but also because it's suitably framed by the leafy views and charm of the Berkshires, an iconic New England destination. Due to its private ownership, you won't be able to go inside, but its location on a little hill on Great Barrington's Main Street makes it easy to see from outside and a worthy stop for lovers of architecture, history, and a bit of mystery.

Searles Castles was commissioned in the 1880s by Mark Hopkins, a founder of the Central Pacific Railroad, for his wife, Mary Sherwood Hopkins, though he died before construction even began. After his death, the castle was finished by architect Edward Searles (who built another Searles Castle located in New Hampshire). Searles and the widowed Mary Hopkins eventually married, though their marriage was rife with rumors and scandal.

Some say that Searles was having an affair with a servant using secret passages in the castle. Other legends go as far as saying that Searles poisoned his wife, and that she (along with the servant) continues to haunt the castle. While this is all hearsay, it is true that the castle holds an air of intrigue. Fortress-like walls surround the property, and Searles even designed a "dungeon" in the sub-basement. With its blue dolomite walls and spanning 54,000 square feet, Searles Castle is, even from a distance, quite a sight to behold.

Searles Castle has always been somewhat barred from access to the public. After its original ownership under Searles and Hopkins, it became a school for girls, then later a conference center, before ending up as a private residence again. Today, the castle is owned by artist Hunt Slonem. You can walk around the estate's border and get views of it from a sidewalk along Main Street. To reach Great Barrington, the closest airport with commercial flights is Bradley International Airport in Connecticut, about an hour and 20 minutes away by car. Visitors from Boston can reach the town in about a 2.5-hour drive.

While you're in town, Great Barrington is a lovely riverside escape with scenic trails and a thriving Main Street. Though you can't go inside Searles Castle, let alone stay overnight, there are some unique historical buildings in the same area where you can. One, the Wainwright Inn, is under a 10-minute walk from the castle grounds. Built in 1766, the inn has a long history as a tavern and later a colonial armory during the Revolutionary War. Another place worth stopping at in the castle's circuit is Saint James Place, built in 1911 (though its parish dates back to the 1700s). The stunning Gothic Revival building hosts community events, including concerts, lectures, and an annual model train display around Christmas time that you can't miss.

If you're interested in more of the history of the Searles Castle and the people who helped shape Great Barrington, the Great Barrington Historical Society and Museum, just a five-minute drive away, is a treasure trove of local lore.