In all of the 29 years it was in operation, no prisoners ever escaped successfully... or so they claim.

The world’s first penitentiary, meant to be humane, drove men insane.

A peculiar mansion built by the troubled heir to the Winchester Rifle Company fortune.

The Cape Cod house that whaling built.

All that remains of the once-booming chain is a single orange-roofed restaurant.

A massive Montreal stadium that has seen nothing but trouble since its inception.

This 1967 experiment in modular architecture was designed to be a new model for urban living.

The oldest continuously-operated inn in the United States, once owned by Henry Ford.

Two thousand artifacts from around the world collected by one woman who loved to travel.

Mrs. Mallard and her brood are a beloved fixture in Boston Public Garden.

A lighthouse on a diminutive island was one of the first of its kind to guide seamen home.

The American Revolution was galvanized into serious action due to the tragic clash with British soldiers that occurred at this location.

A former waterfront market is now in the center of town due to some interesting Boston engineering.

An interesting decoration on this historic site, this weathervane comes with as many legends as it does questions.

This nearly 200-year-old restaurant's history includes an exiled French prince, JFK, and a very hungry Daniel Webster.

The site of Paul Revere's historic two lantern warning.

Berthed at the Charlestown Navy Yard in Boston, "Old Ironsides" is the oldest commissioned warship still afloat.

This monument on Breed's Hill proves that one of the most famous battles of the Revolutionary War is misnamed.

The only structure left with direct ties to the Salem witchcraft trials of 1692.

The 340-year-old house that inspired the classic Nathaniel Hawthorne novel.

A massive sustainable farm designed by the mastermind behind Central Park.

Dispersed across 45-acres, 39 structures house a massive collection celebrating American Folk Art.

An eccentric inventor's castle home with its own indoor weather system.

The sweetest graveyard in the world is filled with headstones for dearly de-pinted ice cream flavors.