One of America's first spies started out as a teacher in this little red one-room schoolhouse.

An abandoned 146-acre summer resort slowly being reclaimed by nature.

This lovely hilltop tower was specifically built to withstand 100 MPH winds.

A lone tower rises above the cliffs in a city park, offering fantastic views of the Connecticut landscape.

Holding multiple historical boats and an entire 19th century village, this New England attraction is the largest maritime museum in the world.

A former copper mine which became a truly unsuccessful prison.

Quirky castle designed by the American actor best known for portraying Sherlock Holmes on stage.

The former home of Samuel Clemens and family remembers the happiest period of the author's life.

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

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

Millions of numbers carved in glass represent the tattoos forced upon victims.

The history of the tea trade is told in bas-relief on this historic pair of Boston doors.

The headquarters of one of the world’s longest-running humor magazines bears a noticeable resemblance to a head wearing a Prussian helmet.

This supermarket is suspended 25 feet above an interstate highway.

This stone tower in a small town's graveyard looks as though it would be more at home in a fairy tale.

This giant Massachusetts sycamore is said to hold the dubious distinction of being the "widest tree East of the Mississippi!"

This railroad tunnel was once the longest in Massachusetts.

An iconic steel and chrome diner from the 1940s left empty for nearly 20 years is in danger of being demolished.

This classic red schoolhouse is said to have been where Mary and her little lamb went to school.

This iconic L.A. bookshop is housed in an abandoned bank—both symbolic and chic.

All that remains of this Massachusetts town, demolished in the name of progress, is a stone marker.

The monumental steeple on Amherst College's campus has no church attached to it.

A museum dedicated to the quirky and colorful world created by Springfield's favorite son.

One philanthropist's extensive collection of knick-knacks and curiosities is now a public museum of oddity.