The highway's southernmost spot is a beloved local attraction.

The sign that drew attention to a young boy's cucumber stand is now the name of his fruit superstore.

An idyllic swimming pool tells the tale of Hemingway's trouble with women.

An icon among Florida's pre-Disney tourist attractions.

This spiny beast guards an artist's village while vying for the title of largest lobster in the world.

St. Augustine's record-setting narrow street was designed to protect against pirates.

The walls of America's oldest masonry fort famously "swallowed" cannonballs.

A perfect circle of twenty-four mysterious holes dates back to prehistoric time.

A monument celebrating the idea of reaching inaccessible places.

Florida's oldest bar was once a morgue, complete with a hanging tree and gravestones.

A tribute to Ponce de Leon's supposed quest for eternal youth.

The former home of the Nobel Prize-winning American writer is now home to dozens of six-toed cats.

A luxurious 1880s hotel with its fair share of Tiffany stained glass, Edison electricity, and of course, ghosts.

A mysterious castle built as a monument to lost love.

Where manatees are the snowbird vacationers in these balmy Florida springs.

This 15-foot tall obelisk commemorating the Philadelphia-Baltimore railroad connection sat neglected for over a century.

America's most famous museum of medical oddities is home to the remains of Albert Einstein's brain.

The abandoned zoo enclosures offer a perfect place to experience the other side of the bars.

This building contains handprints that are well over a century old.

Once a gas station, this flightless airplane beside the Old Dixie Highway now houses a barbershop.

The highest point in Virginia can only be reached by passing through ponies and flowers.

The birthplace of Appalachia's only first lady, who some have dubbed the United States' "first female president."

Pennsylvania's own Roswell-style UFO mystery.

Steepest flood safety railway in the entire world.