Lured here by the promise of tens of thousands in gold, Jesse James started a quintessentially American trend of robbing trains in-motion.

A mysteriously dark cemetery monument fuels stories and legends galore.

For just a few bucks, this Iowa funicular will let you feel like an 1800s fat cat.

A hidden barn-sized rendition of Grant Wood's most famous, and most parodied, painting.

Home with Gothic windows featured in a famous painting.

A giant pair of thick black glasses mark the tragic demise of a trio of rock and roll legends.

A number of gruesome unsolved murders have turned this simple home into a morbid tourist trap.

This statue inspired by Renoir's famous painting embodies the jovial spirit of Key West.

An eclectic treasure trove of maritime marvels.

Disney's abandoned animal island is now an overgrown ruin that was almost the coolest attraction ever.

The former desk of Fire Chief Joseph "Bum" Farto is all that remains after his mysterious disappearance following a drug conviction.

This small museum is dedicated to the history of Havana and Florida's once-booming tobacco industry.

The only known working replica of the world's first self-propelled vehicle.

This creative sculpture was a way to "recycle" an old tree.

Though it's unclear why it's there, the lifelike sculpture of the giant lizard is oddly charming.

Working compound meant to allow visitors to reclaim the values and traditions of the past.

Get up close with some alligators at this roadside farm attraction.

It's believed Elvis Presley was inspired to write his breakthrough track after staying here.

The largest freshwater lake in the Florida Keys.

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

Leave it to Key West to drop a real-live drag queen instead of a ball to mark the arrival of the New Year.

The ruins of a creative scholar's fantastical unfinished sanctuary act as his massive gravestone.

One of the largest Native American shell middens stands 30 feet tall.

The ruins of a once massive plantation are now a private residence hidden in the Florida wilderness.