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

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

Intertwined, interspecies trees which locals believe can grant boons to lovers.

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

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

While seemingly a cruel joke, this bench actually honors an esteemed member of the community who passed away in 2006.

This Civil War monument was designed by an eccentric architect and Gettysburg veteran.

This covered bridge was used by both Union and Confederate troops during the Battle of Gettysburg in 1863.

This monument marks the beginning journey of a wounded soldier's leg that ended up almost two states away.

Home of the only civilian casualty at the Battle of Gettysburg.

The beloved, war-tested mascot of a Union regiment graces their battlefield monument.

A diorama of the Civil War, fought by cats.

A dramatic, 360-degree recreation of Pickett's Charge in the Civil War.

New York's southernmost subway station is whimsically wavy.

The last living thing to come out of the rubble after 9/11 is now a symbol of hope and resilience.

The notorious headquarters of a corrupt political machine.

A little lighthouse in New York City, surrounded by mysterious stories of insanity-driven construction.

A former insane asylum despised by Nelly Bly and Charles Dickens is now fashionable apartments.

This outdoor gallery of graffiti-covered walls pays homage to the past, present, and possible future of street art.

This Wall Street bar was once a hub of revolutionary activity where Washington famously bid farewell to his troops.

A clock set into the concrete outside a Manhattan jeweler has been telling time underfoot for over a century.

This sculpture by artist Fritz Keonig survived the 9/11 attacks and now stands as a monument to the victims.

One of the most enjoyable bits of history at Coney Island and “the most romantic ride in the world.”

This whimsical group of statues is a favorite of children who love to climb all over Lewis Carroll's beloved characters.