Open since 1938, this diner has kept its fountain, malt machine, and all the gum that greasers left beneath its counter.

This striking church was built from a Frank Lloyd Wright design more than a decade after the master architect's death.

One of two giant blue cockerel statues erected with an intentional double meaning.

A toweringly silly piece of modern art has been delighting locals since the 1980s.

This exemplar of modernist architecture is meant to captivate and inspire students of the Cooper Union.

The site of the deadly Triangle Shirtwaist Factory Fire.

The oldest living tree in Manhattan comes shrouded in sinister legend.

A strangely angled West Village home is the only monument to an explosion that took the lives of three American revolutionaries.

The notorious headquarters of a corrupt political machine.

The most confusing clock in New York.

Red frames showcase remnants of one of New York's original subway stations.

The only subway station in the city that still makes use of gap fillers.

The iconic Chicago sculpture hides a beautiful and easily overlooked plaque on the backside.

This ruined fort hidden at the top of Central Park can't seem to keep from losing its historical plaques.

Craggy concrete faces are hidden in the walls of this artificial cave along the San Antonio River.

A Manhattan office building is home to the world’s largest chess board.

New York City's first Modernist house.

Read a book next to a Midtown waterfall.

This unmarked and unloved Manhattan subway grate created one of the most iconic images in American cinema.

This bug-eyed water wheel uses the power of the Sun to clean up Baltimore Harbor.

Wedged between two sets of row houses is an awkwardly located family graveyard.

A faded sign from the 1920s remembers Baltimore's resistance toward banning alcohol.

A 200-year-old bar with a cheeky name claims to have served Edgar Allan Poe his final drink.

The building was originally a gas station built to resemble a Japanese tea house.