A pair of giant roadside arrows are all that remains of a former Route 66 trading post.

A mysterious "wedding cake" castle in the middle of the urban desert.

This Route 66 classic sports a giant fiberglass rabbit that you can ride.

The story of Two Guns, Arizona could easily be described as a Shakespearian tragedy on Route 66.

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

An unexpected Easter egg lurks in the background of a cherub wall relief at the Breakers mansion.

This rare triple-jurisdiction drawbridge passes through Virginia, Maryland, and Washington, D.C.

Baltimore's classic clock tower was once topped by a rotating, 20-ton medicine bottle.

The longest continuous underwater road in North America was built at the insistence of Franklin Roosevelt.

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

A dark patch of the ceiling at Grand Central Terminal which was not restored is still stained brown by tobacco.

The site of the deadly Triangle Shirtwaist Factory Fire.

This historic address is home to the beloved ball and is an almost totally empty building among the most expensive real estate in the world.

The remnants of two World's Fairs are here, complete with a 12-story globe, a mini-Manhattan, and a UFO-shaped pavilion.

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

Once the tallest building in the world and the site of "the highest dinner ever held in New York" this building now holds the most expensive penthouse in the city.

A pedestrian island in the middle of world-famous Times Square emits a strange (and purposeful) humming noise.

An antique Beechcraft airplane serves as a giant windsock for people driving through the blustery open country of eastern Wyoming.

The high point on the 16th president's eponymous roadway is marked by a massive version of his head.

Surrounded by a hundred mile radius of billboards, Little America is a roadside attraction whose primary appeal is hospitality.

America's Most Wanted's set resides in this tribute to the history of crime and punishment.

The 5.5-mile ring of steel posts around the Capitol Building is one of the largest (and most uniform) of its kind in the world.

Look closely and you’ll notice that the color changes a third of the way up the tower.

An overlooked memorial honoring the local Washington residents who died in World War I.