The schoolhouse where Jesse Merwin, the inspiration for the "The Legend of Sleepy Hollow" character, once taught.

At this farm in upstate New York, the former president plotted his reelection campaign.

A nearly 100-year-old dining car in upstate New York embodies the golden age of roadside dining.

This giant monument of the RCA mascot is a beloved fixture in Albany, New York.

Even in death, he's still your huckleberry.

The real-life site of Ichabod Crane's infamous gourd attack.

Oldest existing church in New York and the inspiration for Washington Irving's "The Legend of Sleepy Hollow."

In the middle of a busy airport, a statue honoring the astronaut who told Houston that Apollo 13 had a problem.

This depiction of the earth mother welcomes new life into Aurora Highlands.

One of the oldest art supply stores in the United States.

One of three remaining theatres in the United States created in the Art Deco Mayan Revival style.

One of the oldest continuously operating amusement parks in the U.S. is an open-air museum of Art Deco and neon lights.

Built in 1981 in collaboration with Andy Warhol, this giant piece of pop art stands on the campus of Colorado State University.

For 14 years, this former stray dog greeted every train passenger that arrived in Fort Collins.

This dynamic entertainment venue brings a much-needed funkiness to the region with its bizarre art, eclectic films screenings, and peculiar performance pieces.

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

Named for a prominent scout and explorer, this Wyoming state park encompasses a replica of an 1840s trading post, a 19th-century Army outpost, and early 20th-century automobile lodgings.

Evanston's historic railroad complex saved this rail town from reaching the "end of the line."

A sewing machine tycoon built this miniature castle for the people and to beautify a lakeshore.

At this site, two historic stone bridges spanning the Sing Sing Kill—one right on top of the other.

The home of one of America's most wealthy industrialists is now a historic site that remembers a more decadent time in the country's history.

This sound-art installation features songs composed using only the Mid-Hudson Bridge as an instrument.

The Brigadier General was so afraid of being buried alive that he had a buzzer installed in his mausoleum, just in case he woke up.

West Point’s only monument to a woman veteran stands above an empty grave.