An elected founding member of the National Academy of Design, Inman was well known in the New York City art scene.

The sweeping view of the northeastern American landscape coupled with the romantic depiction of an autumn afternoon shows the influence of the Hudson River School.

[3] Referencing the protagonist in Irving’s story, the painting’s teacher is Ichabod Crane, who is seen in the background at the schoolhouse's door.

At the left of the painting, is an African American servant, who in Irving's story, brought Ichabod Crane a note inviting him to attend "a merry-making" which led to an early class dismissal.

In Irving's story, the students "bursting forth like a legion of young imps, yelping and racketing about the green in joy at their early emancipation.

Contrasting with Irving's tale, Inman creates an idealized scene of childhood, the schoolchildren are simultaneously having fun while appearing to be well-mannered and peaceful.

According to art historian William H. Gerdts, Inman was known for his kind portrayals of people; "He made young mothers more radiant, and children more idyllic, and old men more benevolent."

With tinges of romanticism, Inman only portrayed the goodness in his themes, and encouraged other artists of his generation to “free themselves of rancor”.

[8] Over a century later, the painting was a part of "The Art of Henry Inman" exhibit at the Smithsonian National Portrait Gallery from April 2–August 2, 1987.

[18] Upon request, the Museum of Fine Arts loaned the painting to the White House for the duration of President Jimmy Carter's term, where it hung in the bedroom of his daughter, Amy.