You could be forgiven for thinking that Ichabod Crane School District must be located in remote country, high up in the mountains or down-wind of the Great Lakes due to the high number of snow days it has.  But actually, Ichabod Crane School District is the business name for the Kinderhook Public School District, who buildings are in Valatie, the flatlands above the Hudson River known for apple orchards. 

Urban Dictionary describes Ichabod Crane as  "to cancel something because of weather, even if the weather conditions aren't that severe. Expression originated in a school district just outside Albany, NY called Ichabod Crane Central School District ,which would cancel school for snow, even if there were two flurries, or better yet, even if there was no snow. Everybody in the Albany area wished they went to Ichabod Crane in the winter."

Reddit on "Why is Ichabod Crane Always Closed?"