Begin Application


Do boarding schools celebrate halloween?


While not all boarding schools celebrate Halloween, many do! This spooky holiday is a favorite for many students, especially here at Cheshire Academy, one of the oldest boarding schools in America. With a history that dates back more than 200 years, we have a few ghost stories to tell.


Halloween becomes a campus-wide extravaganza at Cheshire Academy, one of the best boarding schools. A tradition here at the Academy is that teachers and students typically dress up in costumes during the school day. There are, of course, rules that need to be followed for costume etiquette, but you will most definitely find goblins and ghouls roaming the hallways. Costume judging will take place for the best, most creative, or scariest costume, sometimes followed by a parade of ghosts, vampires, and other spooky creatures.


Our library staff sponsors Halloween activities, like creating spooky cards on a green screen,  and the dining hall gets into the mix, offering a Halloween-themed dinner. Faculty members even open up their homes for students to go trick-or-treating (costumes required).

A campus favorite is the haunted trail that takes place after dinner. Faculty members join forces to create a creepy journey through the back fields.Those students brave enough to face the woods at night, filled with haunted characters, will ultimately find themselves  at a faculty home for a Halloween party.


Each boarding school may have a different way to celebrate holidays like Halloween, but chances are, there will be an opportunity to get into the spooky holiday festivities.

Stacy Jagodowski

Written by Stacy Jagodowski

Ms. Jago joined the Cheshire Academy community in August 2013 as the director of strategic marketing and communications. Prior to coming to Cheshire Academy, she spent six years working in communications offices at both colleges and private school, as well as five years in admission at both boarding schools and day schools.

Most Popular Posts

Get new blog posts emailed to you!