A Party with a Purpose

By Jessica (Stephenson) Sharpe ‘03
Laughing Cavalier Coordinator

Special events are often called the “fun” of fundraising and Canterbury’s annual Laughing Cavalier is just that --- FUN. However, Laughing Cavalier serves a distinct purpose of garnering both financial support and awareness of the school’s excellent programming. Instead of a same old black-tie, sit-down dinner event, Canterbury has looked to create an experience that is both creative and exciting.

Laughing Cavalier began in the late eighties as a function to raise money for the school. The first four Laughing Cavaliers included comedic headliners such as Steve Allen, Milton Berle, Phyllis Diler, and The Second City. From there, the event evolved to include an auction element, yearly themes, and dancing; but nonetheless the name remained.

Throughout the tenure of Laughing Cavalier, the students and faculty have always been the focus. The event transports party-goers to a different time, era, or setting but proceeds to create an environment where it allows givers to experience a connection to Canterbury faculty and students. This connection is what has pushed Laughing Cavalier into a vital aspect of the Canterbury Giving landscape. With more than $6 million raised, Laughing Cavalier is more than just a party. The proceeds from Laughing Cavalier directly benefit the students, faculty, and programs of Canterbury School.

Like many aspects of the school, Laughing Cavalier would not be possible without the energy and expertise of a volunteer core. The mainstays of Laughing Cavalier year-over-year are the powerhouse of parents and school community members that lead the successful endeavor. Laughing Cavalier inspires the best, which is a direct reflection of the school community as a whole.

Even in the most challenging times, philanthropy for Canterbury School and Laughing Cavalier have been a central focus fundraising effort. The feelings during Laughing Cavalier 2021 Charlotte’s Web, held at Joseph Decuis Farmstead, could definitely be described as joyous as the Canterbury community united for an evening of high energy, entertaining auction, and an ambiance unlike any other.

Looking forward, Laughing Cavalier will continue to amaze and inspire, with the hope to carry on a tradition and spirit of giving and philanthropy for Canterbury School.