Kent School’s 2026 Auction
Welcome to Ospreyland
Saturday, March 28, 2026 | 6:00 PM
M.V. Mike Williams Gymnasium
Kent School, Chestertown, Maryland
Join us for a night of Nashville-style fun, community spirit, and meaningful giving.
A Night to Remember For a Cause That Matters
Step into Ospreyland as Kent School turns up the lights, the music, and the generosity. Inspired by the legendary Grand Ole Opry, The Grand Ole Osprey is our signature fundraising event — where country flair meets campus pride.
This unforgettable evening features:
- Cocktails and country-themed cuisine
- Live and silent auctions with exceptional items and one-of-a-kind experiences
- Dancing and entertainment that’ll have every boot tapping
- A mission-driven paddle raise supporting our students, teachers, and academic programs
Come together with parents, alumni, faculty, trustees, and friends to celebrate Kent School’s past, present, and bright future!
Together, we raise the paddle — and the roof.

