Grand Ole Osprey

The Grand Ole Osprey – Kent School’s 2026 Auction

Step into the charm of Ospreyland as we turn up the lights, the music, and the community spirit for The Grand Ole Osprey, Kent School’s signature fundraising event. Inspired by the legendary Grand Ole Opry, this year’s auction blends Nashville flair with Kent School heart—a night of live music, lively bidding, and joyful celebration.

Guests will enjoy an unforgettable evening featuring:
• Cocktails, food, and country-themed fun
• Live and silent auctions filled with exceptional items, experiences, and one-of-a-kind offerings
• Dancing and entertainment sure to get every boot tapping
• A mission-driven paddle raise supporting Kent School’s students, teachers, and programs

Join parents, alumni, faculty, trustees, and friends for a night of generosity, laughter, and Osprey pride as we celebrate Kent School’s history, its future, and the people who make this community soar. Mark your calendar, dust off your boots, and get ready for a spectacular Kent School tradition.

Together, we raise the paddle—and the roof.