Jack Trenhaile: Oral History Interview

This interview is with Jack Trenhaile of Hyland Estates. In this interview, Jack talks about becoming the vineyard manager at Hyland in McMinnville and his work over those 31 years.

Jack shares about growing up on a farm in northeast Nebraska, attending a one-room schoolhouse until high school, and then leaving home to join the Air Force. In 1968, Jack and his wife moved so he could attend the University of Hawaii, where he worked for a bookstore and started a hobby farm in their backyard.

Jack talks about moving back to Oregon in 1973, purchasing a farm in McMinnville, and hearing about “the vineyard up the hill.” After meeting the four owners of Hyland Orchard, as it was known originally, Jack became the vineyard manager on January 3, 1976.

Jack shares the early days of the Oregon wine industry, including working with other pioneers to prune and trellis the vineyard, attending monthly meetings at the Tigard Fire Hall, and digging up one of the first vines known to be infected with phylloxera. Jack was president of the company at the time of the sale in 2007.

This interview was conducted by Rich Schmidt at Jack’s home in Newberg on September 10, 2025.