Daryl was born on April 8, 1944, the oldest son of Harold “Eagle” Middlebrook and Florence Blair Middlebrook. Harold “Eagle” Middlebrook founded Penn Yan Aero in 1945.
Daryl grew up at Penn Yan Aero, learning to fly at a young age and soloing on his 16th birthday. He attended Penn State University where he obtained a degree in Aircraft Maintenance Engineering in 1964. He was a licensed Airframe and Powerplant Technician with an FAA Inspection Authorization, a Designated Airworthiness Representative for the Federal Aviation Administration, a Designated Manufacturing Inspection Representative, and an Instrument rated Private Pilot Land and Sea. He was a recipient of the Charles Taylor Master Mechanic Award for lifetime contributions in the field of aviation maintenance.
Daryl took over Penn Yan Aero in 1966 and focused exclusively on Lycoming and Continental engines. He pioneered numerous FAA Approved procedures and engine upgrades. Penn Yan Aero became known as the engine people and grew to be recognized as an industry leader in engine performance.
Daryl’s son, Bill took over Penn Yan Aero in 2006 and continues the family’s ownership and management.