The Washington County Sheriff's Department says it happened around 6:30 this morning on Route 1 near the Blue Bird Ranch.
Investigators discovered Luis Figueroa, 41, of Milbridge was trying to pass vehicles when he collided head-on with a dump truck driven by Dennis Smith, 65, of Jonesboro.
Figueroa had to be pried from his vehicle with the jaws of life and was later airlifted to Eastern Maine Medical Center with serious injuries.
Smith was less injured, but was brought in to be checked out for pain.
The busy stretch of Route 1 was closed while investigators documented the scene and looked for the cause of the crash.