The man, who was in his 50s, was travelling along the A167 on a Kawasaki motorcycle when he collided with man horsebox wagon and a Jaguar I-PACE, which were heading in the opposite direction.
He was pronounced dead at the scene of the crash, which happened at around 12.30pm on Sunday, near the Brompton Lane junction in North Allerton.
North Yorkshire Police has launched an investigation and officers are appealing for witnesses and information.
In a statement, the force said: "Officers would also like to hear from anyone with dashcam footage of the incident, or any of the vehicles in the moments leading up to it.
"Please contact North Yorkshire Police on 101, select option 2 and ask for Adam Elliott. You can also email [email protected]
"Please quote 12210138484 when sharing information."
The driver's identity has not been released.