The man was driving a Volkswagen Polo which collided head-on with a green Peugeot 406 on the B1447 between Hawsker and Robin Hood's Bay just before 9.30am.
The male driver of the Peugeot had to be cut from his vehicle by Whitby firefighters and North Yorkshire County Council highways workers were also called to the scene due to oil being spilt on to the road.
A spokesman for the Yorkshire Ambulance Service told the Whitby Gazette it took both casualties to Scarborough Hospital via road ambulance – but the driver of the Volkswagen was later transferred to Hull Royal Infirmary.
The road was closed until 4pm to allow the wreckage and the debris to be cleared and to allow accident investigators access to the scene.
North Yorkshire Police were unable to comment on the condition of the injured man at the time of going to press.
Anyone who witnessed the crash is asked to call traffic constable 970 Mark Hutchings on 0845 6060247.