The collision occurred on Saltergate Bank, near the Saltersgate Inn, at around 1.30pm on the road that runs between Pickering and Whitby.
The male rider was heading towards his home town of Whitby when his black and blue AJS motorcycle came off the road to the nearside.
The man’s wife, aged 59, was following on another motorcycle, but she was not involved in the collision.
Ministry of Defence Police from RAF Fylingdales were the first on the scene to provide assistance before the emergency services arrived.
The rider was taken by air ambulance to the James Cook University Hospital in Middlesbrough with internal injuries.
The section of road remained closed until 5.20pm while the scene of the collision was examined by the police, with diversions put in place for motorists.
Witnesses to the collision are asked to contact North Yorkshire Police on 101, select option 2, and ask for the Roads Policing Group Scarborough. Alternatively, email [email protected], quoting reference number 12170176163.