Police are seeking witnesses following a crash on the B1257 near Helmsley.
It follows a collision between a white Mercedes Sprinter van and a black Mitsubishi L200 pick-up near the bottom of Sproxton Bank on Thursday at around 6.30pm.
Following the crash, the driver of the Mitsubishi, a man in his thirties from the Helmsley area, was taken to James Cook Hospital, Middlesbrough, with serious injuries where he remains in a serious condition.
Three children also travelling in the Mitsubishi were taken to York District Hospital.
Two have since been discharged while the third remains in hospital following treatment for a broken arm.
The driver of the Mercedes, a man in his forties from the County Durham area, was taken to York District Hospital where he is in a serious condition.
Police want to speak to anyone who witnessed the collision or saw either of the vehicles before the crash.
Anyone with information is asked to contact North Yorkshire Police on 101, select option 2 and ask for Traffic Constable Steve Wood or email firstname.lastname@example.org
Please quote incident number 12130210863 when passing on information about this collision.