A man was airlifted to hospital with serious head injuries after a four vehicle crash.
The incident happen on the A66 near West Layton at 4.40pm on Monday.
A 21-year-old man from Ulverston, who was driving was a blue Vauxhall Corsa, was airlifted to the James Cook Hospital in Middlesbrough with serious head injuries.
A 32-year-old woman from Richmond, who was driving a black Ford C-Max, received treatment at the scene.
And a 42-year-old man from Wakefield, who was driving a white VW crafter pick-up, was also treated at the roadside.
The road was closed for four hours while emergency services were at the scene.
All four vehicles were travelling towards Scotch Corner.
And police are now appealing for witnesses.
Anyone with any information should call police on 101 and ask to speak to TC1768 Chris Coleman of the Richmond Road Policing Group.
Quote the reference number 12150129385.