A motorist was seriously injured in a crash on the B1264 between the Hornby junction and Low Worsall near the Cleveland border.
It happened at 9am on Monday and involved a black Skoda and a silver Audi.
Both drivers were taken to James Cook University Hospital.
The driver of the Skoda was released with minor injuries, but the driver of the Audi remains in hospital in a serious but stable condition.
Police are appealing for witnesses to the collision and anybody that may have seen the vehicles prior to the collision, to get in touch.
They are also appealing to anyone who may have caught either of the vehicles on private CCTV or dashcam along the B1264.
Anyone with information that could assist the investigation should email Traffic Constable Peter Keenen at peter.keenen@northyorkshire.police.uk.
You can also call North Yorkshire Police on 101, select option 2, and ask for Peter Keenen.
If you wish to remain anonymous, you can pass information to Crimestoppers on 0800 555 111.
Please quote the North Yorkshire Police reference number 12240021805.
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