An 11-year-old boy and a man were seriously injured when the motorbike they were riding collided with a car.
Emergency crews were called to the B4368 in Craven Arms, Shropshire, at about 1250 BST on Sunday.
The man, believed to be in his late 40s, was flown to Birmingham's Selly Oak Hospital with leg injuries.
The boy, who was a pillion passenger, was flown to Birmingham Children's Hospital with arm injuries. His condition was described as stable.
A spokesman for West Midlands Ambulance Service said the man and the boy both suffered "very serious injuries".
No-one else was injured in the crash.
The road was shut until 1800 BST. Police urged anyone who saw the crash to contact them.
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