The man was killed when the crash happened on the A41 in the north of the county shortly before 4pm on Saturday.
An air ambulance was sent to the scene near Market Drayton along with paramedics, police and firefighters but the biker was pronounced dead at the scene.
A woman who was driving one of the cars involved was left trapped and had to be cut free by fire crews before being taken to hospital. The extent of her injuries is not yet known.
Four other people were checked over by medics and discharged at the scene.
All three vehicles suffered significant damage in the crash, which happened at Rosehill near Stoke Heath Prison, a fire service spokesman said.
The A41 was closed between Tern Hill and Wistanswick throughout Saturday evening as collision investigators examined the scene.
A spokesman for Market Drayton Fire Station urged people not to speculate on the cause of the collision while the investigation takes place.
They wrote on Facebook: "On arrival at the scene the crews found that an RTC had occurred which involved two cars and a motorbike, all three vehicles had sustained a significant amount of damage in the collision.
"An ambulance crew were on scene and were engaged in carrying out CPR on an adult male casualty.
"Crews immediately began to stabilise the vehicle and set up hydraulic cutting and spreading equipment to release the trapped female.
"The Midlands Air ambulance from Cosford attended the scene carrying a critical care doctor and paramedic.
"Fire crews worked closely with paramedics to carefully release the trapped female driver using hydraulic rescue equipment, before she was transported to hospital via land ambulance for further assessment and treatment.
"A further four casualties were given assessments by the critical doctor and paramedics before being discharged without the need for hospital treatment.
"Tragically despite the best efforts of the critical care team and paramedics from West Midlands Ambulance Service the motorbike rider was pronounced dead at the scene.
"Our thoughts and prayers go to the family and friends of the motorbike rider at this very sad time.
"We send our best wishes to the female driver and hope that she goes on to make a full recovery from her injuries.
"If you were in the area of the A41 at the time of the collision and have any information or dash cam footage, then please contact West Mercia Police on 101.
"Please do not speculate on the cause of this collision, a full forensic police collision investigation is being carried out which will confirm the cause."
Firefighters from Market Drayton, Hodnet and Wellington were all sent to the scene.