The crash happened around 11:30 p.m. in the area of Route 13.
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According to Delaware state police, the driver of a Ford F-150 pickup truck was going southbound in the northbound lanes when his vehicle hit a northbound Toyota Tacoma.
The driver of the Toyota, identified as a 41-year-old Philadelphia woman, was pronounced dead at the scene. Two other occupants of the Toyota were pronounced dead at the hospital.
Police said they are still working to identify those victims.
The driver of the pickup, a 48-year-old man from Elkton, Maryland, was also pronounced dead at the scene.
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The names of the victims have not been released as police work to notify next of kin.
I-495 northbound between I-95 and Route 13 was closed for about five hours for the investigation and cleanup.
Anyone who witnessed the crash is asked to contact Master Corporal Breen by calling 302-365-8486.