Driver Killed, Two Passengers Injured After Vehicle Overturns at Cavalier Boulevard and Holland Boulevard [CHESAPEAKE, VA]

A man died Wednesday evening after a single-vehicle crash left a vehicle overturned at the intersection of Cavalier Boulevard and Holland Boulevard in Chesapeake, according to the Chesapeake Police Department. Officers were called to the intersection at approximately 7:33 p.m. on September 3, 2026, for a report of a crash. When officers arrived, they found an overturned vehicle with three occupants. The driver, a man whose identity had not been released as of this report, was partially trapped beneath the vehicle and was found unresponsive. Chesapeake Fire Department personnel pronounced him dead at the scene. Two passengers were removed from the vehicle and transported to local hospitals with injuries that were not life-threatening. The preliminary investigation indicated that no other vehicles were involved in the crash. The cause of the crash remains under active investigation. Anyone with information is encouraged to contact the Chesapeake Police Department Detective Bureau at 757-382-6251 or submit an anonymous tip through the Crime Line at 1-888-LOCK-U-UP or P3Tips.com.

The intersection of Cavalier Boulevard and Holland Boulevard carries traffic through the western portion of Chesapeake. Because police have not yet determined what caused the vehicle to overturn, investigators may review factors such as the vehicle’s movement before the crash, roadway conditions, witness statements, and other available evidence. The cause remains under investigation.

When a vehicle overturns in a single-vehicle crash, determining whether another party may bear legal responsibility depends on what the investigation establishes. Depending on the circumstances, evidence involving the vehicle, roadway conditions, or other factors may become relevant. At this time, authorities have not identified what caused this crash.

For the two passengers injured in this crash, potential legal options will depend on the circumstances established during the investigation. If evidence determines that another party’s negligence contributed to their injuries, they may have options through a personal injury claim under Virginia law.

Similarly, if the investigation determines that another party’s negligence contributed to the driver’s death, surviving family members may have legal options through a wrongful death claim. Whether such a claim is available depends on the specific facts surrounding the crash and what investigators determine caused the vehicle to overturn.

If your family lost a loved one or you were injured in a crash in Chesapeake or anywhere across Hampton Roads, Breit Law is here to help. With more than 47 years of trial experience, William Breit has fought for the families of crash victims throughout Chesapeake, Virginia Beach, Norfolk, and all of Hampton Roads — and he is not afraid to take your case to court. To speak with an experienced Virginia personal injury or wrongful death attorney, contact us today.

Sources:

• WAVY News 10
• WTKR News 3

Map showing Cavalier Boulevard and Holland Boulevard in Chesapeake, Virginia, where a driver was killed and two passengers were injured in a rollover crash on September 3, 2026.