Five people were injured, three critically, in a horrific early morning head-on crash in Gloucester on a highway bridge over the Annisquam River.

A 19-year-old woman, and two men, one 18 and one in his 80s, were listed in critical condition Monday, according to a statement from the Gloucester Fire Department.

Police arrived at the crash scene on the A. Piatt Andrew Bridge on Route 128 after 1:45 a.m. and found one car flipped onto its roof. Two people were trapped in the cars and had to be extricated by firefighters at the scene.

“Last night’s serious crash on the Route 128 bridge has deeply affected our community. My thoughts are with all those involved, and with their families, friends, and loved ones during this incredibly difficult time,” said Gloucester Mayor Greg Verga in a statement.

“This hits especially close to home, as several of those involved are not only from Gloucester, but are young members of our community. We are a city that cares deeply — we’re all holding those impacted in our hearts right now.”

The 18-year-old man, once freed by rescuers from a smashed vehicle, was moved to a safe landing site and flown by helicopter to a hospital in Boston in critical condition, according to officials.

Three other passengers, two women, 19, and the man in his 80s, were transported to Beverly Hospital. One of the 19-year-old women was then transferred to Tufts Medical Center in critical condition. The victim in his 80s was transferred to Lahey Clinic in Burlington in critical condition. The other woman, also 19, was treated and released.

A fifth victim, an 18-year-old man, was transported from the scene to Addison Gilbert Hospital where he was treated and released.

The crash remains under investigation by Massachusetts State Police.