It happened around 8 p.m. Wednesday night near the south entrance to the Sterling Road off of Route 1.
33-year-old Wyatt Weaver of Thomaston lost control of his pick-up truck as he traveled south and crossed over the center line before hitting another car driven by 21-year-old Brianna Widdecombe of Cushing.
Weaver and Widdecomb were both taken by LifeFlight helicopter to the hospital with serious injuries.
According to deputies, Weaver's vehicle was braking and sideways when it hit Widdecomb's vehicle head-on into its passenger side.
22-year-old Caleb Bixby was a passenger in Widdecomb's car and was taken to Miles Memorial Hospital for complaints of pain.
Both vehicles were totaled.
Deputies believe speed and alcohol were both factors in the crash.