Connecticut State Police said Robert Wetherbee, 76, left his Rangeley home Thursday to drive to North Windham, Connecticut, but never arrived there.
Wetherbee also went missing last year in a similar situation, and was found asleep in his truck in Massachusetts.
Wetherbee is described as 6'1" with blue eyes, and 180 pounds.
According to Connecticut State Police, he is believed to be driving a blue Ford F-150 pickup truck.
Anyone with information is asked to call Connecticut State Police at 860-465-5400.