The original air service was established in the late-1940s by Arthur Harjula with a single J3 cub. It was later named Stonington Flying Service when purchased by Herb Jones. When Herb’s son, Charlie, took the business over he renamed it Penobscot Air. In the early-1990s, Clint and Hannah Demmons bought the air service, retaining its name. In 1999, they sold to the Telford Group. In 2003, the Telford Group established the air service as Maine Atlantic Aviation. In 2004, the division was purchased by another individual, who retained the name Maine Atlantic Aviation.
In mid-December of 2004, the owner of Maine Atlantic decided abruptly to stop all service to the islands, and Kevin Waters decided to establish Penobscot Island Air. Service began with Kevin flying a single leased plane to the islands of Penobscot Bay.
It was a priority for Kevin to maintain the way of life for the people of the islands, whom he had grown to know very well while flying to the islands for the previous 11 years. To maintain flight service, it was a necessity to secure contracts to the islands, which he did. PIA holds the contracts for the U.S. Postal Service, Federal Express, Federal Express Ground, United Parcel Service, U.S. Forest Service, and U.S. Fish and Wildlife Service.