1955
Orin Seybert founded Peninsula Airways. He was 19 years old, living in Pilot Point, Alaska and owned a 1946 two-seat Taylorcraft. In 1956, a four-seat Piper Tri-Pacer was purchased, and the company was named Peninsula Airways.

1965
On March 1, 1965 Peninsula Airways became incorporated and purchased the fixed base operation in King Salmon, Alaska which included the Chevron Airport Dealership.

1967
Peninsula Airways became a full-time subcontractor to Reeve Aleutian Airways, meeting Reeve's certificate obligations to the Chigniks, Perryville and Ivanoff Bay.

1969
Peninsula Airways acquired all assets of Tibbetts-Herre Airmotive, which had operated out of Naknek, Alaska since 1950. By 1973, regular service was provided between King Salmon and the Pribilof Island communities of St. Paul and St. George. Charter service was also extended into the Aleutian Islands in southwest Alaska, including Unalaska, Atka and Adak with Grumman Super Widgeon.

1977
Two Grumman Goose aircraft were purchased from Reeve Aleutian Airways, and the sub-contract was expanded to cover all locations certificated to Reeve throughout the Alaskan Peninsula and Aleutian Islands. This required setting up an operating base at Cold Bay, Alaska with hangars, offices and employee housing.

1980
The Civil Aeronautics Board awarded a Part 401 Certificate of Public Convenience and Necessity to Peninsula Airways, and all aircraft operations were conducted under Part 135 of the Federal Air Regulations.

1983
Peninsula Airways acquired its first turbine aircraft: a Cessna Conquest to be operated out of Cold Bay, Alaska. Peninsula Airways was the first Alaskan air carrier to qualify for CAB Part 419 subsidy, allowing the airline to perform Essential Air Service to Atka, St. George and Kodiak Island.

1985
Peninsula Airways acquired all assets of Air Transport Service, Inc., based in Kodiak. Included in the deal was a hangar and office facility with approximately six aircraft and scheduled year-round service to all points on the Island.

An Anchorage base was started with two Cessna Conquest turbo-props offering charter service from Anchorage to the Pribilof Islands.

1986
Scheduled service from Anchorage to King Salmon and Dillingham, Alaska was started with the Cessna Conquest.

1987
The first Fairchild "Metroliner" was purchased and put into service in 1987.  Through the next six years Peninsula Airways added additional Metroliners for a total of six aircraft.

1988
Several bush operators in Dillingham had their certificates revoked by the FAA, prompting Peninsula Airways to set up operation servicing rural Alaska. A hangar and aircraft were purchased and service to the surrounding communities began.

1989
Peninsula Airways was contracted by Exxon to support the "Exxon Valdez" oil spill cleanup. PenAir operations were inspected and approved by Exxon Corporation, U.S. Office of Aircraft Services, U.S. Department of Defense, and 2 FAA NASIP "white glove" inspections.

Alaska Regional Hospital awarded Peninsula Airways a contract to provide 24-hour medevac service between Alaska and the “lower 48” of the United States.

1991
Peninsula Airways began doing business as PenAir and became a code-share and mileage plan partner with Alaska based, Alaska Airlines.

1996
PenAir transitioned to FAA Part 121 regulations, operating under both Part 135 and 121. PenAir was the first regional airline in the United States to make the 10-19 seat required conversion, including an active dispatch department.

1997
PenAir acquired its first two Saab 340B aircraft servicing King Salmon and Dillingham, Alaska.

1998
Construction of a new hanger, located at 6100 Boeing Drive became home to both PenAir´s fleet and their corporate offices in Anchorage, Alaska.

2004
PenAir begins a Capacity Purchase Agreement with Alaska Airlines utilizing PenAir's crew and fleet in the Dutch Harbor/Unalaska market.

2005
Happy 50th Anniversary! PenAir is Alaska's largest commuter airline, operating a fleet of 40 aircraft (part 121 & 135) and providing scheduled service to 36 communities throughout Southwest Alaska. PenAir was the second airline in the state to receive the Medallion Shield Award

2007
PenAir constructs their second, 33,000 square foot hanger on Boeing Avenue in Anchorage, Alaska.

2009
PenAir expands into the Bypass Mail operation to include 5 new destinations. They also increased their fleet by welcoming their first "all cargo" Saab 340 aircraft.

2010
PenAir added its second "all cargo" Saab aircraft.

2011
PenAir increased their safety initiatives with their codeshare partner - Alaska Airlines.

PenAir, having a strong background in Safety initiates even strong policies and guidelines as one of Alaska´s leaders in aviation safety. As the provider of many of the Medallion Foundation´s procedures, these Safety policies are now being used, not just at PenAir, but implemented throughout the United States at many aviation facilities.

As a further commitment and standard of safety, PenAir, internally branded their central focus to be “Safety through Compliance”.  This empowered their employee group to not only think Safety first but to do so through compliance, achieving a greater understanding of the company´s many policies and assuring that all are being met.

This positive move also guided PenAir to a newer, fresher, streamed lined look with a new attitude, energy, dedication and branding, through a complete logo reface.

2012
PenAir was awarded two EAS (essential air service routes) in early 2012.  These routes meant expanding its operational base to the east coast of the United States with services from Boston to: Presque Isle, Maine and Plattsburg New York.  PenAir also picked up the seasonal summer route from  Boston to Bar Harbor, Maine.