Penobscot Island Air’s roots trace back to the late 1940s, when Arthur Harjula began offering air service with a single J3 Cub. The business later became Stonington Flying Service under new ownership by Herb Jones, and eventually renamed Penobscot Air when Herb’s son Charlie took the reins. In the early 1990s, Clint and Hannah Demmons purchased the business, keeping the Penobscot Air name until it was sold to the Telford Group in 1999. A few years later, in 2003, the air service was rebranded as Maine Atlantic Aviation. That name remained in place after a change in ownership in 2004.
In December 2004, with little notice, Maine Atlantic ceased all island service. In response, longtime pilot Kevin Waters stepped in and founded Penobscot Island Air to ensure that critical air service to the islands of Penobscot Bay would continue. With a single leased aircraft, Kevin launched operations in January 2005.
Kevin, who had spent over a decade flying to the islands, understood how essential air service was to island life. He quickly secured contracts with the U.S. Postal Service, FedEx, UPS, the U.S. Forest Service, and the U.S. Fish and Wildlife Service to ensure continuity of service. With support from island communities—most notably a $17,000 collection from Matinicus delivered anonymously in a brown paper bag—Penobscot Island Air was born.
Kevin Waters was the founder, heart, and soul of Penobscot Island Air. He passed away suddenly on July 5, 2020, at age 62, leaving behind a profound legacy. As Penobscot Island Air pilot Shawn Michaud wrote at the time:
“Some say there are angels among us, that they are put here to make our lives better… to show us what love and compassion are truly about. If this is true—and I have no reason to believe it is not—heaven took one home last night.”
Kevin grew up in Hampton, New Hampshire, and graduated from Winnicunnett High School in 1975, where he played varsity football and hockey as team captain. After high school, he found his way to the mountains of Lincoln, NH, and joined the ski patrol at Loon Mountain. During that time, he enlisted in the U.S. Coast Guard, serving in Key West, Boothbay Harbor, Woods Hole, and the Caribbean during the conflict in Grenada.
After eight years in the Coast Guard, Kevin followed his lifelong dream and attended flight school in Greeley, Colorado, earning his multi-engine, instrument, and helicopter ratings. He returned to Maine to fly for Atlantic North and Colgan Air before joining Penobscot Air in 1998. It was then that he began flying to the islands—and knew he had found his calling.
In 1993, Kevin married Terry Sinclair, a nurse he met years earlier while stationed in Boothbay Harbor. His love for aviation and dedication to the islands only grew stronger with time.
When island air service was unexpectedly suspended in 2004, Kevin jumped into action. With the community’s support, he established Penobscot Island Air—initially running flights out of a trailer with hay bales stacked around it for insulation. From those humble beginnings, he built a company that today flies passengers and cargo 365 days a year, with over 10,000 annual enplanements and a fleet that includes three Cessna 206s, two Cessna 207s, and an amphibious 206.
Kevin was more than a pilot or business owner—he was a friend, a leader, and a fierce advocate for the island communities. He made everyone feel seen, heard, and valued. As many who knew him will tell you, Kevin had a language all his own:
These expressions live on in the hangars, cabins, and conversations of Penobscot Island Air.
Someone once asked:
“How can a small company that moves people, boxes, and groceries in banana boxes be so special?”
The answer is simple: Kevin. His kindness, honesty, trust, and respect set the tone for everything and everyone.
After Kevin’s passing, Terry Waters made the commitment to continue the work Kevin began. With the dedication of what Kevin often called “the best crew ever”—pilots, schedulers, ground crew, maintenance teams, island drivers, and loyal customers—Penobscot Island Air continues to serve the communities Kevin loved.
As Shawn Michaud wrote:
“He will be a part of everything we do at PIA. He will be on every flight, overseeing every boat operation, mingling amongst all of you as you board your next flight, and in every one of our deliveries. Watch over us. Rest easy, Boatswain—we have the watch.”
Taking the helm in the midst of a global pandemic, Terry Waters guided the company through challenging times with the same dedication, integrity, and island-first mindset that Kevin exemplified. Under her leadership, Penobscot Island Air continued to serve as a lifeline for the islands, honoring Kevin’s vision of dependable, community-centered aviation. In October of 2024, Terry passed the torch to the Creeley family, marking a new chapter in PIA’s story.
With a home on Matinicus, the Creeleys understand firsthand the essential role Penobscot Island Air plays in the lives of year-round residents, seasonal visitors, and businesses alike. Their vision is grounded in a genuine appreciation for island life and a commitment to preserving the values that have defined PIA since its founding. With that spirit, they carry forward the legacy of Kevin Waters—ensuring that Penobscot Island Air continues to fly with purpose for years to come.