The morning’s first flights aren’t dedicated to freight, but to transporting contractors to construction jobsites on the islands hours earlier than they would be able to arrive by ferry or chartered boat, which allows them to fit in a full day’s work. This morning, three men are headed on the under-ten-minute flight to North Haven to continue building a concrete retaining wall at a home there. And two walk-in passengers have come to ask about hopping on a flight to Matinicus, 22 miles from the mainland. These two men have arranged to help a Matinicus lobsterman, whom they haven’t yet met, to haul in his traps for the season in hopes of securing positions on his boat in the coming spring. One of those potential sternmen, from Mexico, Maine, mentions that he’s never been on a small plane before, or taken a flight of any kind. He’s bringing along a grocery bag full of frozen Hot Pockets. “You can warm them up on the boat’s engine,” he explains.

At 6:48 a.m., Sinclair tells me there’s a seat open if I’d like to ride along on a mail run with pilot Steve Turner of Rockport. I step outside and walk a couple dozen yards to meet him on the runway’s edge. In the dim light of the cloudy morning, he’s already removed some seats and loaded 123 UPS envelopes and boxes into the rear of the single-engine plane, to be delivered to North Haven, an island with about 350 year-round residents. Also climbing aboard is Tammy Brown, who says she’s lived on the island for more than 28 years and flies with the service often, this time on a return from an overnight visit with her daughter on the mainland. By catching an early mail flight, she says, she will get to her day job on the island on time. Her husband is already out on North Haven, which is where he was raised. I settle in just behind the pilot with my arm on a box holding a new Keurig coffee maker that’s going to someone on the island; behind me are 27 boxes of crystal glassware destined for North Haven Brewing Company. Before we leave the airport in Owls Head, Sinclair reminds Turner and the line techs to be careful with the fragile cargo.

After the plane rises from the tarmac of the Knox County airport, with its modern terminal and cafe and gift shop, Turner flies northward toward Rockland. I look down to see the purple-brown cast of trees that are well past autumn color—only a few small patches of snow so far—the gray-green surface of the water, and the linear Rockland Breakwater that is farther up the coast. We cruise to North Haven at an altitude of about 1,000 feet. The plane rumbles through some bumpy air before the pilot, who’s also a flight instructor, smoothly touches down on the longer of the two airstrips on North Haven. The crystal glasses are just fine.

Island-hopping history 

The runways on these islands are typically gravel, dirt, or grass and lined with trees, with adjacent obstacles such as open water, a road, or houses. Such conditions seem to be a natural fit for the cool-headed pilots flying these “SUVs of the sky,” as the Cessna 206 and Cessna 207 models are known. SUV is a good analogy, I think, when I see how these planes are being used throughout the day: people, pets, groceries, and packages are piled in as pilots move or remove seats when needed to get everything inside.

Waters has been a pilot with the flying service here since the 1990s, and eventually became the owner, by necessity. When the former owner abruptly stopped flying to the islands just before Christmas in 2004, Waters leased a plane and kept things going. Sinclair tells the story of how Waters took on ownership as a mission: “Kevin jumped in immediately because he thought, What about the people of the islands, who’ll need their medications and groceries and are expecting Christmas deliveries?”

And the islanders helped out, too. When service stopped, they held a meeting on Matinicus, and together the residents of the islands collected about $17,000 in cash to entrust to Waters as a “no strings attached” infusion to restart air service to the islands.

The mail and freight contracts help to bolster the business of the flying service, as does providing flights for the U.S. Fish and Wildlife Service and U.S. Forest Service for air surveys of wildlife, watersheds, land, and fisheries. Penobscot Island Air is also called for medical evacuations, which can be needed at any hour. “Like when a guy on Criehaven was playing with his phone,” Waters recalls, “and he walked right off the end of a dock, falling 15 feet into the water and rocks.” Sometimes the calls come at night, when the pilot—often Waters himself—may have to contend with high wind, runway lights that malfunction, or deer on the runways.

Waters feels humbled to be a vital part of the island communities and of Maine’s aviation history. And Waters thinks often of the future. He’s pleased to have brought on younger pilots like Robertson, who lives in Warren with his wife and five children, and Jeremy Harmon, who grew up near Portland and had previously piloted flights around Ellsworth and Mount Desert Island. “But when I first landed on Matinicus and saw the trees whizzing past,” Harmon says. “I knew this is where I wanted to be.”