Between the Clouds

A winter's day in the sky and on the remote islands of the midcoast with Penobscot Island Air and its fleet of single-engine Cessnas—to carry mail, passengers, and just about anything else that islanders may need

He may be the tallest pilot in Maine. Roger Robertson of Warren stands at 6 feet, 6 inches, or as he likes to tell kids, “5 feet, 18 inches.” But height isn’t really a benefit in the airplane, he admits. “I’m always bending to stay low, or get in.” Then there’s tiny Bijoux, the feisty Chihuahua in a sweater who must be one of the smallest dogs in the state’s aviation circles.

Robertson, Bijoux (the pet of a fellow pilot), several other men and women, and a couple of bear-sized dogs are all inside the dispatch and ticketing office at Penobscot Island Air at 6 a.m. on this late-November weekday morning. The sun’s not up yet, and a sparse show of snowflakes that won’t stick is swirling in the air above this small wooden building at the edge of the runways of Knox County Regional Airport in Owls Head, about three miles south of downtown Rockland. Inside, the building glows with lamplight and smells of coffee, and a stout yellow Labrador retriever named Maxie is wagging her tail at each person who comes through the door.

Dispatcher Sally Sinclair arrived before the others and stands behind a long counter, ready to review duty lists and let each of the pilots know where they’ll be going and what passengers and freight they’ll be taking. “The wind’s blowing 35 today,” she cautions, once the day’s three pilots have arrived.

The maintenance crew has prepped and pulled three planes from the hangars. The first task of one of the line service technicians is to drive to the Rockland post office to pick up the bins and bags of mail that the flying service transports for the U.S. Postal Service to the islands of Vinalhaven, North Haven, and Matinicus. Sinclair says that there’ll be a hefty load of freight today, since it’s the Christmas-shopping season. Adding to that, flights were grounded for a full day earlier in the week because of high winds in a fast-moving winter storm that also halted ferry service to the islands of Penobscot Bay for the day. Besides regular mail, the flying service holds the contract for FedEx and UPS deliveries to the islands, too.

“The islanders are masters of the internet when it comes to buying stuff online,” says Kevin Waters, who took over the service in 2004. “So the holiday season is almost busier than the summer—along with the medicines and groceries, there’s lots of dog food and the general ‘Amazon effect.’”

First of the day

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.”

Helping to carry and load people’s items into the planes’ compartments leads to familiarity and lighter moments, as when a passenger said to Robertson one day, “You’re always crushing the bread.” The comment baffled Robertson. He’s known to be a careful and thorough packer of mail packages and all kinds of freight for the island-going residents who climb aboard the Cessnas. “What bread?” he asked, not recalling the passenger having a loaf with him before. “In my backpack,” the passenger said, and pointed at the stuffed-full, zippered-up pack.

Then there was the guy who wanted to bring aboard a cardboard box of ice and beer: “Not waxed cardboard, or cardboard with a lining—just cardboard.” Robertson smiles as he recalls such flights. “What are they thinking?”

Curious cargo is part of the job, though. I notice four new tires and what looks like a car bumper wrapped in paper being readied for loading. Waters notes that, with the Cessnas, “We can take out all of the rear seats and load them with anything you’d put in a pick-up truck.”

Penobscot Island Air has moved flocks of geese and ducks to and from island farms, he says. And it was Robertson who was the pilot for a special mission last fall. A family moving off of Matinicus asked the company to bring their 250-pound pet pig to the mainland. It was a wild ride, flying with a pig in a crate, he says. “Every time you moved, it squealed.”

Pigs show up again in an Instagram post of Shawn Michaud, another of the Penobscot Island Air pilots. (Two summers ago, he was the easygoing, confident pilot who brought photographer Peter Frank Edwards and me out to Matinicus for a weekend stay.) Michaud posts on Instagram about his flight adventures with a from-the-cockpit viewpoint, including the time when two friendly island pigs sauntered right up to the plane after he’d parked on the Vinalhaven runway. Michaud’s humorous observations and peaceful video clips can be poetic: “I can usually be found in the sky, rolling around a cloud—but I am never alone.”

On the islands, I watch as packages and sacks of mail are handed to islanders who then make the final leg of the deliveries. On Islesboro, Dr. Pete Levandoski, a Brunswick dentist who travels frequently on the island flights, helps unload the freight before catching an afternoon ride back to the mainland. Wearing a high ponytail and sunglasses, Kate Adams drives a truck to meet mail deliveries to North Haven, then delivers house-to-house, bringing packages to residents who are happy to see her. “Every day is like Christmas,” she says.

Back in Owls Head, I meet the aviation company’s maintenance crew, two of whom are working on a winter project that’s far more involved than routine upkeep of planes. Eric Boyce and Sam Staples are inside one of the heated airport hangars crouched around the nose structure of the skeleton of a plane. The men are riveting together pieces of a Cessna 206 that they’re rebuilding to add to the fleet for 2019. Maintenance director Dave Staudt tells me that Staples is a skilled U.S. Navy veteran and “helicopter guy,” and Boyce is from Houlton and has been building and repairing planes for more than 50 years, including about 20 years in Alaska.

These are dedicated people and pursuits. Everyone at Penobscot Island Air works together toward a basic mission of island sustainability, according to Waters. “They aren’t just racking up flight time. These folks work hard and really care about the islanders,” he says. “Plus, you’re still scaring yourself sometimes. There will always be the chance of snowstorms and wind out there.”

The pilots experience it all inside planes that are often less than 30 feet from nose to tail, and only about a yard taller than most of them (less for Robertson), and they all say they love every flying minute.

Penobscot Island Air
By the numbers in 2018

7 | Airplanes in the fleet, mostly Cessna 206s and 207s
8 | Island destinations (Big Green Island, Criehaven, Deer Isle/Stonington, Islesboro, Matinicus, North Haven, Swan’s Island, and Vinalhaven)
14 | Pilots (six working full time)
600 | Average flight hours per plane
950ft | The shortest island runway on daily routes (North Haven)
10,000 | Passengers transported
14,000 | Take-offs and landings
500,000 | Packages delivered