From Fort Glenn’s airfield we would head west along the Pacific coast, then hop over the island to the geyser basin on the Bering Sea side, then back again to follow the bases of Recheshnoi and Vsevidof along the Pacific. The ocean side, peppered with black beaches on a ragged coastline, would offer tide pools, Cody’s favored habitat for exploration and discovery. The island also felt safe from Alaska’s biggest hazards: Umnak has neither bears nor large glacial rivers.

But danger did exist there. Separating the chilly Bering Sea from the warm Pacific Ocean, the Aleutians suffer the worst weather in the world. Always windy, often rainy, mostly foggy, the archipelago is known as the birthplace of storms. While winters rarely see subzero cold, summers are cool and cloudy. Like mountaintops above the tree line, the Aleutians support no trees or shrubs over knee high.

With hypothermia a very real threat, especially for a little boy, Umnak’s weather worried me. A one-piece Gore-Tex suit over long underwear and fleece pants and sweater would seal him in from the incessant wet wind. Pulling on his orange rain pants and jacket would protect him from a driving rain. I would fuel him with his favorite snacks kept handy all day, then quickly have him change into dry clothes each night for warm sleep. Our dome-style mountain tent would shelter us from gale-force wind and rain. And by tucking a copy of Charlotte’s Web into my pack to read aloud before bed, we could bring a little of home with us to the wild.

Full protection from Umnak’s weather was key, but the remoteness itself between Nikolski and Fort Glenn was a risk. Remoteness was not unfamiliar to us. We had driven for days across the Australian Outback when we would see few other cars. As a family, we’d day-hiked in the front country and backpacked for two and three days in the backcountry, including trips with grizzly bears and glacier river crossings. Keeping Cody safe would be simpler without bears or big rivers, but we would need to avoid accidents with a careful, cautious route choice.

Peggy encouraged our journey. She knew firsthand how time spent together in the wilderness strengthens bonds and relationships. And she knew that I would be sensitive to Cody’s needs and fears—looking after him, keeping him safe. But she also voiced her concern: “What if something happens to you?”

My answer begged her question: “Peggy, what could happen? I’ll be careful.”

“You said there are wild cattle. I don’t want you guys unprotected if a bull decides to charge. You should take a gun.” I packed a .44 Magnum.

The responsibility to keep both Cody and me safe from hypothermia, drowning, animal attacks, and injuries went without saying. But beyond safety, I wanted this trip to initiate a lifetime of shared wilderness adventures. For that, Cody needed a profound experience that he would want to repeat. Like most parents, Peggy and I replicated the positive aspects of our own parents’ child-rearing, tried to avoid the negative, and defaulted to the rest. If I wanted Cody to join me on future wild trips, then I needed to notice what interested him.

FROM THE DUTCH Harbor airport, Cody and I hopped in a taxi and met up with George Ripley, organizer of the first Wilderness Classic. At George’s house, out of the wind and rain, we talked about our trip. Our pilot, Tom Madsen, had been flying a big Japanese group of mountain climbers and their camera crew up and down the chain all summer. Every island hop needed multiple flights and there would be an empty seat the next morning. Madsen could drop us off at Fort Glenn on his way to the Islands of Four Mountains, just beyond Nikolski.

In the hangar the next day, the Aleutian guide Scott Kerr helped the Japanese team load up. We’d spoken on the phone but never met. He turned away from a mountain of gear to shake and hand me a six-inch aluminum tube, a fraction of an inch across.

“What’s this?” I asked.

“A tent-pole splint. I’ve been with the Japanese for over a month and they’ve climbed five volcanoes from Unimak to Umnak. But man-o’-man, the weather can get pretty fierce out here. The wind broke poles in three of their tents. Take this, for when the wind breaks yours.”

Cody and I followed the Japanese into Madsen’s brown twin-engine Beechcraft and crawled into a back seat. A stack of duffel bags and boxes stuffed in the tail crowded my shoulders and head. Cody sat on my lap with the seat belt buckled across us both.

Madsen bounced the plane off the tarmac and into the wind, headed for Umnak. A stormy low-pressure system would move in for the next couple of days, he warned, then it would clear up for five more. The news of good weather to come relieved me. After a short, bumpy flight, we circled Fort Glenn’s airfield. The ruins of the old military base stretched across the coastal tundra near Okmok Caldera. Madsen made a tight bank into the wind, then dropped and landed on the mile-long cinder runway. Cody and I hopped out. Madsen wrestled our single sixty-pound pack from behind the seats.

The wind blew stronger here than in Dutch. None of Fort Glenn’s original structures remained intact, save those whose four corners were anchored to the tundra by cables. The rest—walls, roofs, floors—had been gutted and scattered by Umnak’s incessant, erosive winds.

A sturdy guy in his mid-fifties, along with his wife and adult son, rode out on ATVs to meet the plane. Madsen exchanged mail and greetings with Fort Glenn’s only residents, then hustled off to fly his Japanese passengers to their next destination.

As the plane taxied away, I stepped forward. “Hi there, I’m Roman Dial.”

I hoped the guy had heard of me, maybe from an article about the Wilderness Classic in the Anchorage newspaper or Alaska magazine. Name recognition can help outlandish plans seem reasonable to strangers, but his skeptical look made it clear he wondered what the hell a man with a little boy was doing on a remote Aleutian island.

“I’m Gene Maynard. This is my wife, Rene, and my son, Cloud.” I shook hands with his family while Gene bent down to Cody.

“And what’s your name, little guy?”

“I’m Roman Two,” he replied, grinning.

What? I thought, startled. Up to that moment, he had always called himself Cody. I smiled broadly, choked down a giggle, wiped an errant tear from the wind.

“Roman and Roman,” laughed Maynard. “Well, what do you know! Come on up to the house, Roman One and Roman Two.”

From that moment on, Cody Roman Dial would introduce himself as “Roman,” a name Peggy, Jazzy, and I would address him by, too. Female relatives—grandmothers, aunts, and cousins—would continue to call him “Cody,” while my dad would call him “R2” in an affectionate attempt to differentiate us. At home, Peggy addressed “her two Romans” with a subtle yet unmistakable difference in intonation.

“Jeez, what ya got in here?” Gene wheezed, throwing my pack on his three-wheeler. “Hop on.”

Gene motored us to the ranch house, one of three intact structures at Fort Glenn. The other two were his sheds next door. An inch-and-a-half-thick cable anchored his house to the turf. Inside, their place was small and cluttered, like most cabins off the road system in bush Alaska—like my grandmother’s farmhouse, for that matter.

“So.” He looked me square in the eye. “What are you doing out here? Hiking around?”

“Yeah, I guess.” Gene and his family would be our first source of help should something go wrong. He needed to know our plans. “I want to walk to Nikolski. With my son.”

“Nikolski? That’s more than fifty miles away. You sure you wanna do that?” He looked down at Cody Roman. “That’s a tough crossing. I don’t know anybody who’s made it all the way.”

The skepticism in his voice rang all too familiar: like Dieter in Yosemite or Alaskan boaters hearing about packrafts. Once, a mountaineer even bet me and my Olympic-caliber partner a thousand dollars we couldn’t ski the length of the Hayes Range in less than a week. We finished in three days.

I deflected the conversation. “How about you? What are you doing out here?”

“Oh, we’re runnin’ a cattle business. There’s a couple thousand head of cattle brought out here after World War Two. All we gotta do is get the beef off the island.” He frowned as a gust of wind shook the house. “That’s the tough part.”

“How long you been at it?”

“’Bout six years now. But thinkin’ to get out.”

He circled back. “You know, there’s a couple o’ cowboys here who took horses out toward Nikolski. But they couldn’t cross the river. Had to come back.”

“River crossing, huh? I’ve crossed some rivers,” I said, feeling compelled to display some credentials, to tell him about swimming the Skilak or shouldering mountain bikes across a dozen rivers bigger than any between Umnak and Adak. But I knew this game well, mostly from losing. The more experience I claimed, the more desperate for acceptance I sounded, the smugger he would feel as a local. I kept my mouth shut.