Chapter One of Becoming Teddy Roosevelt
by Andrew Vietze

A Man to Know

As darkness fell on September 7, 1878, Bill Sewall opened the door to find Theodore Roosevelt standing on his porch. Wearing big spectacles and weighing a scant 135 pounds, the Harvard junior looked both boyish and bookish staring up at the tall Maine guide. Sewall had been expecting Roosevelt and his companions—cousins West and Emlen Roosevelt and his friend Will Thompson—and he ushered them into his big, white-clapboarded farmhouse, which sat square in the middle of Island Falls, Maine.
Built just a few years prior, the Sewall House was not only at the geographic center of the tiny community of some 230 souls in the woods of Aroostook County, but was also its social center, and it was ever a busy place. Four Sewalls lived in its seven bedrooms, and they were frequently joined by another resident or two as well as visitors popping in and out, often looking for their mail. This was the town’s post office, its only guest house, and arguably its finest house; there was always something in the oven, and visitors were made to feel welcome. The city boy would be swept into a small-town world the likes of which he’d never experienced.
Through TR’s bespectacled eyes, Sewall must have been an imposing figure, filling the door frame, six foot four, healthy and strong at thirty-three. The first white child born in the pioneer town of Island Falls, the Maine guide had spent his entire life in the woods. When he shook your hand you knew it—he had bear-sized paws that were strong and calloused. In background and bearing he was very much like the heroic adventurers that Roosevelt had so idolized as a boy. With his red-tinged hair, full beard, and deep gray-blue eyes, he looked like King Olaf, the hero of Longfellow’s Saga of King Olaf—TR’s favorite poem. He was the kind of confident, no-nonsense man you’d follow into battle.
For his part, Bill Sewall had certainly seen more rugged specimens than this aspiring hunter, and he wasn’t particularly impressed. The boy in front of him looked like a "thin pale youngster with bad eyes and a weak heart," he would later write, who would "guffle" and wheeze due to his asthma.
To be fair, Roosevelt was exhausted by the time he reached Island Falls. He had spent the entire day traveling, having left the small train depot at Mattawamkeag, Maine, at ten that morning. Fifty-eight miles to the north and east of Bangor (itself a good two hundred miles from Boston), the outpost of 356 citizens boasted the last train station on the European and North American line, built eight years prior, and it was as remote as remote got. Step off the platform at Mattawamkeag, and you walked into a frontier as real as the one being opened up out West. Anyone wanting to head into the North Woods to visit Island Falls would make the rest of the journey by buckboard, and it would take the better part of six or seven hours to do it. By the time TR reached the front porch of the Sewall House, he had some miles on him, and despite the excitement and activity swirling inside the house, very shortly after arriving he climbed the stairs to the third floor, settled himself in a field bed, and fell asleep.
Not only had Roosevelt spent a long day traveling, but he wasn’t feeling well, in either body or spirit. The guide wasn’t far off in his initial assessment of the young man. Roosevelt’s heart was, if not weak, at the very least sick. The boy had suffered from a fairly severe case of asthma since he was a toddler, and he had endured an attack earlier in the day. This was before the dawn of inhalers, and these wheezing fits were genuinely menacing, taking a lot out of him. But there was more troubling TR than that.
Seven months earlier Roosevelt’s father, Theodore Roosevelt, Sr., a giant in his son’s life, had succumbed to a gastrointestinal tumor, and the young "Teedie," as he was called at home, felt the pangs of his passing as others might feel hunger. The two had been particularly close, the senior Roosevelt having been a stabilizing influence on his son, a constant source of strength and counsel. Without him TR felt rudderless, and he’d been despairing for the entire summer. And then, just a few days prior to his leaving for Maine, on a trip that he’d be planning for two years, his best friend, Henry Minot, perhaps the most supportive and sympathetic of his Harvard chums in his time of grief, walked out of his life, too.9 Minot’s father had withdrawn him from Harvard. By the time he arrived in the North Woods, Roosevelt was not only exhausted but bereft. "I feel very sad," he wrote in his diary that day.

Things were a little different the next morning. It would be hard to stay glum at the Sewall House. First, the place was alive with activity—people dropping by, Sewalls setting off for a day in the woods, meals being cooked and served. You couldn’t be in your own head for very long. And Bill Sewall’s family was a warm and hospitable clan, very attentive to their guests. His father, Levi, had started a tradition of helping and hosting the few visitors who made their way to Island Falls.
The first Sewalls in Aroostook County had had to toil endlessly to create their homestead, and sharing with neighbors and visitors had been necessary for survival. Once they were established in their wilderness settlement, they did everything they could to help those who followed.11 On the census forms in 1880, the Sewall House was described as a hostelry and Sewall listed his occupation as "hotelkeeper."
But it certainly wasn’t the sort of hotel Theodore Roosevelt was used to staying in. More a guest house with six residents, it had an open-door policy for hunters, and it was constantly filled with characters. Bill’s two older brothers were frequent visitors and quite a pair. "Sam was a deacon," Roosevelt would later write. "Dave was not a deacon." The loving touch felt throughout the home came courtesy of Bill’s mother and his sister Sarah. "Mrs. Sewall, the mother, was a dear old lady," Roosevelt recalled. "And Miss Sewall, the sister, was a most capable manager of the house."
Friends and neighbors came and went from sunup to sundown. Island Falls was a tightly woven community, and the Sewalls were among its most important threads. A local historian, who chronicled the foundings of each municipality in Aroostook County, would report in 1922: "[W]e have visited few towns where there is so general a community of feeling and such a genuine each-help-the-other spirit as in this town of Island Falls. Every man says his neighbor is the best fellow in the world, and I think they all tell the truth."
Roosevelt’s two cousins had experienced all this warmth and color before. They had visited a couple of years earlier, having headed north with TR’s then tutor, Arthur Cutler, for a hunting trip with Sewall, whom they had found by happy accident. Emlen was a year older than TR. He had a mind for business and was a trusted source of financial wisdom for his younger first cousin. A student at Columbia, West would become the Roosevelt family physician. All were close, and each one seemed to inherit an outdoor gene. Emlen would hunt—and correspond—with Sewall for years. West would go on to co-author a book called The Out of Door Library in 1897. The state of Maine was beginning to enjoy a reputation as a wilderness playground by the 1870s, thanks to the writings of Thoreau, the paintings of Frederic Church, and the coming of rail, which opened up the Maine woods as never before. Savvy entrepreneurs in places like Greenville were actively marketing North Woods adventures, publishing Baedekers like John Way’s Guide to Moosehead Lake and Northern Maine (1874) with its enticing maps, and aiming them squarely at the sports of the eastern cities.
Cutler and the Roosevelt boys were just the sort of men they were targeting, affluent and adventurous. They had already decided on a Maine trip when they ran into an acquaintance of Cutler’s at the train station in Boston, who told them the place to go in the North Woods was Bill Sewall’s at Island Falls. A quick glance at the map showed Island Falls to be just as northerly and deep in the wilderness as they wanted, and the well-heeled hunters were off.
At the time, the traditions of the Maine Guide were only beginning. As numbers of anglers and hunters from the urban centers of the Northeast began journeying to the North Woods for months at a time, they were eager for the services of men who could take care of them in the wilderness. In an attempt to attract sportsmen from away, the state legislature overturned an 1853 law that had outlawed hunting by nonresidents and passed new rules that allowed both hunting and fishing during the summer.
Bill Sewall had been guiding since he was twelve, and over the years had already developed a reputation as a "man to know." Arthur Cutler and his party stayed with Sewall about three weeks in the summer of 1876, enjoying themselves thoroughly. "I had the whole party to take care of, not to speak of the camp," recalled Sewall. "And altogether I had a pretty busy time and wasn’t able to give them as much attention as I wanted, but they got plenty of trout and went home satisfied."
TR had been captivated by the stories he heard from his cousins and his mentor and former tutor Arthur Cutler, and he couldn’t wait to make the journey into the Maine woods himself. Arthur Cutler understood Theodore Roosevelt well—he’d been teaching the boy since 1873—and he’d been on prior hunting trips with him and his cousins in the Adirondacks. A recent Harvard grad, Cutler was nine years older than TR, and Roosevelt’s father had hired him to help his son get into the prestigious Massachusetts university. Teedie would become the first graduate of the Cutler School for Boys (later the Cutler School), and Cutler continued teaching the sons of America’s elite for more than forty years; other famous alumni included J.P. Morgan and Waldorf Astor. He thought Bill Sewall might be a very good influence on the boy. The guide didn’t smoke or drink and he was a pious man, reading the Bible daily. He also had a quiet but persistent enthusiasm that matched Roosevelt’s own, putting his boots on each day with a zeal to get out and do. Cutler knew instinctively that the youngster he had spent so many hours with over the years would find the guide an appealing character, a Davy Crockett in the flesh, a living Daniel Boone. And he figured Sewall would be the type to help the boy get his head straight with the recent death of his father.
Cutler also understood that, because Roosevelt would probably take to Sewall, he’d likely be eager to please him. But he recognized that TR was more vigorous and capable in his head than he was in his body, so he asked the guide ahead of time to go easy on the kid. "I want you to take that young fellow, Theodore, under your special care," he said. "Be careful of him, see that he doesn’t take too hard jaunts and does not do too much. He is not very strong and he has got a great deal of ambition and grit, and if you should take such a tramp as you are in the habit of taking sometimes, and take him with you, you never would know that anything ailed him. If you should ask him if he was having a good time he would tell you he was having a very good time; and even if he was tired he would not tell you so. The first thing you knew he would be down because he would go until he fell."

On Roosevelt’s first full day in Island Falls, he arose ready indeed to get going, but this was Sunday, which for TR had always been a day of worship. As the hamlet still had no formal church in 1878, Roosevelt instead took a walk and read his Bible, memorizing the Nineteenth Psalm along the way. Bill Sewall was impressed when he heard about that. "Some folks read the Bible to find an easier way into Heaven . . . ," he observed years later. "Theodore reads it to find the right way and how to pursue it."
That afternoon Roosevelt walked down the road to a Methodist meeting at the local school, a simple, three-story, white-clapboarded structure with twin entrances and a chimney at the back. While he cleaned his spectacles and patiently waited for the service, he brooded about losing his best friend from Harvard. "Thinking about poor Hal Minot has again made me think much and oh so sadly of Father’s death," he wrote in his diary that night.
On Monday, the guns came out. Roosevelt had been given his first rifle at fourteen, and he’d done a fair amount of hunting in the backyards of his family’s summer homes—and in his travels to the Adirondacks and Egypt, where he’d bagged specimens for his growing natural history collection. But he had a lot to learn compared to the Maine woodsman and he knew it right away.
The young New Yorker spent the day hunting for partridge—commonly known as ruffed grouse. The chickenlike birds were frequently seen along the roadsides of Maine at that time of year, strutting and doing their nervous, hop-skip dance in the underbrush or roosting on a branch, but Roosevelt saw nary a one. His thoughts drifted back to his father.
By Tuesday, he was so busy that he didn’t have much time for sad reflection. He paddled downstream to Mattawamkeag Lake in a canoe with Wilmot Dow, Sewall’s nephew and fellow guide. The son of Bill’s sister Pauline, Will was twenty-three—just four years older than TR—and more of a best friend and peer to Sewall than a nephew. He had learned everything he knew at Sewall’s side and soon bested his uncle at most outdoor pursuits—the classic case of the gifted student who outgrows his teacher. Sewall recognized this and was more proud than bothered, calling Dow, "a better guide than I was, better hunter, better fisherman, and the best shot of any man in the country. . . . He was growing into a strong man, a master hand in all the ways of the woodsman."
Sewall, West Roosevelt, and the boys’ friend Will Thompson were in a bateau, a boat of the sort traditionally used by guides and lumbermen in the Maine woods. With a flat bottom and flared sides, it was more stable than a canoe for standing and pickpoling logs and could transport a large load of gear comfortably.
From Sewall’s house it was five miles down the fast water of the Mattawamkeag River to the lake, six square miles of pristine water, forty-seven feet deep and ringed by a forest of virgin spruce and hemlock. Sewall spent a great deal of time on Mattawamkeag and knew it intimately. He frequently paddled it—with guests and without—and he worked its shores for both game and timber. The river drained a vast watershed of swamps and streams, and it often was navigable even when other waterways dried up in the summer sun. The party paddled seven miles down the lake to its outlet where they set up their tents.
Getting out into the woods had a tangible effect on Roosevelt. After days in his funk, he finally "had good fun," tramping through the woods around the lake and taking potshots at pigeons and ducks. He and Emlen spent the following day doing much the same, shooting at loons and scouring the surrounding woodlands in search of partridge. They took one—after ten miles of walking—and TR’s spirits continued to rise. In his diary that night he mentioned both that he "enjoyed the walk very much" and that he and Emlen are "great companions."
Rain kept the hunters largely in camp for the next few days. They read, cleaned their guns, and played whist and euchre, card games of which Roosevelt was enormously fond, and dined on TR’s partridge as well as trout and pickerel, and ducks that someone else shot. TR and Emlen ventured out to spend a few hours at the confluence of the river and the lake, squatting behind bushes in hopes of surprising more ducks, but to no avail. Roosevelt did shoot a nighthawk and even a bat, but that was all. On Saturday he saw a duck, but missed on a long shot.

When the weather finally cleared, TR and Sewall took off into the woods together. Heeding the warnings from Cutler, the woodsman had arranged for his nephew Will Dow to take the other members of the party so he could focus his attentions on Theodore. He didn’t want the kid to hurt himself. They hiked fifteen miles in search of game, stopping to shoot at a couple of foxes sixty yards away. Roosevelt missed again, and he was beginning to get down on himself about his marksmanship. "I don’t think I ever made as many consecutive bad shots as I have this week," he wrote in his diary that night. "I’m disgusted with myself."
He wouldn’t get any more practice the next day, another Sunday. After studying his Bible in the morning, he spent the afternoon doing housekeeping—rather, camp-keeping—chores. But on Monday, Roosevelt and Sewall set out again. By now the guide had either chosen to ignore the admonitions of TR’s tutor or he had seen something in Roosevelt that gave him confidence, because the pair decamped on an extraordinarily ambitious trek—a thirty-mile walk along the Mattawamkeag River. They left at 8 a.m. and hiked for close to eleven hours, stopping only briefly to take lunch. As usual they hunted all the way, but for all his efforts, TR bagged only a single red rabbit, a merganser, and a pair of ruffed grouse.
At nineteen, Roosevelt was an intense, studious, and inquisitive young man, and he took these traits into the woods with him, along with a few habits some folks in Island Falls considered unusual, even odd. (One time, for example, he was so eager to catch a neighbor’s rooster that had gotten out of its pen, that he chased it up a ladder to the second story and into a stranger’s house, even crawling under the bed for it.) When he wasn’t hunting out in the woods, he was collecting. "He had an idea that he was going to be a naturalist," Sewall recalled later, "and used to carry with him a little bottle of arsenic and go around picking up bugs."
TR also had a font of energy as unstoppable as a rushing river—he always needed to be doing something. Sewall was used to clients traveling up to the North Woods to do some hunting and fishing, but they typically comported themselves as if they were on vacation, which translated to an easy pace and ample down time—as much relaxation as adventure. Young Roosevelt wanted none of that. On a few occasions, the guide suggested they pause and drop a line for trout, but TR declined. "Theodore was never very fond of that," Sewall remembered. "Somehow he didn’t like to sit still for so long."
They walked for hours and talked for hours, and in the woods around Mattawamkeag Lake Bill Sewall found his impression of Theodore Roosevelt changing. He’d kept a close eye on the boy since he’d arrived, just as the tutor had asked him to. "I did watch him carefully," Sewall would recall later. "He took a lot of watching. Yes, a lot of watching." And in doing so, the woodsman found that at least one of Cutler’s observations was true: "He’d never quit."
But he didn’t find the bespectacled city boy to be as soft as he expected. "He wasn’t such a weakling as Cutler tried to make out," Sewall explained. "We traveled twenty-five miles afoot one day on that first visit of his, which I maintain was a good fair walk for any common man."
Unlikely a pair as they may have been—the one a privileged, highly educated boy from New York City, the other a pioneer lumberman from the frontier—they bonded quickly. Arthur Cutler had known this would happen, and in fact it wasn’t all that uncommon for clients to bond with their guides. The woods have a way of making unusual allies—it’s usually love or hate because of the forced intimacy of close quarters and the teamwork required in remote settings.
But both Sewall and Roosevelt found that despite their many differences, there were more than a few similarities in their lives. Both had endured sickly childhoods. Both had a deep admiration for epic poems and adventure literature. Sewall was as much a fan of Sir Walter Scott and Henry Wadsworth Longfellow as Roosevelt was, and he was prone to lengthy recitations while he hunted (and even as he got dressed in the morning, for that matter). Even more central to their bonding, though, they discovered that both were constantly astonished by the poetry of the natural world. Not everyone who ventures into the woods can appreciate its subtleties.
The one complemented the other in an uncanny way. Sewall was an unusual backwoodsman—few if any of his logging peers could cite Marmion line for line, or would have been sensitive enough to reveal it if they could. Roosevelt was just as unlikely as a city boy—raised in the height of luxury, he was as comfortable sleeping on pine boughs in a canvas tent as he was on a feather bed in his Manhattan brownstone. Few men, backwoods bred or not, could match his zeal for the natural world.
"He was different from anybody I had ever met," wrote Sewall. "Of course he did not understand the woods, but on every other subject he was posted." The guide was clearly taken with his new friend. "Especially, he was fair minded. He and I agreed in our ideas of fair play and right and wrong. Besides, he was always good-natured and full of fun. We hitched well, somehow or other, from the start."

Now that he had a better sense of the young man, Sewall let him go out with Will Dow over the next few days. West Roosevelt went with them. Taking the canoe to the upper end of the lake in search of ducks, they shot through the marshy area there with "indifferent success," as TR put it in his diary. That meant they got a dipper duck and a wood duck, and when it came time to pull out and make camp they had a very "frugal" dinner.
The next morning they got up at four and resumed their hunt before the sun rose. Later in the day, TR took a ten-mile walk with Dow, shooting just four times. Even so, he came home with another merganser and three grouse—and a fondness for hiking in moccasins, which was something new for him.
He was at it again the next day, logging another fifteen miles in the woods, three of which were through a tangle of alders that made for terrain "about as difficult as any I have ever been through."36 He took a spruce partridge in a cedar swamp and another partridge on a hemlock ridge.
Perhaps because he was busy, perhaps because he was making new friends, perhaps because living outdoors fed something in him, Roosevelt began to move past the grief he had carried with him from home. References to his sadness became fewer in his diary, and he certainly didn’t voice any of his troubles. "In their company I would have been ashamed to complain," he’d say later. The playful spirit of his guides didn’t hurt. On one occasion they propped up a dummy bird for the eager TR to get a bead on. "Was nicely sold by the boys with a dead duck placed in a life like attitude," he duly recorded in his diary.
If he was reflective at all during the latter part of this Maine sojourn, it was not about the death that had so weighed on him just before his arrival, but about how much he loved being in the woods. "The leaves are now beginning to turn and the woods are perfectly beautiful," he wrote. "I have enjoyed this week very much; the trip so far has been a great success."
After spending two weeks in the bush, the party broke camp and started back to Island Falls on September 23. They piled into the boats, and Sewall paddled, Dow and TR rowed, Will Thompson trolled, and West and Emlen Roosevelt watched from the bow for ducks and loons. When they landed, TR spent the remainder of the day in the woods hunting with his cousin West.
During the next two days, Dow took Roosevelt out alone, first on a twenty-five-mile romp and then on a buckboard ride, searching for game all the while. During the course of these jaunts, TR bagged seven more grouse. Even though his tally of kills was lengthy by today’s standards—twenty-four animals over two weeks—he considered the hunting aspect of the trip fairly unsuccessful. "I have had wonderfully bad luck as regards shooting, finding very little game," he wrote in his diary. "But nevertheless have enjoyed the trip greatly. There has been absolutely no disagreement between any members of the party."

On Thursday, September 26, Theodore Roosevelt and his new friends parted. TR and his cousins took a buckboard back to Mattawamkeag station and boarded the night train for Boston. Roosevelt would return to Cambridge to resume his studies at Harvard, his comrades would continue on to New York.
Bill Sewall and Wilmot Dow went back to their normal routines in Island Falls, turning again to the projects that usually occupied them in the fall. They would have harvested their gardens, begun to ready their houses for the weather ahead, prepared for another season of cutting trees, and gotten back into the affairs of the town they were building out in the woods.
And they discussed the weeks past, unaware of their significance and the future they would portend. "At the end of the week I told Dow that I had got a different fellow to guide from what I had ever seen before," Sewall recalled. "I had never seen anybody that was like him, and I have held that opinion ever since."