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On The Trail Of Benedict Arnold

May 2024
12min read

Some of the infuriating questions surrounding the great hero-traitor can be answered by visiting the fields where he fought. The trip will also take you to many of the most beautiful places in the Northeast.

No one has ever fully explored the inner geography of Benedict Arnold’s heart. The springs whence flowed his mad, desperate courage lie so close to the sources of his cynical, calculated treachery that the channels quickly merge, making it impossible to follow the bravery without being overwhelmed by the darkness—which leaves him, to our lasting fascination and bewilderment, among the hardest human beings to understand in American history.

Did he become a traitor because of all the injustice he suffered, real and imagined, at the hands of the Continental Congress and his jealous fellow generals? Because of the constant agony of two battlefield wounds in an already gout-ridden leg? From psychological wounds received in his Connecticut childhood when his alcoholic father squandered the family’s fortunes? Or was it a kind of extreme midlife crisis, swerving from radical political beliefs to reactionary ones, a change accelerated by his marriage to the very young, very pretty, very Tory Peggy Shippen?

Again, the inner geography is complex and extraordinarily murky. But there is another, fresher way to come at an understanding of Benedict Arnold—not so much by worrying about his inner geography as by viewing him against his “outer” geography, the American landscape he fought through during the three glorious years when his reputation rocketed up as steep and glorious a trajectory as any American military leader has ever known.

I may have been the last American ever to feel personally betrayed by Benedict Arnold.

Arnold, the “ferocious and ubiquitous Arnold,” the “best battlefield commander on either side during the Revolution”—the man who no less an authority than Lord Germaine, the British secretary of state, warned was “of all the Americans, the most enterprising and dangerous”—managed between the autumn of 1775 and the autumn of 1777 to accomplish feats that can only be described as astonishing: leading in person one of the most daring wilderness marches in the history of warfare; building the first American navy and using that navy in a battle that held off a British invasion for a crucial season; playing, a year later, a key role in what is generally agreed was one of the most important battles not only of the American Revolution but of world history.

Following Arnold through the landscape where these exploits took place is as good a way as any to approach the man in the light cast by his heroism. And since the “Arnold” landscape remains among the most lovely and unspoiled on the continent, a week or two spent following his path through the wilds of Maine, the drama of Quebec, and the splendors of Lake Champlain is a journey that, for pastoral beauty and historic interest, can scarcely be bettered.

Because geography played such a powerful role in Arnold’s rise to fame, it’s best to get a clear idea of the very specific corridor that obsessed him, the geographic puzzle he sought time and time again to solve.

The St. Lawrence–Richelieu–Lake Champlain–Hudson northern waterway leads from Quebec City, for so many years the Gibraltar of North America, into the deep, strategic heart of New York and New England. The military historian John Keegan refers to this as “the blood-stained warpath,” and well he might. From Samuel de Champlain’s first battle with the Iroquois in 1608 to Thomas Macdonough’s naval victory at Plattsburgh in the War of 1812, this was the scene of almost constant back-and-forth fighting.

Arnold’s operations along “the blood-stained warpath,” the geography that helped decide his fate.
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The best—and worst—years of Benedict Arnold’s life were spent here. He had been traveling back and forth to Quebec ever since he was a teenage trader (and smuggler), and even his eventual treachery, the selling to the British of West Point with its command of the Hudson, was an attempt to unlock this corridor by yet another means.

When Colonel Arnold arrived at Washington’s headquarters outside the besieged Boston in the late summer of 1775, he had already done his share of fighting along Lake Champlain; it was he who along with the equally courageous and quarrelsome Ethan Allen had surprised Fort Ticonderoga on the night of May 10 and won for the colonies its urgently needed cannon. Now here he was back in Cambridge, ready to carry out an audacious plan in what would be the first American offensive of the war.

While Gen. Richard Montgomery led an army up the “traditional” Lake Champlain route to the St. Lawrence toward Quebec, Arnold would lead his own army on a daring, surprise march through the trackless wilderness of Maine (then part of Massachusetts), forming the right flank of a pincers that would win Quebec—and Canada—for the rebel cause.

Arnold was given a thousand men (among them, a number who went on to become famous or infamous—Daniel Morgan, Henry Dearborn, and those future traitorous rascals James Wilkinson and Aaron Burr) and the challenge of sailing them up the Maine coast into the Kennebec River. There they were to board hastily constructed six-man bateaux to carry on the upriver trip to the Height of Land portage and the run down the tumultuous Chaudière River to the gates of Quebec. All that could be found for guidance was a map drawn by the British cartographer John Montresor in 1761, a map that Arnold didn’t realize had been purposely altered to deceive any potential enemies. Arnold, relying on this poisoned document, thought the distance his army would have to travel was 180 miles when it was actually more than 300, the first of the miscalculations and nasty tricks of fate that would dog the expedition right from the start.

My own fascination with Benedict Arnold began as a boy when I read the novels of Kenneth Roberts, particularly Arundel , which, in describing the march to Quebec, paints Arnold in a heroic monotone that, to a boy going through a rebellious stage himself, was immediately captivating. (It was only later that I read about his treachery; indeed, I may have been the last American ever to feel personally betrayed by Benedict Arnold.)

The street where Arnold was wounded still gives a good idea of what a formidable barrier his men had to storm.

My wife and I picked up Arnold’s trail at Skowhegan, a gritty mill town on Route 2 in central Maine. After a relatively easy upriver trip on the Kennebec, Arnold’s little army faced its first major obstacle: a 100-foot-high wall of cliffs, rapids, and falls. Their formidability is still plainly evident from the vantage point of Coburn Park just east of downtown, where you can see the island Arnold camped on and the steep terraces up and over which his men had to shoulder their bateaux up and over. Behind the Empire Grill downtown is the Skowhegan Watching Place, a narrow footbridge that takes you out over the river and gives an even more vivid sensation of what the army was up against.

These Skowhegan falls turned out to be just the beginning of Arnold’s month-long ordeal. The supply of food began to run out as the soldiers slogged through Great Carrying Place, a shortcut of ponds and bogs that led westward from the Kennebec to the Dead River; game was scarce, and by the time they reached Canada, the men were reduced to eating their leather moccasins. An unusually late New England hurricane struck while they were on the Dead, turning that placid stream into a raging torrent. The hurricane was followed by a blizzard, and a third of Arnold’s men under Col. Roger Enos turned back.

Arnold, who always believed in leading from the front, found the strength of soul to rise above all of this. There had been “a thousand difficulties I never apprehended,” he wrote in his report to Washington; one of his officers called him a “man of invincible courage; ever serene, he defies the greatest danger—you will find him ever the intrepid hero.” He was, more than one of the numerous diarists on the expedition wrote, “beloved by his soldiers.”

The enormous difficulty of this terrain—the wall-like mountains, the maze of rivers, the tenacious understory of briars and vines—remains obvious today. The route that mostly closely approximates his march leads from Skowhegan west to Norridgewock, then northwesterly along Route 16 to North Anson, North New Portland, and then Stratton and Eustis, near the notorious Height of Land, the mountain hump that tilts the watersheds toward Quebec. The Appalachian Trail crosses the highway near Mount Bigelow (named after one of Arnold’s officers), and it’s worth taking a half-hour’s hike just to get an appreciation of what marching through this forest must have been like. (Even as late as the 1930s local woodsmen could tell which way the army had gone by the line of hardwoods that sprang up after Arnold’s axmen had hewn down the original spruce.)

This is a lonely country still, especially on the Height of Land, where Route 16 climbs along Chain of Ponds, where starvation began looming as a very real possibility for the entire force. Driving it on a beautiful mid-July day, we only came across one other person, the proprietor of a small campground on the penultimate of the ponds.

“Yep, came through here all right,” the man said when I asked him about Arnold. He pointed to the flinty shore of the pond. “Why’d he go bad like that anyway?”

I shrugged and gave him the shortest explanation: “Married the wrong person.”

He nodded. “That happens. Well, the next pond you’ll see up the road is Arnold Pond, and after that they had to put their boats on their shoulders and carry them four miles. Heavy boats—wore the skin off down to the bone.”

It is important to try to understand what was in Arnold’s heart as he rode back and forth, forbidden to join the battle.

Surely this is the only corner of the world where Arnold is still remembered as a hero. The gas station in Stratton is called the Arnold Trail Service Station; there’s Arnold Pond near where Maine tips over into Canada, then, once you cross the border, the Rivière Arnold, which runs under Highway 161. My wife and I were delighted to find not one motel but two named after him in Quebec: the simple Motel Arnold in St. Augustin de Woburn, and the more upscale Auberge Benedict Arnold in Ville de St. Georges de Beauce on Highway 173 (the Route de President Kennedy, if one is speaking of heroes). Beauce was, in 1775, the first inhabited town on the Chaudière River and near the place where Arnold, racing ahead of his men, bought the cattle that saved them from starvation.

The Chaudière, which leads 100 miles to Quebec City, was so rapid from all the rain that it swamped most of Arnold’s boats, nearly drowning Daniel Morgan at the falls in St. Martin. Still, it was a picnic compared with what they had faced in Maine, and soon the army was in Quebec proper, waiting for Montgomery’s forces to join them from Montreal. An assault was planned for the first snowy night, which turned out to be December 31, 1775. Arnold, leading his men through the narrow streets of the Old Town below the cliffs of the fortress, was wounded in the leg, while Montgomery died leading the other fork of the pincers. With Dan Morgan captured, the leaderless men had no choice save surrender or retreat.

The street where Arnold was wounded, Rue Sault-au-Matelot in le Vieux-Québec, is still there today and gives you a good idea of what a formidable barrier his men had to storm. Three historical markers testify not to Arnold’s heroism but to that of the defending troops led by Sir Guy Carleton—markers that not one in a thousand of the tourist passersby give a second glimpse, though had Arnold not been wounded at the critical moment, it’s entirely conceivable that Quebec City would now be the capital of an American state.

Arnold’s adventures in Canada weren’t over yet. His little army kept up a brave “siege,” but once spring came, a British fleet arrived from England and set in motion a semiprecipitous American retreat south along the St. Lawrence to Montreal, then, via the Richelieu, to Lake Champlain. Typically, Arnold made sure he was the very last American to quit Canada, shooting his horse a few minutes before the British arrived, then hopping the last boat to leave St. John.

If you drive south from Montreal to St. Jean-sur-Richelieu and pick up Route 133 until it crosses into Vermont and becomes I-89, you’ll begin to understand why this corridor was strategically vital. To your west rise the high peaks of the Adirondacks; to the east, the barrier of the Green Mountains. The only way between them is the great open corridor of Lake Champlain.

This was the route that the retreating Arnold, now with an army under Carleton hot on his heels, had to find a way to block. Naval command of the lake was going to be imperative; Arnold, who had once sailed his own ships in the West Indies trade, proved just the man to hastily improvise a fleet. To see the kind of warship he managed to build, we stopped at the excellent Lake Champlain Maritime Museum at Basin Harbor seven miles west of Vergennes, Vermont. Anchored in a cove there, looking shipshape enough to stop Carleton should he ever come again, is the Philadelphia II, a 54-foot-long working replica of one of Arnold’s ships. (The original, dredged from the lake bottom, is now owned by the Smithsonian.)

The place where Arnold’s makeshift fleet eventually fought the stronger navy assembled by the British on October 11, 1776 (you can imagine the vivid autumnal foliage on the shore, the blinding blueness of the water), is Valcour Island, a short distance south of Plattsburgh on the New York side of the water. Ausable Point Campground off Route 9 gives a perfect view of this still wild, undeveloped island; walk along the campground’s beach, face the northeast, and you’re looking at the bay where Arnold anchored his ships, awaiting the attack by Carleton’s fleet sailing down the broad reach to your right.

Valcour Island was a brutal eight-hour-long mutual pounding, capped by one of Arnold’s most audacious enterprises: He escaped certain destruction by slipping his badly damaged fleet away under the noses of the British during the night, passing very close to the spot you’re standing on. Carleton, badly stung, lost all heart for his invasion and withdrew to Canada, giving the American forces enough breathing space to re-group. The great naval historian Alfred Thayer Mahan summed it up best: “Save for Arnold’s flotilla, the British would have settled the business. The little American navy was wiped out, but never had any force, big or small, lived to better purpose.”

Lake Champlain has a number of other sites associated with Arnold. Ferris Bay, near Panton, Vermont, is where, after a two-day chase, he set ablaze his ship Congress and got his men ashore one step ahead of the pursuing British. Across the lake in New York, Crown Point, with the original fortifications still visible, is one of the strategic chokepoints on Champlain that Arnold relied on to stop the British; the other, 13 miles south on Route 22, is Fort Ticonderoga, with its deservedly famous restoration.

But for us the place where Arnold’s spirit seems to live most vividly is Whitehall, New York, on the southernmost point of the lake, where it’s hardly wider than a sluggish river. In 1776 this was called Skenesboro after its Tory proprietor. Arnold built his fleet here, before sailing it up to Valcour Island, bringing shipwrights and carpenters from the coast to assemble the “gundalows” and “row galleys” he was counting on to stop the British.

He got his fleet built just in time, and Whitehall, this quiet, forgotten canal town many miles from the sea, has the distinction of being the birthplace of the American Navy, attested to by numerous historical markers spaced around the honorably shabby downtown harbor, markers that refer, almost apologetically, to “B. Arnold.”

An hour’s drive south of Whitehall, where Route 4 pinches in toward a narrow Hudson River, is the battlefield at Saratoga—for me, one of the most moving of American places. Here, in the autumn of 1777, were fought the two furious battles that stopped Gen. John Burgoyne’s invasion and proved vital in persuading France to ally itself with our cause. The most evocative spot in this remarkably unspoiled landscape may well be the gentle meadow that during the battle was known as the Breymann Redoubt, for the Hessian commander whose troops faced a furious American charge late on the decisive day of October 7.

At a corner of the meadow, shaded by trees and not obvious at first, is one of the strangest battlefield monuments ever erected, a beautifully sculpted left leg, elegantly booted, standing by itself on what appears to be a cannon, beneath which a short inscription explains—and doesn’t explain—what it commemorates: “In memory of the most brilliant soldier of the Continental Army who was desperately wounded on this spot, … winning for his countrymen the Decisive Battle of the American Revolution and for himself the rank of Major General.”

Arnold had been far from idle since Valcour Island. He had been dispatched to the west to deal with the right side of the British pincers, turning it back at Fort Stanwix, and now here he was back at Saratoga, under the command of Horatio Gates. No two men ever hated each other more; it didn’t help that in the first of the two Saratoga battles, Freeman’s Farm on September 19, Arnold won most of the glory for himself (and how often Arnold fought in foliage season!). Now, as fighting broke out on October 7, Arnold had been effectively relieved of his command, forced to stand idle as a spectator while his best troops came up against stiff British resistance and the battle’s outcome seemed suddenly in doubt.

This is a key moment in Arnold’s life, and it’s important to try to understand what was in his heart as he rode back and forth on his charger, forbidden to take part in the battle yet compelled by a fury he was powerless to stop. The fury came from so many sources, so much hurt and so much courage, that it’s almost impossible for us to comprehend, but surely part of it was his overwhelming sense that this landscape, this corridor, this waterway was his . Hadn’t he won it for himself on the excruciating portage over the Height of Land, or on the dark snowy streets of Quebec, or on the brilliantly whitecapped water off Valcour Island? This was his land, to defend to the last drop of his being, his to win for his country, his, ultimately, to one day sell for good British gold.

Arnold finds it impossible to resist his own courage. He gathers up some men, leads the vital charge that wins the Breymann Redoubt for the Americans, seals the victory, and, just as he crashes into the redoubt, is shot in the same leg that was wounded at Quebec.

Historians for years have always insisted that it would have been better for Arnold’s reputation if he had been killed at the peak of his glory in Saratoga, yet perhaps they miss the point. In a very real sense he was killed at Saratoga: the good Arnold, the one that for three brilliant years courageously overrode all his demons. Almost certainly Arnold sensed this himself.

Henry Dearborn rushes up to him, asks where he’s been shot. “In the leg,” Arnold tells him, then, in what is surely one of the saddest lines from American history, adds, “I wish it had been my heart.”

An Arnold Chronology To Plan A Trip


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