JASMA

When most people hear the word “highwayman,” they picture a dashing
English rogue in a tricorn hat shouting “stand and deliver!” on some
foggy country road. But the United States had its own share of mounted
robbers and roadside killers, and many of them were far less romantic
and much more terrifying than the folk legends suggest.

Buried in county archives, old court records, and local folklore are
stories of American highwaymen who robbed mail coaches, ambushed
wagons, preyed on river traffic, and turned lonely inns and ferries
into death traps. These criminals were famous in their day, yet they’ve
largely vanished from mainstream history, overshadowed by better-known
outlaws like Jesse James or Billy the Kid.

This deep dive revisits ten lethal American highwaymen (and a few
murderous partners) that history largely left behind. From Revolutionary
War–era rebels to Old West stagecoach robbers, these are the forgotten
figures who turned early American roads into hunting grounds.

What Exactly Is a Highwayman?

In simple terms, a highwayman was a robber who targeted travelers on
public roads. In Britain, that usually meant a mounted bandit armed
with pistols and a flair for dramatic one-liners. In America, the
picture was messier. The country’s vast distances and rough frontier
meant “highwaymen” could be:

• Mounted robbers stopping stagecoaches or wagons on postal or trade routes
• River pirates attacking boats on major inland “highways” like the Ohio River
• Innkeepers and ferrymen who lured travelers into ambushes on key roads

Whether on horse, in a wagon, or working from a riverside cave,
highwaymen exploited the same basic problem: people had to move
goods and money along predictable routes, often with little or no
protection.

10 Forgotten American Highwaymen (and the Bloody Trails They Left)

10. The Doan Brothers: Quaker Sons Turned Revolutionary Roadmen

In the 1780s, eastern Pennsylvania discovered that even peaceful
Quaker country could produce dangerous outlaws. The Doan brothers
Moses, Aaron, Mahlon, Joseph, and Levi began as disgruntled
Loyalists furious that Patriot authorities had confiscated their
father’s land during the American Revolution. Their response was not
exactly a strongly worded letter.

Between 1781 and 1788, the Doan gang launched a spree of robberies,
jailbreaks, and shootouts across Bucks and neighboring counties.
Their most infamous score came in October 1781, when they robbed
the Bucks County treasury at Newtown, escaping with more than a
thousand pounds sterling that was never recovered. Local tax
collectors, riding with coin and paper receipts, quickly became
their favorite targets.

Authorities finally struck back. Moses Doan was tracked down and
killed, reportedly in a hail of gunfire. Levi and their cousin
Abraham were captured and hanged in Philadelphia as an example to
other Loyalist-leaning bandits. The remaining brothers fled
some likely to Canada or England leaving behind a legacy that
blurred the line between political resistance and hard-core violent
crime.

9. Ben Kuhl: The Bloody Palm Print in the Nevada Snow

Skip forward to December 5, 1916, and the Old West is essentially
over barbed wire is up, the frontier is “closed,” and cars are
starting to replace wagons. But one last lethal echo of the classic
stagecoach robbery still played out near Jarbidge, Nevada.

Mail driver Fred Searcy was ambushed on a snowy route as he drove
a small horse-drawn mail wagon. He was found shot in the head, and
about $4,000 in gold coins vanished. In the cold, silent canyon,
the killer left behind something much more incriminating than
spent cartridges: a bloody palm print on an envelope.

Suspicion fell on Ben Kuhl, a drifter with a record for theft and
trouble. Witness testimony pointed his way, but it was that bloody
palm print entered into evidence at trial that made history.
Kuhl became the first person in the United States convicted of
murder using palm-print evidence, a forensic milestone born from an
otherwise brutal roadside robbery. His death sentence was later
commuted to life in prison, and he eventually died a free but sick
man, far from the frozen mail route that sealed his fate.

8. Joseph Thompson Hare: The Highwayman Haunted by a White Horse

Joseph Thompson Hare’s life reads like a fever dream of the early
republic. Originating in Pennsylvania, Hare headed south toward New
Orleans in the 1790s, fell in with a trio of like-minded villains,
and began a career of ambushing peddlers and farmers on remote
routes. To make matters even more terrifying, the gang reportedly
smeared their faces with dark berries, creating a grotesque,
blood-like mask to frighten victims before robbing and sometimes
killing them.

The group drifted across the backroads of the young United States,
tangling with Native traders and Spanish authorities, occasionally
winding up in jail and somehow managing to slip back out. Eventually,
Hare started experiencing what he described as ghostly visions on the
trails including a mysterious “magnificent white horse” that
supposedly appeared to him in the woods.

One such vision delayed his escape long enough for a posse to catch
him. After several years in prison, Hare claimed to have reformed,
but he soon returned to crime. His final act was robbing a night mail
coach near Baltimore. This time there was no second chance: in 1818,
he was hanged before a crowd of hundreds, another early American
highwayman whose life ended at the gallows.

7. Michael “Captain Lightfoot” Martin: Last of the New England Highwaymen

Michael Martin, better known by his dramatic alias “Captain
Lightfoot,” started his outlaw career far from American soil.
Born in Ireland in the 1790s, Martin fell under the influence of a
mysterious road bandit who called himself “Captain Thunderbolt.”
Thunderbolt trained the quick-footed young man in the arts of
robbery, and together they robbed wealthy travelers across Ireland,
Scotland, and England supposedly avoiding the poor and women
in a twisted code of ethics.

Eventually Martin crossed the Atlantic and brought his talents to
New England, where he resumed robbing travelers on busy roads near
Boston and Salem. His daring, and occasionally theatrical behavior,
made him one of the last true “highwaymen” in that part of the
country.

His luck ran out after he robbed Major Bray, a Boston dignitary, and
Bray’s wife for a relatively paltry sum. Arrest, escape, and
recapture followed in rapid succession. In 1821, Martin was hanged
for highway robbery, making him widely remembered as the last person
executed in New England for that specific crime. His confession,
published later, helped cement the mythic image of “Captain
Lightfoot” as a glamorous criminal even if his real victims
probably felt otherwise.

6. James Ford: “Satan’s Ferryman” of the Ohio River

Few American criminals played a double game as successfully as James
Ford. Publicly, he was a pillar of frontier society in Kentucky and
southern Illinois: a justice of the peace, militia captain, land
owner, and operator of a strategically crucial ferry across the Ohio
River near the notorious Cave-in-Rock.

Privately, Ford was the mastermind of the Ford’s Ferry Gang, a
network of road and river bandits who preyed on travelers moving
through the region. Flatboats and wagons were quietly steered toward
danger; heavily loaded travelers might find themselves robbed, beaten,
or simply never seen again. His blend of civic respectability and
ruthless crime earned him the chilling nickname “Satan’s Ferryman.”

Rumors tied Ford to counterfeiters, slave kidnappers, and the
so-called “Reverse Underground Railroad,” in which free Black people
were abducted and sold into slavery in the Deep South. Eventually,
vigilantes had enough. In 1833, Ford was ambushed and killed near his
own ferry, likely by men who had once been part of his criminal
circle. The frontier had devoured one of its own.

5. Potts Inn: When Your “Cozy” Roadside Stay Is a Death Trap

Sometimes, the highwayman did not ride out to meet you you came
straight to him. In the early 19th century, travelers along the road
connected to Ford’s Ferry might stop at a rough little establishment
known as Potts Inn, run by Isaiah and Polly Potts in what is now
southern Illinois.

From the outside, the inn looked like a welcome break on a long,
muddy journey: food, drink, a bed, and a roof over your head. But
frontier lore suggests that some of those travelers never checked
out. Accounts describe the Pottses luring in guests, killing them,
and burying the bodies in shallow graves on or near the property.
Others may have been ambushed on the road leading to the inn itself.

One especially dark legend claims the couple even murdered their own
estranged son, Billy, without realizing who he was until it was too
late. Whether every detail of that story is true or not, the Potts Inn
has gone down in local history as a chilling example of how seemingly
respectable roadside businesses could be part of a larger web of
highway robbery and murder.

4. David “Robber” Lewis: The Robin Hood of Pennsylvania

David Lewis, often nicknamed “Robber Lewis,” earned a complicated
place in Pennsylvania folklore. Born near Carlisle around 1790, he
briefly served in the U.S. Army, deserted, and dodged the consequences
by slipping into a new profession: counterfeiting and robbery.

Operating across the hills and valleys of central Pennsylvania, Lewis
robbed wealthy travelers and wagons on key routes and reportedly stashed
loot in caves, some of which treasure hunters still obsess over today.
His hideouts, including spots like Doubling Gap, became part of local
legend. Stories claimed he sometimes shared money with the poor, fueling
the “Robin Hood” comparisons that still cling to his name.

Reality was harsher. Lewis spent time in and out of jail, survived
multiple escapes, and sustained serious injuries while fleeing
authorities. In the end, he died in custody around 1820, his wounds
infected and his romantic outlaw career over. The road rumors and
treasure tales outlived the man who inspired them.

3. Henry Plummer: Sheriff by Day, Highwayman by Night

Henry Plummer is one of those frontier figures whose true story is
still hotly debated but the legend that stuck is chilling. In the
1850s and early 1860s, Plummer bounced between roles as a miner,
lawman, and accused killer in California and the mountain West. He
eventually became sheriff of Bannack, Montana, just as gold strikes
turned that corner of the territory into a booming, dangerous zone.

According to many accounts, Plummer secretly ran a gang of road
agents known as “The Innocents.” While wearing the badge, he allegedly
fed them inside information on stagecoach routes and gold shipments,
and possibly used his position to shield them from accountability.
Miners and settlers traveling with gold dust or coin faced ambush and
murder along trails that Plummer himself was supposed to patrol.

Eventually, local vigilantes decided they were done waiting for
official justice. In 1864, a group of citizens hanged Plummer and
several alleged associates from a makeshift gallows. Whether he was
the mastermind the legends claim or only partially involved, his name
is now permanently tied to the shadowy overlap between frontier law
enforcement and organized road robbery.

2. Samuel Mason: River Pirate of Cave-in-Rock

If early American rivers were the interstate highways of their day,
Samuel Mason was one of their deadliest predators. A former militia
officer and sometime landowner, Mason reinvented himself as a river
pirate in the late 18th century, using the natural fortress of
Cave-in-Rock on the Ohio River as his criminal headquarters.

Mason’s gang reportedly lured flatboats and keelboats to shore with
deceptive signs like “Liquor Vault and House of Entertainment” and
by staging fake distress scenes with accomplices on the riverbank.
Once travelers came ashore to rest, trade, or rescue the “stranded,”
Mason’s men robbed and often murdered them, dumping weighted bodies
into the river so they would sink.

Eventually, authorities caught up with him. Captured and handed over
to Spanish officials, Mason attempted an escape while being transported
but was killed in the process. In a grisly twist, one of his own
associates later delivered Mason’s severed head to claim a reward
only to be recognized as a criminal himself and executed. Karma, as
they say, can be extremely literal.

1. The Harpe Brothers: America’s First Serial Killers

Of all the violent figures linked to early American roads and trails,
the Harpe brothers Micajah (“Big Harpe”) and Wiley (“Little Harpe”)
may be the most terrifying. Active in the 1790s in Kentucky,
Tennessee, and surrounding frontier regions, they didn’t fit the
typical highwayman mold. They were less interested in profit than
in killing for its own sake.

Traveling with their wives and children, the Harpes murdered settlers,
travelers, and entire families with shocking cruelty. They are
associated with the Cave-in-Rock region as well, where their violence
reportedly disturbed even hardened river pirates. Estimates of their
victim count range into the dozens, leading some historians to call
them America’s first documented serial killers.

Big Harpe’s end came when a posse tracked him down; he was shot,
fatally wounded, and then decapitated, his head placed on a tree or
post as a warning. Little Harpe escaped, briefly reappeared with
Samuel Mason’s gang, and ultimately met the same fate as many
criminals of his era: execution by hanging. Their story stands as a
stark reminder that not all outlaws were lovable rogues some were
simply predators.

Why History Forgot These Highwaymen

So why aren’t these names as famous as Jesse James or the Dalton
Gang? Several factors pushed these highwaymen to the margins of
popular memory:

• Bad timing: Many of them operated before the
  “classic” Wild West era that Hollywood glamorized, so they missed
  the cultural spotlight.
• Remote victims: They targeted isolated farmers,
  boatmen, and small-town travelers, not banks or trains with
  dramatic newspaper-ready headlines.
• Moral complexity: Some, like James Ford and Henry
  Plummer, wore both criminal and civic hats. Their communities were
  often reluctant to fully confront how corrupt their “respectable”
  leaders had been.
• No good PR team: Legends stick when ballads,
  dime novels, and later films keep them alive. Many of these
  stories survived mostly in local histories and dusty court records.

Yet together, these forgotten figures show just how dangerous travel
could be in early America and how thin the line was between safety
and sudden violence on lonely roads and rivers.

Modern Road-Trip Reflections on Old-Time Highwaymen

It’s one thing to read about these highwaymen sitting at a desk; it’s
another to imagine driving through their old hunting grounds with the
GPS politely telling you to “turn left in 500 feet.” If you’ve ever
taken a long American road trip, you’ve probably passed more history
than the roadside markers let on.

Picture yourself driving across rural Pennsylvania at dusk. The
highway dips into a wooded valley, cell service blinks in and out, and
a green sign lists a tiny town you’ve never heard of. Somewhere off to
the side, a historical marker might quietly mention a treasury robbery,
a jailbreak, or an early 19th-century hanging. That’s Doan or David
Lewis country places where travelers once rode with coins in their
saddlebags and more than a few nervous glances over their shoulders.

Head west and the landscape opens up into Nevada desert. Near Jarbidge,
the modern road feels endless, the sky big, the towns small and far
apart. It’s beautiful, but you quickly understand why a lonely mail
wagon in 1916 was such an easy target. There’s nowhere to hide, but
also nowhere to run. Today, the worst you’re likely to meet is a flat
tire or a dead battery but the silence still feels heavy in a way
that connects you to Ben Kuhl’s doomed victim more than a century ago.

Down along the Ohio River, it’s a different vibe: soft hills, water
gleaming through trees, and the occasional ferry or riverside town.
Families fish from the bank; people walk dogs on paths that would
have been muddy tracks two centuries earlier. It’s scenic and
peaceful, yet beneath that calm lies a darker story Ford’s Ferry,
Cave-in-Rock, and a network of river pirates and land highwaymen who
turned this corridor into one of the most perilous routes in the
country. Stand on a bluff there at sunset and it’s not hard to imagine
a lantern signal flashing on the opposite bank, calling in a boat that
would never arrive at its supposed destination.

Even our modern travel habits echo older anxieties. We worry about
sketchy gas stations in the middle of nowhere, about taking the wrong
exit at night, about who else is staying at that too-cheap motel off
the highway. The risks may look different now credit card skimmers
instead of pistol-waving riders but the basic vulnerability of the
traveler hasn’t changed all that much. You’re away from home, carrying
valuables, and relying on strangers and infrastructure you don’t
control.

Thinking about these forgotten highwaymen while you travel doesn’t
mean you have to turn every road trip into a true-crime podcast in
your head. But it does add a layer of perspective. Those smooth,
well-marked highways sit on top of centuries of trial and error,
violence and reform: better law enforcement, improved communication,
and communities that finally decided they were tired of being hunted.

If you’re into “dark tourism,” you can actually visit some of these
places old ferry sites, inn locations, historic caves, and small
museums that preserve artifacts and stories from the era of American
highwaymen. The key is to approach them with respect. These aren’t
just cool villains from an action movie; they’re people who left real
victims and grieving families behind.

In a way, remembering these lesser-known criminals is a strange form
of gratitude. The next time you breeze down an interstate at 70 miles
an hour, with roadside rest areas, emergency call boxes, and a phone
that can summon help in seconds, you’re living in a world built
precisely so you don’t have to worry about becoming the next name in
some grim county history under the heading “robbed and murdered on
the highway.”

Final Thoughts: The Dark Side of the Open Road

The ten highwaymen and outlaw gangs in this list were not charming
rogues or misunderstood heroes. They were opportunists, predators,
and, in some cases, outright sadists who exploited the vulnerabilities
of a young, expanding nation. Yet their stories are still worth
remembering not to romanticize them, but to understand how fragile
safety and order once were on America’s roads and rivers.

Today, most of us fear traffic jams more than highway robbers, and
that’s a good sign of progress. But beneath every smooth stretch of
asphalt lies a rougher past: muddy tracks, isolated ferries, dangerous
taverns, and the ever-present possibility that someone like James Ford
or Samuel Mason was waiting just around the bend.