Tales from the rowdy route of mostly whiskey trade that ran from Fort Benton, Montana Territory, to Canada’s North-West Territories.
The colorfully named Whoop-Up Trail was not nearly as significant as the Santa Fe Trail far to the south and is little remembered today, but this spirituous route of commerce in the Old West certainly made its mark, for better or worse, on the American Northwest and Canada. The trail sprang up during the latter half of the 19th century, when western Canada was a vast, wild region populated mainly by nomadic, buffalo-hunting First Nations tribes and a scattering of trappers and traders. For nearly two centuries the dominant economic power in the region then known as the North-West Territories—which included present-day Alberta, Saskatchewan and parts of Manitoba, Ontario and Quebec—was the legendary Hudson’s Bay Co., one of the most successful mercantile enterprises in history.
Hudson’s Bay was incorporated in 1670 when King Charles II of England granted his cousin Prince Rupert of the Rhine and other investors a royal charter to trade in North America. Called Rupert’s Land, the grant was huge, at one time encompassing all of present-day Manitoba, most of Saskatchewan, southern Alberta and the northern parts of Ontario and Quebec, as well as slices of Minnesota, the Dakotas and Montana. At 1.5 million square miles it was nearly twice as large as the Louisiana Purchase.
In 1821, in response to an increasingly violent trade war in the region, the British government forced a merger between HBC and the North West Co., its leading competitor, essentially dissolving the latter while giving the former a monopoly in the region. During the 1830s HBC pressed south into the Missouri and Columbia rivers territory. Simultaneously, in the feverish race for furs, John Jacob Astor’s powerful American Fur Co. made its own inroads north into the Saskatchewan River drainage system.
During the early years of the fur trade Hudson’s Bay and American Fur battled for control of the region. By the mid- 19th century, however, HBC’s influence was on the wane. In 1870 the company surrendered its charter for Rupert’s Land to the British Crown, receiving 300,000 pounds in compensation, a transaction that virtually overnight transformed Canada into a vast dominion of Great Britain. It also created a trading void soon filled by opportunistic free traders from both Canada and the United States.
Recognizing the profit to be made from liquor traffic with First Nations tribes, those traders carved out a route that soon garnered the name Whoop-Up Trail. The origin of its name is uncertain, but the expression “whoop it up” had long been in common use, and bullwhackers reportedly shouted, “Whoop it up!” when they wanted their oxen to move faster. Others insist the trail name originated with one particular trader, who, when asked how things were going up north, replied memorably in fractured English, “Oh, we’re just whoopen on ’em up.” Regardless, the Whoop-Up Trail soon evolved into a mighty channel of overland commerce. It may very well have been the wildest avenue of Western entrepreneurial activity on either side of the border.
The free traders, the economic force that made the Whoop-Up Trail so profitable, carried a wide range of goods—tobacco, salt, sugar, flour, tea, axes, knives, blankets—but whiskey was far and away the most profitable trade item. Seldom did they trade in good whiskey, instead developing their own special formulas to trade for hides and pelts. The typical fiery mixture began with a base of whiskey, to which was added tobacco, ginger, red pepper and, on occasion, molasses and red ink for color. It was rotgut of the worst sort and at times must have seemed bottled straight from a bull wallow.
The resulting alcohol addiction played a role in diminishing the once powerful Blackfoot Indians (as they are known in Canada; usually styled Blackfeet, singular or plural, in the United States) into a tribe that was only a shadow of its former self. Although the peak period of the whiskey traffic lasted only about five years (1869–74), they were tumultuous years marked by a vigorous trade in whiskey, furs, firearms and ammunition. While the various tribes represented a customer base for traders, they could also on occasion be one’s deadly enemy, and by the 1870s many of the Indians were well armed with modern repeating firearms, thus increasing the risk of doing business, particularly illicit trade, in the region.
In addition to the whiskey traffic, the Whoop-Up Trail also carried thousands of tons of freight to government posts in western Canada. Between 1874 and 1885 the trail handled one-third of all the freight that passed through Fort Benton, Montana Territory, bound for the hinterland north of the international border. Traffic along the trail varied from travelers on foot and horseback to mule trains and trade wagons.
Within 100 miles of the border, Fort Benton was the hub for northbound traffic along the Whoop-Up Trail. Founded in 1847 by brothers Auguste and Pierre Chouteau, among the foremost of America’s fur trading entrepreneurs, the Upper Missouri River post quickly became an economic driver in the region. There was no more colorful community in the West than bustling Fort Benton, which soon claimed the moniker “Chicago of the Plains.” With the discovery of gold in the early 1860s in what soon became Montana Territory, the fort quickly became the terminus for steamboat traffic that carried prospectors, opportunists and emigrants bound for the land of quick wealth. Although by the mid-19th century the boom days of the trade in beaver furs were over, a ready market for buffalo hides and wolf pelts had developed to fill the economic gap. Indeed, by the mid-1870s brokers such as Thomas C. Power were shipping an estimated 100,000 buffalo hides and wolf pelts through Fort Benton annually. That business, combined with the emigrant traffic bound for Montana’s gold camps, ensured the continuation of Fort Benton’s spirited lifestyle. There was virtually no law of any kind, civil or moral, one visitor recalled. One historian termed the uninhibited inland port the “Sagebrush Sodom.”
From Fort Benton the Whoop-Up Trail snaked its way north along the banks of the Teton River, entering Canada near the Sweet Grass Hills. North of the border, after crossing the Milk River, the trail split into three routes—the eastern branch veering to the north end of present-day Lethbridge, Alberta; the central route heading to Fort Whoop-Up (originally Fort Hamilton), south of Lethbridge; and the westernmost course continuing on to Fort Macleod (built in 1874).
Fort Whoop-Up, a seven-day ride from Fort Benton, was easily the best known and certainly the most colorful of the whiskey trading outposts that pocked the Whoop-Up Trail, though other posts bore equally memorable names, such as Forts Slide-Out, Stand-Off and Robbers’ Roost. Although it was customary to refer to these trading posts as “forts,” they usually comprised little more than a rough log cabin, which either the traders themselves or Indians often burned down at the end of each season.
Fort Whoop-Up was the brainchild of Fort Benson– based traders John Jerome Healy and Alfred B. Hamilton. In 1869 the partners built a crude trading post, dubbed Fort Hamilton, at the confluence of the St. Mary and Oldman rivers. When disaffected Indians burned that post, Healy and Hamilton hired former Hudson’s Bay carpenter William Shanks Gladstone to construct a sturdy rectangular post near the same spot. The new structure, which came to be known as Fort Whoop-Up, incorporated heavy timber walls and blockhouses mounted with cannon to guard the approaches. The partners received financial backing from Hamilton’s uncle Isaac Gilbert Baker, who in 1866 had opened a store in Fort Benton.
Fort Whoop-Up operated as a self-contained community. Healy was the self-styled law and order. After venturing west in 1858 as a member of the 2nd U.S. Dragoons, he soon set aside a soldiering career to prospect in the Montana gold camps and the broader region. Having little luck, he tried his hand at a variety of ways to turn a dollar—town-site promoter, farmer, hunter, Indian fighter. In 1877, following his successful stint as post trader at Fort Whoop-Up, he was appointed sheriff of Chouteau County and soon became anathema to horse thieves.
During those lively early years any itinerant adventurer passing along the Whoop-Up Trail might enjoy the companionship of freighters and bear witness to the snap and pop of bullwhips, or perhaps trade tobacco for safe passage from a roving party of Blackfoot. By 1874, depending on the nature of one’s business, said traveler might also enjoy the company of the recently arrived, scarlet-clad North-West Mounted Police.
When the Mounties took up their station that summer, they soon focused their attention on the free traders, who had a mixed reputation in the region. Some saw them simply as innovative businessmen who provided a useful service to the Blackfoot, Bloods, Crees and other tribes. Missionaries, government officials and military commanders saw them as a destructive force. Healy, for one, argued that traders taught the Indians to behave and made the country safe for travel. Generally speaking, the Mounties found the traders to be a decent if rowdy bunch, mostly young men, many of whom were recently discharged veterans, Yankee and Confederate.
Wolfers—hunters who tracked and culled wolves for their pelts—were less welcome. Following on the heels of the traders, they also operated out of Fort Benton and plied the Whoop-Up Trail into the North-West Territories. Wolf pelts were much in demand, and American wolfers could turn a handsome profit. Between 1870 and ’74 they ran Fort Spitzee (a corruption of a Blackfoot word for “high”), an illicit trading post near the High River some 100 miles northwest of Fort Whoop-Up.
Traders and Indians generally loathed the wolfers, who lived like their prey and whose indiscriminate hunting methods relied on strychnine rather than guns or traps (bullet holes and leg wounds devalued the pelts). Lacing the organs of a buffalo with the poison, they baited hungry wolves to feast on the meat, then returned later to skin their carcasses. During the cold winter months, when game was often scarce, the scent of buffalo meat drew prey like a magnet. Problem was, the bait also drew domesticated dogs, costing the Indians many valuable animals. In the 1880s Montana, prompted by ranchers fed up with livestock losses, offered a bounty for dead wolves, which made hunting the animals even more profitable and led to even more brutal methods. Wolfers developed a favored tactic called “denning,” in which they would locate a den, kill the female and then slaughter her cubs to collect the bounty.
Indians tended not to bother the traders, who represented a source of food, whiskey and weapons. But the hated wolfers, who operated in small groups of three or four, proved easier prey, and the Indians picked them off whenever they could.
Wolfers had their own ax to grind with traders for selling rifles and ammunition to Indians, thus putting their livelihood, not to mention their lives, at greater risk. They beseeched the traders to stop selling firearms to Indians, but the traders refused to give up the lucrative trade. Rebuffed, the wolfers organized a band of some 60 vigilante riders dubbed the Spitzee Cavalry. Its mission? Force the traders to suspend firearm sales to the Indians or drive them from the region. At Fort Whoop-Up, John Healy remained especially defiant and fired off a letter to the cavalry, telling them he would continue selling the Indians anything they wanted, asking them to leave his traders alone and suggesting they meet to discuss the issue. The Spitzee troopers rode down to Fort Whoop-Up to confront him. Angry rhetoric filled the air and threats abounded, but Healy defused the situation and convinced the wolfers the traders were there to stay. The grumbling wolfers finally departed, and the Spitzee Cavalry soon mustered out.
Increasing and often lurid accounts of lawlessness made it clear that if the dominion were to expand toward the setting sun, authorities must bring order to the West. The violence culminated in the 1874 Cypress Hills massacre, in which a group of wolfers and traders, seeking vengeance for the loss of stolen horses, attacked blameless Assiniboines, killing at least 20 and burning their village.
In fact, law and order was coming to the North West Territories. A year prior to the massacre the Canadian government had created the North-West Mounted Police. Renamed the Royal Northwest Mounted Police in 1904, the force merged with the Dominion Police in 1920 to become the Royal Canadian Mounted Police still operating today.
It is doubtful whether any single law enforcement agency has ever been assigned so vast a territory. Until 1870 Canada comprised only four provinces. But in 1870 the government created the provinces of Manitoba and British Columbia, and
virtually everything west of present-day Manitoba became the North-West Territories, including Alberta and Saskatchewan, which were not designated provinces until 1905. The 1870s International Boundary Survey coincided with the arrival of the North-West Mounted Police in the region, but most of the Canadian West remained terra incognita.
The North-West Mounted Police consisted of six divisions of 50 men each, under the overall command of a commis sioner. Leading each division were a superintendent, an inspector and two sub-inspectors. Men signed up for threeyear terms, for which they would be paid 50 cents a day. The position of commissioner was assigned to Lt. Col. George Arthur French, a British artillery officer. It took nearly a year for French to get his new organization in shape to meet its new responsibilities. Finally, on July 8, 1874, the Mounties in their shiny new uniforms marched out of Fort Dufferin, Manitoba, bound for the North-West Territories. That October they established Fort Macleod, and in 1875 they built Fort Brisebois (renamed Fort Calgary in 1876).
Although ending the whiskey trade was a key reason for the creation of the force and construction of the forts, the Mounties also had to deal with boundary disputes, smuggling and the possibility of a cross-border Fenian invasion. The Fenian Brotherhood, founded in the United States in 1858, was an offshoot organization of Irishmen who sought independence from England and figured to achieve that goal by invading and holding Canada hostage. The planned invasion never happened, but it stood as a threat the Mounties had to consider. They were also responsible for safe guarding the welfare of the First Nations.
The arrival of the NWMP force quickly sounded a death knell for the illicit whiskey traders, but there remained a need among the Blackfoot and other Indians for flour, sugar and pemmican. Thus, the Mounties ushered in a new era of commerce on the Whoop-Up Trail. Many present-day American tourists driving north to visit the beautiful communities of Banff and Lake Louise in the Canadian Rockies follow the general course of the Whoop-Up Trail. Most have little notion of the history that surrounds them as they pass through a region of seemingly endless grasslands and wheat fields. With a little imagination, though, one can visualize the lumbering freight wagons and hear the drivers’ yells and cracking whips as they made their way north toward one of the trading posts along the Whoop-Up Trail.
Colorado author Jerry Keenan has written for Wild West since 1988. For further reading: Whoop-Up Country, by Paul F. Sharp; A Double Duty, by Jim Wallace; and Healy’s West: The Life and Times of John J. Healy, by Gordon E. Tolton
Originally published in the April 2015 issue of Wild West. To subscribe, click here.
