The Whoop-Up Trail

By editor

Dutton, Teton County, Montana

In the latter half of the nineteenth century, as the restless currents of American expansion surged westward and the vast, untamed plains lay stretched beneath an endless sky, a singular artery of commerce and conflict emerged--known to those who traversed it as the Whoop-Up Trail. This route, extending some two hundred miles from Fort Benton, Montana, to the confluence of the Belly and St. Mary rivers in what is now southern Alberta, Canada, shaped a chapter of frontier history marked by ambition, avarice, and the complex interplay of cultures amid the waning days of the buffalo hunt.

From the year 1869 until 1885, this trail served as the conduit through which supplies and trade goods, having journeyed northward along the Missouri River from the distant city of St. Louis, were transferred at Fort Benton from the paddle-wheeled steamboats to freight wagons. These wagons then bore their burdens across the rugged expanses of the northern plains, delivering goods to the farthest reaches of the Canadian frontier. The establishment of this trail was the enterprise of two enterprising men of the American West, John J. Healy and Alfred B. Hamilton, who in the year 1869 constructed a trading post at the junction of the Belly and St. Mary rivers--an outpost they christened Fort Whoop-Up.

Fort Whoop-Up, the first of a series of establishments colloquially termed "whiskey forts," rapidly became notorious along the frontier. Here, American traders engaged in the exchange of tobacco, sugar, knives, beads, and, most perniciously, whiskey of dubious quality--referred to then as “rot-gut”--with the Blackfeet Nation. In return, they received buffalo robes and wolf pelts, commodities of great value in eastern markets. The commerce was undeniably profitable, and the fortunes amassed by these traders were substantial. Yet, the profits came at a grievous cost to the Blackfeet, whose social fabric and health were grievously undermined by the introduction of ardent spirits and the destabilizing effects of this commerce.

The origin of the trail’s curious appellation, "Whoop-Up," remains shrouded in uncertainty, though one anecdote, preserved by a venerable frontiersman, offers a glimpse of the vernacular life upon these plains. When Johnny LaMotte, a trader known among the frontier community, returned to Fort Benton from his dealings across the border, he was queried about the state of business. His reply, delivered with the frankness of a man accustomed to the rough realities of frontier trade, was, “Aw, they’re just whooping ’er up!” Thus, the phrase entered the lexicon, capturing the raucous spirit of the trade and the revelry that often accompanied it.

The existence and operations of these whiskey forts soon drew the attention and ire of authorities on both sides of the international boundary. The Canadian government, confronted with the deleterious effects of the whiskey trade upon its Indigenous populations and the disorder sown along its frontier, took decisive action. In 1874, the Royal Canadian Mounted Police--newly formed and imbued with the solemn duty of law enforcement in the western territories--were dispatched to the region. Their mission was to expel the American whiskey traders from Canadian soil and assert the sovereignty of the Canadian government over its northern frontier. The RCMP’s intervention was met with resistance, yet it signified a turning point in the regulation of cross-border commerce and the assertion of order amid the frontier’s lawlessness.

The removal of the whiskey traders from Canadian territory did not, however, spell the end of the economic opportunities presented by the Whoop-Up Trail. Fort Benton merchants and traders, recognizing the enduring demand for supplies by the Mounted Police and the settlers who followed, redirected their commerce to provision the new RCMP posts established throughout southern Alberta. Thus, the trail remained a vital artery of trade, albeit now under the auspices of legitimate commerce, rather than illicit dealings.

Yet, the very forces that had propelled the Whoop-Up Trail into prominence would soon render it obsolete. The completion of the Canadian Pacific Railway in 1883 marked a transformative moment in the history of the northern plains. This iron road, stretching across the breadth of the Canadian West, provided a swifter and more reliable means of transporting goods and settlers alike. In the wake of the railway’s arrival, the once-bustling freight wagons of the Whoop-Up Trail ceased their journeys, and the trail itself fell into disuse, fading into memory as the frontier was reshaped by the inexorable advance of civilization.

The story of the Whoop-Up Trail is thus one of contrasts. It chronicles the ambitions of men who sought fortune amid a vast and challenging landscape, the cultural exchanges--both beneficial and destructive--between traders and Indigenous peoples, and the assertion of national authority over a contested borderland. The trail’s history also presages later episodes of cross-border trade, including the rum-running routes of the Prohibition era, when the movement of illicit goods once again threaded through these plains, echoing the patterns established decades earlier.

In reflecting upon this episode, one is reminded of the words of the historian and statesman Lord Acton, who observed, “Power tends to corrupt, and absolute power corrupts absolutely.” While not an exact parallel, the fortunes gained by the whiskey traders at Fort Whoop-Up reveal how unchecked commerce and the absence of regulation on the frontier could yield both wealth and ruin--particularly for the Indigenous peoples whose lives and lands were irrevocably altered.

The Whoop-Up Trail, then, occupies a singular place in the chronicles of the American West and Canadian Northwest. It embodies a moment when the forces of empire, commerce, and culture converged upon the plains, leaving an indelible mark upon the landscape and its peoples. Though the wagons no longer traverse its path, the trail’s history remains a vital chapter in understanding the complexities of frontier life and the relentless transformations wrought by the march of progress.

See also

• The Whoop-Up Trail at Dutton, Teton County
• An Island on the Plains at Fort Benton, Chouteau County
• Tale of Two Treaties at Fort Benton, Chouteau County