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One of the toughest sections along the historic Bozeman Trail existed in a portion of the 10 to 12 miles between Pryor Creek and the present-day Billings Motorcycle Club on the banks of the Yellowstone River.

“So we start this AM & travel over some of the roughest hills I ever saw often we are on a narrow ridge just wide enough for a wagon & again pulling up a steep acclivity by means of ropes & letting down again by the same means,” wrote Theodore A. Bailey in his 1866 diary of his trip.

Such details are revealed in a collection of Bozeman Trail diaries included in historian Susan Badger Doyle’s two books, “Bound for Montana, Diaries from the Bozeman Trail” and “Journeys to the Land of Gold, Emigrant Diaries from the Bozeman Trail, 1863-1866.”

“The Bozeman Trail was one of these overland gold rush trails,” Doyle writes.” A shortcut from the Platte River Road to the Montana goldfields, it was relatively short in length — less than five hundred miles; stunningly brief in existence — a mere four years from 1863 to 1866; and strikingly little used — only thirty-five hundred emigrants traveled over it. Yet the Bozeman Trail, opening in the midst of the Civil War and closing just prior to completion of the first transcontinental railroad in 1869, has the enduring distinction of being the last great overland emigrant trail in the American West.”

Diary entries

Despite being just south of Montana’s largest city, the South Hills section of the Bozeman Trail remains undeveloped within a swath of public and private lands. With the exception of buried natural gas and oil pipelines, much of the hills are still grazing land that probably look similar to what westbound travelers saw about 150 years ago. Certainly the hills are just as steep.

Ellen Gordon Fletcher, who had left a pampered life on a New York farm, wrote of the route to Billings on July 6, 1866: “We came to a very steep place about noon. The road had been over hills but we then came to some of the roughest wildest looking hills we have had to pass over.”

The diary entries contain little capitalization or punctuation as well as misspellings, yet they clearly spell out the struggles of the journey. They also describe the Billings area as rich in buffalo, good grass and timber.

“quite a valley along the river on the other side and as we came in sight of it from the top of the bluffs it was literally covered with buffalo as far as you could see also on the road to day they (buffalo) were if any odds thicker than ever and frequently ran so close to the train that the drivers could shoot them down as they walked beside their teams,” wrote C.M. Lee, a teamster, on Sept. 22, 1865.

First ORVers

The Bozeman Trail’s first entrance into what is now Yellowstone County occurred along an ill-defined route that likely made use of buffalo and American Indian trails. Each wagon train likely took a slightly different path.

The wagon train Bailey accompanied, perhaps poorly guided, went down Bitter Creek past what is now Pictograph Caves State Park to the Yellowstone River before having to turn around and backtrack, their route blocked by the steep cliffs and hills at the creek’s mouth. Yet all of the wagon trains that traveled toward what would become Billings eventually ended up in the same place: on the Billings Motorcycle Club’s grounds.

The pioneers and prospectors who took wagons up and down these same steep clay hills covered in sagebrush and grass that are now crisscrossed with motorcycle trails. So the wagons were the first off-road vehicles to make use of the area, joked Mike Penfold, a Billings resident who has studied the history and location of the Bozeman Trail.

The emigrants also dropped down to the Yellowstone River at the same place that Sgt. Nathaniel Pryor and three other men likely drove their remaining horses south across the waterway and through the hills during their 1806 journey en route to the Dakotas.

Tough going

For the emigrants to get through such rough country as Billings’ South Hills, they had to be creative. Sometimes they would dig a ditch into the dirt to lessen the angle for wagons across hillsides, Penfold explained.

They could also take the smaller wheels on the front of the wagon and put them both on the uphill side and the larger rear wheels on the downhill side of the wagon to lessen its leaning.

“They went up and down more than they went around,” Penfold said.

Going down steep hills, the emigrants would sometimes chain the wagon’s wheels — called a rough lock — and then let the oxen or mules drag the wagon downhill. On really steep sections, they would sometimes set a post or use a tree as a tie-off point to lower or pull up the wagons by a rope tied to the axle.

Lee’s diary contains a very detailed description of the troublesome drop from the South Hills into the Yellowstone River bottom.

“the descent from the bluffs to the river is very steep and dangerous at least two hundred feet I should judge the first half is not very steep then pass along a descending and sideling ridge barely wide enough for a road for a couple of hundred yards to the last descent which is at an angle of about 65 degrees and around a curve with only just room for the road before starting down this last hill we rough locked both hind wheels with log chains and went ahead trusting to Providence all got down safely”

Considering the difficulties of such travel, it’s amazing the emigrants made it at all. Some didn’t, dying from sickness or killed in accidents or in fights with Indians along the way. Davis Willson’s 1866 diary noted that, “In all the trains that have come up to the present time there have been 10 killed and 5 wounded. (Nathan) Floyd had his head cut off. How many have been killed who were in advance of us we do not know. The Capt of the post (Capt. Joseph L. Proctor) has had 33 killed reported to him.”

Short life

Although the Bozeman Trail was short lived, the route that came to the Yellowstone River near Billings had an even more brief life. In 1865, when the Army sent a road-building crew along the trail, they avoided the rugged South Hills.

By 1866, emigrants had abandoned the Billings route in favor of a road that traveled along Bad Pass north of Bighorn Canyon and followed the Clarks Fork of the Yellowstone River downstream to the Rock Creek Valley. The new route proved easier and meant that travelers didn’t have to struggle through the South Hills, move upstream to Blue Creek and climb the hills again before dropping down Duck Creek to reach the Clarks Fork River.

So the Bozeman Trail is not one distinct route. It was moved and realigned according to the wagon train leaders who were always searching for a better, easier, safer way. But for a short time, at least, some of those emigrants dropped down to the Yellowstone River just south of Billings.

For a student of history like Penfold, a chance to walk along the same hills in search of that likely route is a connection to the rugged past of our pioneer ancestors. Hiking the hills and scanning for a likely trail the emigrants may have taken, the possibilities seem to narrow yet still prove elusive.

“You’ve got to speculate a heck of a lot, but they wouldn’t have gone over there,” Penfold said pointing to the hills above Blue Creek, “or over here” he added, pointing toward Pictograph Caves. More likely, the emigrants came right over the hill on which he was standing.

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Montana Untamed Editor

Montana Untamed editor for the Billings Gazette.