South Dakota’s initial passageway of travel was the Missouri River.  Later, the wagon road followed the establishment of military forts and settlers moving into the territory.  Some of the first roads established in South Dakota were along the Missouri River.

In general, the development of roads across the prairie followed the lines of the old and well-traveled buffalo and Indian trails.  They became roads used by the early settlers.  Some of these routes would later become the Township, County, State, and Federal roads used in South Dakota today.

One of the earliest historic journeys across Gregory County was that of Father Pierre DeSmet.  He left St. Louis in the spring of 1848 by boat and traveled to the mouth of the Platte in Nebraska.  From there he proceeded overland on horseback for twenty-five days to the mouth of the Niobrara.  During that time he was almost driven to distraction by mosquitoes, gnats, and horseflies.

From the mouth of the Niobrara he traveled across Gregory County to Fort Pierre.  His trail is uncertain; however, it is known that he departed the county in the northwest corner.  He probably followed one of the trails natives had been using for decades.

After the Civil War, Dakota Territory was transformed into an area with roads which were planned and constructed by the army.  With an established network of forts in the Dakotas and Montana, it was necessary for roads to be constructed and a reliable transportation system established.  Men and materials were continually being moved between the supply depots and the forts.

Fort Randall became a major hub for the distribution of supplies by freighters.  It had become the supply depot for the forts farther up the river and those west on the frontier.

The army had its own means of transport; however, it preferred to employ civilians who were under contract to move men and supplies.  Freight wagons, stage coaches, riverboats, and where available the railroad were all utilized.

There was a great contrast in the various wagon and stage coach roads.  They varied from the Indian trail on which few improvements had been made to those which showed the ruts from many heavy wagons.  A heavily load wagon was able to cover fifteen to twenty miles in a good days travel.  The road continued to serve the farmers and ranchers after the forts were abandoned.

The Deadwood-Yankton Freight Road was a major route to transport freight and supplies between 1865 and 1890.  Freight would come up to Fort Randall from Yankton by boat or wagon.  From Fort Randall the wagons crossed the southern part of Gregory and Tripp counties on their way to Deadwood.

About 1870, the Whetstone Landing located at Whetstone Agency on the Missouri River was established.  Substantial buildings were erected at the mouth of Whetstone Creek where the steamboats deposited most of the supplies for the Brule and Oglala tribes.

Harney City was located opposite the Whetstone Landing and was notorious for a time as the “liveliest settlement in the territory.”  This was one of the main reasons why Chief Spotted Tail did not want to remain on the Missouri River.

The Rosebud Agency, built in 1878, was as complete as any of the numerous agencies in Dakota.  Its location and actual improvement was a decided victory for Spotted Tail.

The Landing Creek supply road was established in 1878 and was used till 1886.  The east portion of the route was in gumbo and when wet was almost impossible to travel.  It ran from the mouth of Landing Creek to near Dixon and westward to Rosebud, Pine Ridge, and the Black Hills.  The name dates back to the early days of steamboats on the Missouri River.  They made a practice of stopping at the mouth of this creek to land supplies for transfer overland to the Indian Agencies and the Black Hills.  Gradually the creek became known as “the landing creek.”   It was referred to as “Rosebud Landing” on early maps.

In the early 1900’s, one of the most noted hills along the old government trail which lead from Fort Randall to the Rosebud agency and the Black Hills was then known as “Gregory Heights.”  This flat topped butte was the most noted landmark along the road westward from Fort Randall.  It was at this point where the road to Chamberlain and Pierre branched off to the north.

The March 6, 1908, edition of The Norfolk Weekly News-Journal reported:  “The flag waving from a tall staff on the buttes is visible for many miles across the beautiful rolling prairies of the reservation.  It is an inspiring sight and one which will be witnessed by thousands who come to Gregory during the coming summer to register for the Tripp county land opening.”

Governor Charles Herreid argued for better roads in his message to the legislature in 1903.  Although he argued logically and forcefully the folly and waste of the existing system at that time, no response came from the legislature.  At that time the automobile industry was in its infancy and the few machines on the road in South Dakota were regarded as a menace to public safety.

Author Clarence Shoemaker, originally published in the Gregory-Times Advocate on October 16, 2019