Shepherd was named for R. E. Shepherd, president of the Billings Land and Irrigation Co. and the Merchants National Bank. The area was originally people with Dutch, German and Scandinavian farmers who arrived in emigrant trains. The land, which had once been cattle country, became farmland after the Billings Bench Water Association canal, a sixty-five mile lifeline for crops, opened in 1905. Homesteaders came, dreamed and hoped, but as in much of eastern Montana, they finally succumbed to drought, grasshoppers and coyotes. By 1950 the land was back to cattle range. (from Cheney's Names on the Face of Montana, Mountain Press Publishing Company)
Shepherd is sixteen miles northeast of Billings. Shepherd is also near Lake Elmo, a 64-acre reservoir that is a popular swimming, boardsailing, boating (nonmotorized), and fishing area. Pictograph Cave State Park features pictographs more than 2,100 years old, and approximately 30,000 artifacts, ranging from stone tools, weapons, paintings and the instruments used, have been identified from the site. The park has paved trails to the caves, with interpretative displays along the route identifying and explaining the natural features, the prehistoric paintings and vegetation found in the area. Pompeys Pillar National Monument, 30 miles east of Billings, is another significant historical site in the area. In 1806 Captain William Clark carved his signature and the date in this rock.