This scene depicts a cow licking a newly born calf while a shepherd stands near a sheep and lamb. The man is bare to the waist and wears a kilt-like lower garment. He also wears a necklace. Of the three Seasons medals, The Shepherd is the only one that depicts an Indian rather than a Euro-American. An ironic choice since large animal husbandry was more foreign to North American Indians than either spinning or farming.

The Washington Seasons medals depict scenes of agricultural life that the Americans wanted the Indians to adopt. Ordered by James McHenry, Secretary of War in 1797, the medals were struck in England in 1798. These medals were designed by John Trumbull, a well-respected early American artist and Colonel in the Revolutionary War.
Although the reverse legend on the medals is SECOND PRESIDENCY OF GEO. WASHINGTON MDCCXCVI, these medals were not distributed until after President Washington died. Lewis & Clark may have taken some of them on their cross country travels.