A two-year course taught by Thomas Gimbrede, a French-born miniaturist and engraver, at the school’s Drawing Academy, gave Eastman training in sketching the human form, landscape studies, and topographical drawing. The purpose of the course was to turn out practical draftsmen with engineering skills who could provide civil services for the developing nation, but drawing was also deemed valuable for processing information and honing perception.

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Although otherwise an undistinguished scholar, Eastman graduated in 1829 at the top of his drawing class. The new second lieutenant’s first assignment took him halfway across the continent to Prairie du Chien, Wisconsin. There Colonel Zachary Taylor was rebuilding Fort Crawford–originally of log construction–with native rock. An exacting pencil sketch that Eastman made of the soon-to-be-demolished post and fledgling Prairie du Chien is the earliest extant example of his meticulously drawn military landscapes.

Early in 1830, Eastman was transferred 150 miles up the Mississippi River to Fort Snelling, then the country’s northernmost frontier post. Built in the wake of the War of 1812 to block British infiltration of the American Northwest and to protect the newly organized fur trade by maintaining peace among the Native Americans in the region, Fort Snelling was a stone behemoth situated on high limestone bluffs above the confluence of the Mississippi and St. Peters rivers in Minnesota.

While at Fort Snelling, Eastman used some of his free time to sketch the untamed beauty of the surrounding, pristine northland. His drawings from this period have been lost, but he is known to have always carried a sketchbook and pencils in his saddlebags. Landscape sketches of Fort Snelling and the Upper Mississippi Valley made in 1830 and ‘31 served as studies for oil paintings that Eastman completed when he later returned to the East.

Records indicate that Lieutenant Eastman satisfactorily carried out his duties at Fort Snelling. The Minnesota frontier was relatively quiet; only rarely were soldiers dispatched to put down Indian trouble. In fact, many of the officers, including Eastman, were cohabiting with Indian women. In 1831, when Eastman was transferred to topographical duty in Louisiana, he left behind a Native-American wife, Stands Like a Spirit, third daughter of Chief Cloudman of the Lake Calhoun village, and an infant daughter, Nancy Eastman.

After assisting with a railroad survey in Louisiana, Eastman served briefly with the Topographical Engineers at New London, Connecticut. Then in January 1833, he was recalled to West Point. His former drawing teacher, Thomas Gimbrede, had died, and, while the Academy sought a permanent replacement, Eastman assumed the hastily-created, temporary position of assistant teacher of drawing. The “temporary” assignment lasted for seven years. Gimbrede’s job finally went to Robert Weir, a landscapist of rising reputation with whom Eastman studied privately.

Preferring the outdoors to classroom duty, Eastman twice–in 1835 and ‘38–applied for a transfer to the Topographical Engineers, but to no avail. In the meantime, always giving his best to whatever occupied him, he proved to be a conscientious and productive instructor. In 1837, he prepared A Treatise on Topographical Drawing, a small book with folding plates that became the official text for classes at West Point.

These years at the Academy were happy ones for Eastman. In June 1835, when he was 27, he married 17-year-old Mary Henderson, the daughter of West Point’s assistant surgeon. An able young woman, who expressed herself well in prose and poetry, Mary would capture the fancy of the literary world with several books about Indians, which were illustrated by her husband.

In 1838, the National Academy of Design in New York City exhibited eight Eastman canvases; five were Eastern scenes, the remaining three relied on sketches he had made years earlier on the Upper Mississippi. A promotion to captain that year relieved Eastman of his classroom duties and led to his participation in the Second Seminole War in Florida. After a brief assignment at Sarasota, he took command of Fort Fanning, a temporary garrison on the Suwannee River. At both places, Eastman found time to paint not only his usual landscapes, but also, for the first time, the local Indians.

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