Several portions of modern NY 38 were originally part of turnpikes and plank roads during the 1800s. On April 13, 1819, the New York State Legislature passed a law incorporating the Cortland and Owego Turnpike Company. The company was tasked with building a highway—the Cortland and Owego Turnpike—from Owego north to the then-village of Cortland. This route roughly followed what is now NY 38 north from Owego to the vicinity of Harford, where it would have turned north to access Virgil, then continued to Cortland by way of modern NY 215. A property dispute case in 1965 showed no evidence of this turnpike having been built.

         On April 13, 1825, the legislature chartered the Auburn and Port Byron Turnpike Company. The Auburn and Port Byron Turnpike began at the Auburn State Prison in Auburn and proceeded northward along the routing of NY 38 to meet the north branch of the Seneca Turnpike in the town of Brutus (now Throop). From there, the turnpike continued on NY 38 through Port Byron to the Seneca River, where it ended at a bridge crossing the river at Mosquito Point. In 1851, the Auburn and Moravia Plank Road Company was incorporated. They were tasked with connecting Moravia to Auburn by way of a plank road along the western side of Owasco Lake (now NY 38).

          The company was organized in 1848, its largest shareholder and president was David Wright, of Auburn, New York. Wright was an Auburn, New York attorney, the law partner of William H. Seward, he was the husband of Martha Coffin Wright, whose sister was Lucretia Coffin Mott. From documents in the collection, we learn that he held 433 shares of the company’s stock.