 In 1868, he organized and served as president of the New York and Oswego Midland Railroad (NY&OM), a route traversing much of New York State on its way to New York City.He also established a steamboat service connecting Long Island to his new railroad.In 1870 the Republican state convention nominated Littlejohn for Lieutenant Governor of New York on the ticket with Stewart L. Woodford, but he declined to run.