The Erie Railroad Company was incorporated on April 24, 1832, but construction begun in 1836 was delayed by rugged terrain, the financial crisis of 1836, political opposition, and a disastrous fire in New York City that bankrupted many backers; by 1842 the company was deeply in debt, and with aid from New York State work continued. The first pick was struck at Callicoon on March 14, 1847, the first engine passed through in December 1848, and the Erie officially opened for business in May 1851. An excursion train celebrating the opening carried President Fillmore, Daniel Webster, and State Senator James Clark Curtis; although it did not stop as scheduled in town, local businessman Peter Traynor handed a prepared banner to the brakeman as it passed reading, "The Iron Horse from the Hudson is Welcome to Drink of the Waters of the Callicoon." In 1847 Callicoon Depot had only one house, but thousands of laborers from Ireland and Italy came to lay track, and some remained to establish homes and businesses, helping Callicoon become the most important business station between Port Jervis and Susquehanna. That same year surveyor Solomon Royce promoted northwestern Sullivan County with German-language handbills and circulars and developed a lucrative real estate business; more than 250 German families settled in the towns of Cochecton, Callicoon, and Fremont. On March 1, 1869, the Town of Cochecton was divided and its western portion renamed the Town of Delaware, which now includes the hamlet of Callicoon. The depot had indoor and outdoor ticket windows opening to the station agent's office, a passenger waiting room with a large round radiator, the station agent's office and ticket counters on the east side, and the Western Union Telegraph office on the west side. Limited trains stopped only with advance notice of boarding passengers, newspapers were tossed from trains at the station, and mail bags were hooked to a pole so conductors could retrieve them without fully stopping. Callicoon Depot was renamed Callicoon in 1906. Erie trains brought resort visitors in summer, including a Saturday Callicoon Special arriving at 6 p.m., and summer visitors continued arriving aboard the Erie until the 1960s. Steam engines once took water from a stone octagon tower near the old Olympia Hotel before diesel engines replaced steam in the 1950s. The original station between Upper and Lower Main Street burned in 1898, and the present station was built in 1899.