As the country entered the Civil War era, it became apparent that the stage coach could no longer meet the needs of the growing island. In 1860, therefore, a group of Long Island and Manhattan capitalists resolved to build a railroad from the East River to Patchogue all along the south shore of the island. The directors and president of the LIRR had been approached on several occasions to build such a road, or at least extend branches to the big villages, but they had always refused. It became clear that if a south side road was to be built at all, it would have to be built by independent capital.
Charles Fox of Baldwin was the leading spirit behind the organization of the new road. A wealthy man owning much real estate in Manhattan, a senior partner in the big clothing house of F. B. Baldwin and an alderman in New York, Fox induced a group of other wealthy men to invest in the new project. The Civil War forced the scheme into abeyance until 1865 because of the instability of the money market and the impossibility of obtaining iron. With the coming of peace in the spring of 1865, Fox and his men plunged energetically into the organization and building of their South Side Railroad of L.I. By summer the stocks and bonds of the new road had been printed and were placed on the market. As fast as the securities were sold, the road was to be built and it was hoped that ground would be broken in October.
In the fine Fall weather of 1865 the directors of the road personally visited all the men of means of their acquaintance along the south side towns. Next to Charles Fox, one of the road's most vigorous supporters was Willett Charlick, brother of Oliver Charlick, president of the Long Island R.R., and the deadliest enemy of the whole South Side RR scheme. Willett Charlick lived in Freeport and canvassed that area along with director Samuel DeMott; James Tuttle covered the Rockville Centre area and Martin Willets did the same for Babylon.
Stock and bond sales were slow in coming in. Some persons insisted the road would not pay, while others doubted that it would be built at all. It was hoped to raise by public subscription $250,000 in all. As the year 1865 drew to a close, all but about $40,000 had been paid in.
In January 1866 the road was formally incorporated and it was planned to begin construction as soon as the frost was out
