As the whaling industry was declining there was little more in town than the courthouse and the county jail to provide jobs. Attempts made to start new businesses were not long lasting. Thus, Edgartown businessmen proposed a direct road along the beach from Oak Bluffs to Edgartown, hopefully cutting travel time and attracting more business their way.
When a development called Ocean Heights was laid out overlooking Sengekontacket Pond, soon followed by one on Trapp’s Pond, Edgartown welcomed the enterprise. After the Daniel Fisher oil manufactory was bought by the Dukes County, the only new construction in town would have been the Jail.
In March, 1874, Oak Bluffs developer Erastus Carpenter and Edgartown’s leading businessman and politician Samuel Osborn, Jr. met with potential investors to discuss the building of a railroad between Cottage City and Edgartown. Interestingly, two of those possible investors were whaling Captains Jared Jernegan and his cousin Nathaniel Jernegan. Nathaniel had become the sales agent for the Katama Land Company and was most optimistic that the railroad would be a success. It would, he said bring a “handsome profit” and the town would make money on its investment.
Martha's Vineyard Museum