Eastern Long Island during the middle to late nineteenth century, especially its south shore, had long been a place of Summer homes and resort hotels; however, the difficulties of travel had limited their patrons to the more wealthy of society. With the advent of expanded rail road service during the latter part of the nineteenth century, this changed dramatically.

While the Long Island Rail Road extended service to Greenport in 1844, its original purpose was to create a “fast” rail/ferry/rail connection from New York to Boston. The needs of Long Island itself were ignored and the chosen route was through the vast, level, but mostly unpopulated plains of the center of Long Island, midway between the established communities of the north and south shores. To maintain fast service, stops were relatively infrequent (there was, however, a station at Yaphank just to the north of Brookhaven hamlet). Eventually, a direct rail link to Boston was construction through Connecticut, and the raison d’être for the LIRR ceased. Other competing rail lines and LIRR branches were constructed; the South Side railroad had extended service as far east as Patchogue by 1869. However, it lacked a convenient western terminus with access to the East River. The various branches and routes were not economically viable, and eventually were merged into a single system. In 1879-1981 the rail line to Patchogue was extended east to Eastport, with stations at Bellport and Brookhaven, finally arriving in Montauk in 1895.

The establishment of rail service along the South Shore made vacationing convenient even for folks of modest means. Hotels and guest houses burgeoned in every community along the south shore, including Brookhaven. The former farming and fishing hamlet became a popular destination, especially for those looking for a “rural” environment. In just a few short years, the fundamental character of the community changed.