In 1729 the first school was established in Greenport, then known as “Sterling”. It was attended by boys only. The curriculum consisted of the “three R’s”, the most important of which was considered to be ‘rithmetic. By 1805 the census had risen to thirty-one pupils, six of whom where girls. The first school building built in Greenport after the adoption of its first name was located on the east side of First Street.
The village changed its name so it would get a federal post office. In 1831 the following resolution was passed:
“Resolved, that the village hereafter be called Green Port. This village was commenced in the Spring of 1828, and is now a place of considerate and increasing business. There are now fifteen dwelling houses completed and several others in progress, five stores, a warehouse, and numerous mechanic shops. They are now fitting for Green Port two whaling ships…and a number of smaller vessels employed in the fishing and coasting trade. They have a wharf at which ships lay, or are hauled out, and two sets of ways for hauling up vessels. The land upon which the village is situated and in the neighborhood is of an excellent quality, the prospect very fine, and commanding; and in short, Green Port is a very eligible, flourishing and beautiful place.”
When his passage was written, Greenport was at the beginning of the whaling era. The first ship, the “Jane A. Bishop”, was built in 1836. Greenport was booming. Steam boats began running that year. Soon there was a fleet of twenty ships sailing from Greenport.
In July, 1844, the railroad made its first run for New York. Greenport was accessible to the wealthy “city people”. For quite some time Greenport was the “in” place to be. Then quite suddenly in 1860 the whaling industry ended, but Greenport prevailed.
In 1842, Walt Whitman taught one successful term at Greenport. While here, he published “The Watchman”. Afterwards, he moved to Southold and taught there.
On August 5, 1861, a special meeting was held to discuss the formaation of a union free school. Only men were allowed to vote. On August 13, a final formation of a new district and school was formed, with only forty-nine against votes.
In 1879, the Lillis property, owned by William Wickham, was bought and on March 4, 1879, plans for a new building were under way. The census numbered three hundred thirty-five. In August the new building was completed. That year an Academic Department was formed and Greenport had an entirely new curriculum.
By 1889 the school had progresses to the point where a committee was developed by the board to raise the question of placing the school under the Regents system. In 1890 this was accomplished and one student earned a Regents diploma.