By an act of the New York State Legislature on April 9, 1795, money was allotted to Suffolk County for free schools, and on June 23rd of that year the supervisors of the nine towns of the county met and apportioned funds. While the amounts allotted varied from year to year, this system continued until 1812 when an act for the establishing of common schools was passed. Under this law, which continued in force for many years, a certain sum was allotted to the county to be apportioned among the towns, each town then raising by tax " ... as much money as is granted to said town by law for the Common School fund."
The first schoolhouse that served the inhabitants of Islip was situated at the fork of the road near where the Pavilion Hotel stood, this now the general area of the southwest corner of Montauk Highway and Suffolk Lane, East Islip. When it was first built and how long it was at this location is not known. About 1808, it was moved to the newly purchased property on the north side of Main Street, in Islip, generally opposite the Islip Theatre.
The earliest record of a school inspection occurred in the building of 1808 on March 2, 1825, when the school inspectors, Medad Rogers, Tredwell P. Scudder and Henry Brewster recorded that School District #2 "excelled" in "Reading, Geography and Book Keeping." "Writing, Arithmetic and English Grammar" was not graded. There were 36 "Scholars Attending" and Henry Brewster was the (only) teacher.
At a school meeting of April 10, 1828, a resolution was passed for a new schoolhouse. Then, as now, there was apparently a great outcry because of the expense, and an appeal was made to Judge Selah Strong, of Setauket. He found a legal flaw in the proceedings, but after a few months this was overcome, and $400 was voted for the new schoolhouse, to be built on the same site of the old one. The playground must have been the street as the land bought was only 20 x 40 feet! E(benezer?) Hawkins was the contractor and Silas Whitman, the carpenter. This school of 1828 had a narrow recitation bench on the south side of the room about eight inches wide and a deep, sharp moulding projecting from the wall just high enough from the seat to make sitting uncomfortable. A stove stood in the center of the room.
In 1853, the schoolhouse (of 1828) was sold for $165. It was moved to a spot about sixty feet east of N.O. Clock's house and used by the Methodists for a class room. It was afterwards bought by Henry Clock, and is now used by Dr. Hamill as a barn.
The next schoolhouse, built in 1854, one storey in height, was considered a grand affair when first built. A precautionary resolution was passed that the building should not cost over $859 complete. The site was bought the previous year for $250.
On September 22, 1865, District #2 became a Union Free District with one school and 200 pupils.
In 1869, the one-storey schoolhouse of 1854 was raised and another ,storey built under it as an expense of $1,200.  Hammond Marvin took the contract for raising the building, and Robert Hubbard did the carpenter work.
In October, 1884, a resolution was adopted to appropriate $10,000 to build a schoolhouse ($2,500 for the land), which is now completed on Monell Avenue, and which is said to be the most perfectly-adapted school building in all respects in Suffolk County. 
 'Since the annual meeting "of the freeholders and inhabitants of the Town of Islip" took place April 7, 1795, two days BEFORE the act of the State Legislature, the first reference to the act occurs in the Town of Islip Minutes of the following year. At a meeting "held the first Tuesday in April A.D. 1796," Tredwell Scudder, Supervisor, the following were appointed Commissioners of Schools: Richard Udall, Nathaniel Conklin and Nehemiah Higbie. Carl A. Starace, compiler, Book One of the Minutes of Town Meetings and Register of Animal Ear Marks of the Town of Islip 1720-1851, Town of Islip, Islip, N.Y., page 72.
There is no record of any amount of money associated with the act although on page 431 of (unpublished) Town of Islip Minutes, under the date of April, 1800, the following is found: "Cash collected on the ... of Schools in the year 1797 - 13 pounds, 7 shillings and 9 pence." Unpublished Town of Islip Minutes, xerox, pages 78 and 431.
 Under the Act of 1812, towns were divided into school districts~ Islip became School District #2.
 Much of the early history of the Islip Village schools contained in this paper was taken from two sources: An unidentified, undated newspaper article, "Memoir of the late Rev. Amos Doxsee, of Bay Shore, Read by P. J. Hawkins before the South Side Teachers' Association at Islip." The other source is an article, "Taking Leave of the Old Schoolhouse in Islip, N.Y., by P. J. Hawkins a paper read January 1, 1885." This (second) source was further identified as "Copied at the Long Island Historical Society from a typed copy loaned by Nathaniel R. Howell, 1956." I believe the newspaper article was adapted by P.J. Hawkins from his address delivered on January 1, 1885.
Apparently P(hilander) J. Hawkins' paper was delivered at the time the "Monell Avenue" school was first occupied but delivered at the 1854/1869 schoolhouse on Main Street.
The "Old Schoolhouse" from which they were "Taking Leave" was the school building built in two sections, 1854 and 1869, formerly located on Montauk Highway, Islip, directly opposite the Islip Theatre, on the north side of the street adjacent to the sidewalk. The Islip (Garrup’s) Plumbing Company last occupied the building which was demolished in the 1960's when the parking lot was put on the site.
A map of 1873 shows the school building to be about two hundred feet from the road on the north end of the property.
 Hawkins, "Taking Leave," p. 1. This statement not found in Hawkins' "Memoirs." Hawkins states: "It was only about twenty years previous (to 1828) that the very first schoolhouse ever known in Islip village was put up about the same site as the later one (the school building of 1828)." "This (first) temple of learning was erected about 1808. There were only eight or ten houses in the district." The place where the c. 1808 school was first built is unresolved.
 Document, District Office, Bay Shore Schools, Bay Shore, N.Y. Another document records inspections in District #2 in 1825 (2) through 1830, 1834 through 1839. The number of "scholars" in each subject is also given.
 Hawkins, "Taking Leave," p. 3. Hawkins, "Memoirs" says only, "The schoolhouse of 1828 cost $400 and was considered by many a very extravagant affair."
 Hawkins, "Taking Leave," p. 4.
 Hawkins, "Taking Leave," p. 4' . Hawkins, "Memoirs", says that Mr. (Amos) Doxsee was instrumental in the erection of the present building, in 1854, and taught five years afterward."
 Hawkins, "Taking Leave," p. 4
 It was in this school that P. J. Hawkins delivered his memoirs" address. Hawkins," Taking Leave," p. 4, "The schoolhouse in which we are convened tonight… "
 Hawkins, "Taking Leave," p. 7.