In the later half of the eighteenth century that the hamlet acquired the name "Shrub Oak Plains," coming about due to the presence of Shrub Oak trees, which formerly thrived in the local sandy soil. Shrub Oak is one of the few places in Westchester County with sandy soil; many of these trees grew in the hamlet area. Described in garden encyclopedias as shrubs or small trees growing to about 10 feet tall, they favor sandy or rock soil that is excessively drained, and abound in such areas.
The sandy soil is Shrub Oak comes from a glacial lake, which once filled the area to the east and north, and ended at the foot of Piano Mountain. The lake eventually drained itself, but the glacial sands and gravels that lines its bottom remained and became a water reservoir that still stands ready to serve Yorktown in time of emergency. Shrub Oak had the only post office by that name, although there was a fire station in the Pocono Mountains called Shrub Oak, where the trees are the dominant vegetation.
By the time of the Revolutionary War, the village of Shrub Oak consisted of eight buildings clustered about Main Street. Presumably, most of these were dwellings. In addition to Main Street, Hufeland indicates that Route 132, Barger Street, and Mill Street had already been laid out by this time. After the Revolution, by 1789, there was built in the village a Methodist Church - one of the first in the county - upon land owned by Pierre Van Cortlandt, Jr.
In 1829, Shrub Oak acquired its post office, the word "Plains" having by this time been dropped from its name. Today's post office at Shrub Oak is the oldest existing in Yorktown Township. In the 1840's, the village of Shrub Oak experienced what has been described as a "building boom"; the stately Darrow-Migliaccio house on Main Street being an example of the type of home constructed during this period.
Just after the Civil War, the village proper boasted at least 23 dwellings, a post office, Gilbert Darrow's "Hall & Store", William Roake's store (which now contains the delicatessen opposite the library), a Methodist parsonage, a cemetery, a Methodist Church, a school house, the office of Dr. James Hart Curry, William Lee's "Shoe Shop", Henderson's blacksmith shop, Tredwell's Wheelwright Shop, and the Willow Brook Preparatory Academy (also known as Dr. J. Richard's Classical School), it was the most advanced. The full import of this will be realized when one considers that the Yorktown of 1867 consisted mainly of scattered farms.
Very early then, Shrub Oak acquired a distinct identity. This also came about due to the personages who inhabited the village. The 1860's and 1870's was a classic time there, often spoken about by the old people in this century. There was the Reverend Benjamin Currey, the abolitionist and Underground Railroad "conductor", who styled himself "the poor man's preacher", because he would not accept payment for delivering sermons. His son, Dr. James Hart Curry, an army surgeon during the Civil War, was one of the early physicians in the region. Then of course, there was John Coleridge Hart, born in the Hart homestead on Stony Street, who made a fortune in pharmaceuticals in New York City. His residence upon Main Street, built in the 1820's, now houses the library dedicated to his memory.
Prior to 1900, there was a lot of wealth concentrated in Shrub Oak. The year 1920 saw a Shrub Oak that was much the same as the 19th century village, with one very important exception; for it was in that year that Yorktown's first library was established, the John C. Hart Memorial Library, in the former home of its namesake, whose daughter, Mrs. George Dresser, M.D., had willed it to the township on the condition that it be utilized as a library.
Hart Library Shrub Oak NYThe construction of housing developments began in 1927 with Sunnyside Estates (Sunnyside Avenue area).Construction has accelerated in the Shrub Oak area until the 1950's when the village was almost been surrounded by subdivisions. Since the 1950's, the bulk of the hamlet's population has changed from those descended of old families to newcomers from New York and elsewhere. Today the old village of Shrub Oak itself has not change drastically since the 1860's. The historic areas of Main Street and adjacent streets should be preserved in a landmarks preservation area. An historic district would preserve the beauty of Shrub Oak; deter robbers and vandals; and unite the village through pride.
In 1929, the small rural school districts of Jefferson Valley, Mohegan and Shrub Oak were consolidated into "Central Rural School District #1, Shrub Oak, New York." For this new central district, a charming red brick school was erected next to the Hart Library in Shrub Oak, which contained grades 1-12 and thus offered the children of northern Yorktown a local high school for the first time. The core district of the Lakeland Central School District that was later formed in 1951. In 1952, the Lakeland Central School District opened its doors for the first time, serving parts of the towns of Yorktown, Cortlandt, and Somers in Westchester County, and Carmel, Philipstown and Putnam Valley in Putnam County. The original red brick school is currently in the process of being converted into the administration building of the Lakeland district.