Smithtown, A History: The Original School Days

Located at 9 Singer Lane in the Village of the Branch, sitting behind the Dairy Barn, is a store called Naturally Free Food. In the 1800s, this structure served as the first schoolhouse in Smithtown.

Smithtown historian Brad Harris said the school was originally situated across from Singer Lane on Main Street, where Sunrise Golf Outlet was located until recently. According to the land once belonged to Epenetus Smith II, a descendant of town founder Richard Smythe. When it was built, the schoolhouse sat between the Presbyterian Church and Smith’s tavern.

The first evidence of the structure was 1802, according to the scrap-book which was published in 1968. At this time an Articles of Association was formed where residents would pay $10 a share for each of their children to attend. It wasn’t until 1816 that the building was bought by taxpayers and considered a public school.

The structure is also known as the Whitman Schoolhouse. According to Harris, this is due to poet Walt Whitman teaching here during the1837 to 1838 school year. Legend has it that Whitman stayed with the Conklin family and only had one shirt. Every night Mrs. Conklin would wash his shirt and have it ready for him the next day.

In “Colonel Rockwell’s Scrap-Book”, the schoolhouse is described as having a fireplace on the west end. Noel Gish wrote in his book “Smithtown New York 1660 – 1929 Looking Back Through the Lens” that the classroom had no maps or blackboards. The children would write on slate boards with chalk during their lessons. It was unpainted, had no indoor plumbing, and a small, wood stove was used to heat the room.

According to Harris, the Smithtown Union Free School District was formed in 1868. It was at this time that a new building called The Academy was built at the same location as the original schoolhouse. This structure was used until 1908 when it was replaced with a larger building.

When The Academy was built, Harris said a James Darling bought the original school building and moved it to its current location. Darling was one of the owners of a store called Brush and Darling where Dairy Barn is today.

By the time “Colonel Rockwell’s Scrap-book” was published in 1968, Seymour Singer used the structure as a real estate office. The old schoolhouse has also been used as a day spa through the years.

While the schoolhouse is on the historic inventory for Smithtown, it’s not considered a landmark. Harris said Singer had hoped to sell it to the Smithtown Historical Society a few decades ago, but the plans fell through.

which sells gluten-free food products and baked goods, has occupied the building for the last few months. Owner Christine Mitchell said the woodwork, doors, flooring, bead board ceilings and door knobs look as if they were part of the original building.

While the town outgrew the one-room schoolhouse in 1868, and changes have been made to the structure over the years, the building continues to maintain its charm and place in our community.