The following was provided by "Rowayton on the Half Shell" by Frank E. Raymond (printed with permission by the Raymond Family)
Rowayton’s first schoolhouse of record was built by such a school “society” soon to be designated the “South Five Mile River School District”. School districts often crossed town boundaries. Ours was comprised of residents of both sides of the river, as did the Middle and Northern Five Mile River School districts (Brookside and West Norwalk). The Southern District was organized in 1820 and promptly set about providing a schoolhouse, one room, measuring maybe 12 x 15 feet. It was located across the road from the property of Andrew Bell who probably donated the site, now 11 Hunt Street. The teacher is reported to have received sixteen dollars a month (a bit excessive for that day, if true) and boarded in the neighborhood.
When the building was replaced in 1895, it was sold to a former associate editor of the South Norwalk Sentinel, Emma Walker. Miss Walker had the older part of the school detached and moved across and up Cudlipp Street where it still stands as a residence overlooking the White Bridge. Part of the read section also survives, having been incorporated into the residence at 3 Cudlipp Street.
In the early 1890’s the local school district acquired property at the corner of Witch Lane and Rowayton Avenue from Capt. Edward Smith, a natural growth oysterman. A two-story, four-room school, complete with full attic, basement, bell-tower and separate outdoor privies opened in 1894. A soaring flagpole stood on the front lawn and a steep hill, ideal for sliding and romping, was close behind the building that was to serve as the Rowayton School for nearly fifty years.
Rowayton children going beyond elementary levels commuted to and from classes in South Norwalk by train and later by trolley.
In 1913 Norwalk, South Norwalk and East Norwalk consolidated into one governmental administrative unit-The City of Norwalk. With consolidation came a single city-wide school system. The Rowayton School was deeded to the city Board of Education. The South Five Mile River School District ceased to exist.
Attendance at the old wooden schoolhouse on the Rowayton Avenue-Witch Lane corner had long since surpassed the capacity of the four room to house kindergarten, plus grades one through six, by 1939. The City of Norwalk, through its Board of Education, also acquired a tract of the Raymond estate north of McKinley Street east of Roton Avenue. The tract measured approximately ten acres and contained a large pond. The sale price was $10,000. The following year the present Rowayton school building opened. The acreage was filled and landscaped, playgrounds for the young and old installed-jungle gyms, softball fields, tennis and basketball courts-all resulting in a fine outdoor facility.
Two large additions to the school were added between 1950 and 1970, and again in 2015 to meet what seemed to be an ever-increasing demand.
The second Rowayton School was built in 1848 on the river bank at the intersection of Cudlipp Street and Rowayton Avenue. Although larger and more comfortable than the first school, a second room had to be added some twenty year later. A reporter for the Norwalk Gazette visiting the village in 1869 “noticed the foundations going up for a considerable addition to the schoolhouse in Grantville, more than doubling its present capacity. More room for scholars’ seemed to be the cry all over the town – thanks to the benevolent law.” The school was a long narrow building facing the street on what is now 1-3 Cudlipp Street. The school was divided into two rooms, one called the “big” room and the second, of course, the “little” room, although according to pupils of the time, the rooms were about the same size. The addition was a square section added to the read of the building, making it “L” shaped.
The teacher in the “big” room also served as principal. Both the “big” and “little” room teachers came to school by train from South Norwalk, and walked down “Main Street” from the station. One was very conscious of the daily temperature and invariably read the outdoor thermometer each morning, the students were well aware of his habit. On cold mornings the big boys would put the thermometer in a bucket of ice where it was left until the teachers approached to within sight. Then the thermometer was hastily re-hung on its nail by the door. When the principal looked at the doctored instrument, he decided it was too cold to hold classes. School was cancelled for the day!