Rowayton’s first schoolhouse of record was built by 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 [Five Mile] River, as were 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. The teacher is reported to have received sixteen dollars a month (a bit excessive for that day, if true) and boarded in the neighborhood.
The Second Home of Rowayton School:
Rowayton Avenue & Cudlipp Street
The second Rowayton School was built in 1848 on the riverbank 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 years later. 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 Third Home of Rowayton School: At the Corner of Witch Lane and Rowayton Ave.
(Old School Field)
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 out-door privies opened in 1894. The building that was to serve as Rowayton’s elementary school for 50 years had a soaring flagpole on the front lawn and was perched at the top of a steep hill, ideal for sliding and romping.
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, citywide school system. The Rowayton School was deeded to the city Board of Education, and the South Five Mile River School District ceased to exist.
The fourth home of Rowayton School:
1 Roton Avenue
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 to meet what seemed to be an ever-increasing demand. A major renovation was done to the school in 1992 and in 2015.
The information above was taken from Rowayton on the Half-Shell by Frank E. Raymond, (printed with permission by the Raymond Family).