Throughout the 19th and into the start of the 20th centuries, Pelham did not offer public high school education.  Children either went to private school (including boys to the "Taft School," then located in Pelham, or girls to "Mrs. Hazen's School").  In fact, many towns and school districts in New York did not have high schools until well into the 1950s and children from those towns often went to neighboring towns for anything beyond eighth grade with the cost paid for by the child's home district.  In the case of Pelham, kids could go to Mount Vernon or New Rochelle for public high school.  The construction of the building that is now Siwanoy Elementary School made public high school education in Pelham possible for the first time in September, 1910.

Plans for a new high school began with a special taxpayer meeting on November 13, 1908 to vote on a proposition to purchase a site for the new school.  According to news reports from the time:  "At that meeting the present site was decided upon and the Board of Education was instructed to purchase the same and to issue $70,000 in bonds" to purchase the land and construct the new school.*  York & Sawyer, a firm well-known for major college building commissions, were retained as the architects and Smith Brothers had the winning bid as contractors (a local firm that would go on to build many of Pelham's  landmarks, streets and infrastructures).  The cornerstone was laid October 23, 1909.

In addition to adding high school classes on the top floor, the building also consolidated two earlier elementary schools into "Siwanoy Grammar School."  (A third, "North Pelham Elementary School" (on the site of the current Hutchinson School), was renovated and enlarged). 

The first "Pelham High School" was dedicated February 1911.  But it was not long before the rapid development of Pelham and the outstanding reputation of the new school led to significant increases in enrollment that outgrew the size of the facility.*  By 1919, there were over 100 students enrolled in the high school, studying alongside children in grades k-8 in a building that was less than one-third the size of the later expanded and current Siwanoy Elementary school.

* Pelham Sun, February 18, 1911

Plans for another new high school stem from February, 1917 with the establishment of a "School Extension Committee" formed "to take up the problem of making provision for the ever-growing needs for increasing the educational facilities of the district."**  The architectural firm of Tooker & Marsh in New York City was selected through a competition sponsored by the American Institute of Architects.  Multiple firms competed and the selection was made by a broad-based committee, including residents with art and architecture experience, who later contributed to the interior decoration of the building. 

With World War I having ended the year before, the whole town turned out to celebrate the laying of the cornerstone on October 18, 1919 for "Pelham Memorial High School," which would be dedicated to those who fought and died in "the Great War."

**The Pelham Sun, April 28, 1922

The dedication ceremony on May 6, 1922 put Pelham on the map as having one of the premier high school facilities in all of Westchester County.  The architectural style was described at the time as "Collegiate Gothic," a style that lent itself well to the use of gray granite as the primary facade material.   The center entrance pavilion was, and remains, the most significant architectural component of the building. The center, two-story protruding bay originally had leaded-glass, cross-hatched windows with stained glass crests as insets.  (These regrettably fell victim to modern replacement windows.) 
 
The interior also features outstanding architectural features, including the oval-shaped, stained glass skylight on the top floor.  The auditorium, with its heavy oak detailing, was described at the time as "an unusually artistic chapel with gothic ceilings."

The exterior landscape work was designed by leading landscape architects of the time, Lewis & Valentine.  In addition to tennis courts, the "Roosevelt Athletic Field" (later renamed Ingall's Field) included a running track and a combined baseball diamond and football field. The field was surrounded by an iron fence over which it was to have had "a variety of climbing roses."

Both U.S. Senator James W. Wadsworth and U.S. Congressman Benjamin Fairchild attended. Congressman Fairchild, founder and developer of the Pelham Heights neighborhood who lived at 267 Monterey Avenue stated: "in dedicating this High School building, we are dedicating something which represents not only the last word in high school architecture, but which represents a noble thought in making the development of our educational system as a memorial ... I know what it means, and my heart goes out to every parent whose son went to the war, and my heart gives consoling thought to the parents of those boys who didn't come back."

Congressman Fairchild did indeed know what it meant because he was among "the parents of those boys who didn't come back."  His only son, Franklin Fairchild, was an aviator killed during a training exercise on February 23, 1918.