From the first school built in 1881 on the "Old Mound" with an enrollment of 42 local students to an enrollment of 134 senior students from several communities, Pilot Mound School has undergone many changes in enrollment, location and buildings.
The mound 2 miles northwest of the present town site of Pilot Mound was the location of the first school built in Pilot Mound School District No 25. Within five years Londesboro, Marringhurst, Gowancroft, Wood Bay, Floral and Copperfield Rural School Districts had formed. Pembina and Stuartville were established in 1889 and 1894. The rural school of Goudney was the only school district to precede Pilot Mound School District.
When the long awaited railroad arrived in 1885, only to bypass the town site by two miles, the town gradually relocated near the rail line. Two years after the first school was moved to the present town site in 1887, it became too small and R.Blackburn erected a two-story structure, later known as the "old red school", at a cost of $1985. For $1600 a fourth classroom was added in 1895.
After slightly modifying plans for a four-room brick structure with spacious halls and cloakrooms, a basement playroom, an electric buzzer system, metal ceilings and a round belfry with a large bell, a new school was opened in 1905. Twenty-year debentures were issued to pay for the $14,000 building and site. At that time classes were offered for Grades 1-8. By 1927, the school was overcrowded and the former Methodist church became the Primary room for over 30 years. With expanding high school enrollment and a public demand for Grade 12, renovations were made and the Pilot Mound Collegiate Department was inaugurated in September of 1937. In the early 1950s, the school overflowed into the Parish Hall of the Anglican Church.
The present school, built in 1958 for Grades Kindergarten to 12, has undergone two expansions. The attendance of students from Swan Lake First Nations Reserve in 1964 and the consolidation of rural schools with Pilot Mound swelled the enrollment. Several huts and three temporary classrooms in the gymnasium were used until a four-room addition funded by the Department of Indian Affairs was completed at the south end of the school. Even then, a number of huts were still needed to accommodate the K to 12 students. In 1973, a major expansion added a whole new wing with three classrooms, two laboratories, a library, expanded office and a large gymnasium. For a few years in the 1970s and early 1980s, mobile trailers for courses in home economics, power mechanics, graphic arts and electronics were used. By 1985 all mobile units were phased out but home economics was offered for a brief period from 1994 - 1996. The first wood working shop installed in a hut in 1975 was replaced in 1983 by a large modern detached unit at the north end of the school. In the 1990s two computer labs and an IITV were installed.
Just as the physical plant has changed so has the area served and grades offered at Pilot Mound School. The consolidation of rural schools and the attendance of students from Indian Springs increased enrollment in the mid 1960s to a peak of 365 students. By the 1970s, the high school did not have enough students to offer a variety of courses. The problem was solved by shared services wherein Grades 10-12 students from Thomas Greenway Collegiate, Crystal City, and Pilot Mound School were taught specific courses together and were bussed back and forth between the two schools throughout the day. The addition of students from Glenora in the early 1990s did not prevent the gradual decline of enrollment to the point that the high school could no longer adequately meet the needs of the students. The amalgamation of Tiger Hills and Pembina Valley School Divisions and concern of parents introduced a new concept. All students from Clearwater, Crystal City, Glenora, Mather and Pilot Mound attend Senior Years at Pilot Mound Collegiate while students from the same area attend the Middle Years at Thomas Greenway Middle Years School. For the first two years of the new arrangement, Early Years students attended school in their own communities. Parents, concerned about combined grades in classrooms, asked the Division School Board to consider moving all Early Year students in the area to one building. In 2001, all Early Years students began attending Crystal City Early Years School.
In the 113 years since the establishment of schools in the Pilot Mound area, the education and well being of the student is still a priority.