The Dale Enterprize School was constructed in 1909 to replace the Piney Grove School. The new school was built on the same property as the Piney Grove School which had been deeded to the Central District School Board in 1877. A provision in the original deed caused some problems when the school was closed. The clause stated that "when the land in no longer used for school purposes, the land shall revert to the heirs of the original donors. By 1963, there were many Heatwole heirs.

According the the 1914 History of Rockingham County Schools, the new school at Dale Enterprize was "a beautiful three-room brick house with water supplied from the Harrisonburg mains. The school was built by Will Rhodes with help from John Corbin and Ike Cole. The Dale Enterprize served the community until 1963 when it was closed and consolidated into the new Pleasant Valley School. The building still stands (1997) and is used as a church.

Teachers known to have taught at Dale Enterprize were:

1909-10 Daphine Rhodes, Effie Showalter

1910-11 Effie Showalter (others unknown)

1911-12 Verdie Rhodes, Effie Showalter, Bertha Spitzer

1912-13 Verdie Rhodes, Bertha Spitzer, Annie Heatwole

1913-14 Bessie Swartz, Effie Showalter, Verdie Rhodes

1915-16 Ella Heatwole, Nora Gowl, Verdie Rhodes

1916-17 Verdie Rhodes, Nora Gowl

1917-18 C. C. Spitzer, Florence Wenger, Nora Gowl

1918-19 Adella P. Williams, Florence Wenger, Nora Gowl

1919-20 Lenna Hamilton, Anita Koontz, Nora Gowl

1920-21 Verdie Rhodes, Nora Gowl

1921-22 Verdie Rhodes, Lottie Swope, Nora Gowl

1922-24 (two sessions) Esther Bowman, Lottie Swope, Frank R. Coffman

1924-25 Walter Miller, Barbara Wright, Pauline Heatwole

1925-26 Hiram Showalter, Barbara Wright, Pauline Heatwole

1926-27 Helen Burtner, Iva Wright, Pauline Heatwole

1927-29 (two sessions) Helen Burtner, Iva Wright, Ada Neff

1929-30 Helen Burtner, Ada Neff

1930-31 Lawrence Bowers, Olive Huffman, Ada Neff

1931-32 Ada Neff (unknown)

1932-33 A. W. Hershberger, Ada Neff

1933-35 (two sessions) Ray Emswiler, Ada Neff

1935-41 (six sessions) Ray Emswiler, Harold Eshleman, Ada Neff

1941-44 (three sessions) Ray Emswiler, Vada Heatwole, Ada Neff

1944-50 (six sessions) Harold Eshleman, Marie Cox

1950-57 (seven sessions) Harold Eshleman, Marie Cox, Alice Keeler

1957-59 (two sessions) Harold Eshleman, Marie Cox, Lucy Hoylman

1959-60 Harold Eshleman, Marie Cox, Mrs. Ruth Hobbs

1960-63 (three sessions) Harold Eshleman, Marie Cox, Mrs. Marian Miller

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