Mrs. Emily Grymes tragically loses two of her children in a single year. Elizabeth passes away due to illness, and Breckenridge is lost as a casualty of World War II. Following this heartbreaking loss, Mrs. Grymes begins caring for the children of her friends and neighbors during the day.

Her “daycare” program continues to grow. Friends encourage her to enlist some assistance. A true school having long been her goal, Mrs. Grymes agrees.

She adopts the curriculum of the Calvert School in Baltimore, Maryland, for her first grade students and begins hiring teachers.

At this time, the school continues to operate in the Grymes home.

Spearheaded by Mrs. Carroll Kim Shackelford, a Board of Trustees is formed to facilitate the continued growth and development of the school. 

Mr. and Mrs. Woodbury Ober offer a “seed gift” of 32 acres of land on Spicer’s Mill Road. A caveat requires that the board raise $60,000 in six months. The board meets and exceeds this goal, raising over $85,000! While the new school is under construction, students meet in the second story of the Orange Volunteer Fire Company.

During this year, the school receives its official incorporation from the State Corporation Commission. 

On May 27, 1956, a dedication ceremony is held for the new schoolhouse, today’s Ober Hall. Colgate W. Darden, the President of the University of Virginia, is the keynote speaker at this dedication. He emphasizes the importance of having both public and independent schools. 

During this time, Grymes continues to attract more students, and a used school bus is purchased to transport children from the Gordonsville area.

Construction of du Pont Hall (the current gym) and a new Headmaster’s House (now called the Carrington House) is completed in the mid-1960’s. The “gymtorium” will remain a separate structure from Over Hall until 1985.

Hastings Hall (the library wing) is added to Grymes Memorial School in 1971. The structure is named after Mrs. Rose Hastings, former Headmistress from 1956 to 1966.

Art, science, and homeroom renovations take place. 

These renovations finally connect du Pont and Ober halls, giving the main portion of the school much of the appearance it has today.

Thanks to the support of our generous donors, involved parents, and dedicated faculty and staff, Gardner Hall is completed as a new home for the Upper School.

In the 2014 edition of the Grapevine, Head of School Dr. Penny Work highlighted the benefit of a new “sense of upper school community” as faculty and students learned to “live with the new space, and contemplate [the] next best move as we continue to plan for the future.” 

As we enter the 75th year, the future is bright. The Campaign for Grymes is our “next best move,” with the goal of building for the next 75 years of joyful learning.