The playground was redesigned and rebuilt, through the generosity and vision of The Wiley Family and their many friends, in the summer of 2012 in memory of Hugh Wiley, class of 2018.
During the dedication ceremony, Erica and Carter Wiley, Hugh’s parents, and Treavor Lord, Head of Hill School, welcomed guests and spoke about the meaning of this project. Erica and Carter said that they “wanted those that knew Hugh to remember him with the happiness and joy he was fortunate to experience on the Hill School playground, and we felt that Hugh’s Playground would capture the spirit of Hugh in a meaningful way…we hope it serves the same purpose for all children in the future.”
The new playground maintains many qualities of the old facility—including plenty of space for sports and imaginative play, a big sandbox, swings, a wooden play structure, and the little red house—while upgrading the equipment, improving the drainage, adding an artificial surface play field and a hard surface play area, installing additional play equipment and creating a more efficient design. 
According to Carter, “support for renovating the playground has been amazing. When we asked that donations be given to the Hill School in lieu of flowers, we had no idea about where to put those funds to work. It slowly came to us that putting them to work in the playground would be fitting and appropriate: the playground was where Hugh was happiest — it was where he could be a little boy. We hope that this playground will do the same for all children in our community. We continue to be moved by support in all forms: people have been — and continue to be — very generous with financial and professional service contributions…from individuals, corporations, and communities near and far.”
Treavor commented that “support for this project from family, friends, and business associates of the Wiley family has been overwhelming. Carter and Erica have shown great vision, determination, and passion in helping to create a playground that will be functional, beautiful, and child-centered. Play provides opportunities for children to experience joy, develop friendships, and learn important life lessons. Hundreds of children in the coming decades will enjoy this playground and benefit from the improvements that are being made in memory of Hugh.”
