Annie Whittingham, known as Sweet Annie for her kind, loving spirit and eagerness to make friends, died in a tragic accident in August 2019 one week after starting kindergarten while playing in her Fox Chapel backyard with her father and sister Sadie. As the Whittingham family grieved, the Fox Chapel community responded with an outpouring of support through condolences, donations, meals, and messages of love, far surpassing an initial fundraising goal. Seeking to give back to the community and create a lasting connection to Annie, Abbie and Steve Whittingham envisioned Annie's Field of Dreams at McCahill Park, inspired by the quiet park where Annie had often played and learned to walk. Drawing on Annie's favorite activities and imagination, they developed a playground with swings, a rocking dog, a play village, a book lending library, benches for reading, and a one hundred-foot zipline, with additional features planned to serve community needs. Supported by Fox Chapel Borough Council and funded through the Annie Whittingham Forever Five Fund managed by the Pittsburgh Foundation, the project reflects both Annie's joyful spirit and the community kindness that carried her family through their loss.