The Foundation has undertaken many diverse programs in its first twenty-one years. In 1989, it helped secure a U.S. postal stamp honoring Hemingway. This was a turning point in the Foundation's history. For the first time, national media attention was focused on Hemingway's Oak Park ties. This event also introduced the Hemingway family to the Foundation and its plans for the future.
From 1990 to 1995, the Foundation held an annual celebration of Hemingway, Fiesta de Hemingway, based on the festival San Fermin–the famous running of the bulls in Pamplona, Spain, which Hemingway made famous in The Sun Also Rises. Over 10,000 people attended the Fiesta each year.
Also in 1990 and 1991 the Foundation received significant collections of Hemingway memorabilia, from a Minneapolis collector and from the family of Ernest's older sister, Marcelline. These important contributions led to the development of the Hemingway Museum, which opened July 1991, in a leased space in the Oak Park Arts Center. With the opening of the museum, the Foundation established itself as a key player in the Hemingway world and a significant educational resource for the public.
In December 1992, the Foundation purchased the home where Ernest Hemingway was born and lived until age six. This marked another important transition in the organization, as it assumed the financial responsibility of owning, restoring and operating a historic house museum.
Until 1993, the Foundation was strictly a volunteer-run organization. That year, the first executive director was hired to increase financial support for the Foundation's operations and to create and administer programs that promote public understanding of the organization.
In January 1997, at an event marking the world premiere of Richard Attenborough's film "In Love and War," the Foundation launched a $500,000 capital campaign to support the restoration of the Hemingway Birthplace. In its action approving the campaign, the board of directors set a goal of completing architectural restoration of the home in time for the July 1999 centennial celebration of the author's birth. The campaign eventually raised $1.5 million and after several years of restoration work the Birthplace home re-dedication ceremony was held in November 2001.
Throughout the years the Foundation has hosted an annual conference of international scholars on topics such as "Ernest Hemingway: The Oak Park Legacy," "Hemingway and Other Writers: Contemporaries and Influences" with a focus on author F. Scott Fitzgerald, and "A Hemingway Toast to James Joyce." Proceedings from one of the conferences were published as a book by the University of Alabama Press in the summer of 1996.
Other community outreach programs included educational tours for Hemingway scholars and the public to the Ernest Hemingway houses in Cuba, Key West, Michigan and Idaho; the annual Hemingway Short Story Essay Competition introduced in November 2000 for high school juniors and seniors; and the Annual Books to Brighten Young Minds reading celebration and book donation program targeted at preschool to sixth grade begun in April 2001.