Evening dinner meetings were held in Centerfield, Brownsboro, Westport, Pewee Valley, and La Grange. The Society was striving to become an organization to preserve and protect the artifacts which had been acquired and to find a place to display these objects for the benefit of future generations. In these early days, the primary programming of the Society featured quarterly dinner meetings with speakers whose topics included local and regional historical subjects. Some of the meetings consisted of storytelling, but the aspirations of the founding members were far from the pursuit of a casual hobby. The desire to become something more led to numerous and frequent meetings for planning and discussion.

In the early 1970's, the Society published CEMETERIES as the first volume in the Records of Oldham County, Kentucky and then decided to begin the research for a book about Oldham County history. The membership in the 1980s was relatively small in number but vigorously active in pursuit of its goals. The Society discovered and collected various artifacts of Oldham County life: maps, birth records, census records, insurance records, death certificates, news articles, city and county records, letters, diaries, and photographs. During this period, an all-volunteer Board managed the Society without any paid staff. The Society operated in this manner for a number of years.

After the death of Mrs. Louise Head Duncan in 1990, the Peyton Head Trust approached the Society to determine if it would develop and use the two properties at 106 and 108 N. Second Street opposite the courthouse in La Grange. First-person accounts recall Society President Chilton Barnett calling for discussion of the topic to pursue property acquisition and board member Carl Klingenfus making the motion to accept the pursuit of the properties as a museum for the Society. The motion passed. A generous donation from the Head Trust made it possible for Chilton Barnett to purchase the parcel of land in the Society's name.

On June 17, 1994, the Society opened the James Mount House after a thorough restoration. This was a significant milestone: For the first time in its history, the Society had a visible presence. Today, this building is called the J.C. Barnett Library and Archives in honor of the Society's long-time President and benefactor, J. Chilton Barnett. It contains office space; limited collections storage; and meeting space for the Board, volunteers and docents.

In September 1995, the Society hired its first full-time professional director. In 1996, the Society published History and Families, Oldham County, Kentucky: The First Century, 1824-1924. In August 1999, the Society's dream to operate a professional museum facility was realized with the opening of the Peyton Samuel Head Family Museum.

In 2001, the Society purchased the former LaGrange Church of Christ building which sits just behind the Museum, thereby safeguarding the integrity of the entire block as the History Center campus. Plans are underway to renovate the church building with the intention of using the space for additional programs and exhibits.