By 2029, 20% of the U.S. population will be =65-years-old. American demographics are changing, understanding of the =65-year-old demographic has not. We investigated expectation variables of participants born between 1946 and 1964 in the United States, and identified how expectation trends have changed over time also describing gender differences. We used secondary data from a motivation study published in 2015 to identify the expectations of active older adults. Four years of data were used (n = 71) in a self-selection of four adventure activities (rock climbing, flat-water canoeing, white water kayaking and sea kayaking). Older adults expected experiences in the natural environment, with social factors, and where they were either starting a new activity, or honing acquired skills. They were not focused on danger or the use of personal gear. We recommend programming that caters to an aging population, as well as considerations for gender.