The Office of the Wyoming State Archaeologist has as one of its main objectives to actively engage the population of Wyoming in archaeological stewardship. To achieve this goal, in the past five years, we have launched the youth-oriented Summer Ventures program and the adult-oriented Wyoming Avocational Archaeology Training Program. Both programs were inspired by existing programs in other parts of the country and were launched following research and target audience surveys on how to best adapt them to Wyoming. Despite this preliminary research, our in-field experiences over the past few years have shown some patterns that are causing us to rethink both programs. This article discusses these initial in-field testing years, the issues we have encountered, and the ways we are redesigning both programs to better target the appropriate audiences in light of the different lifestyles of populations, particularly those of youths, in a rural state.