Digital methods provide archaeologists with ever-increasing opportunities to collect more data about the past in new formats. These larger evidentiary datasets, in turn, help us to address questions about the human past with increasing precision. To take full advantage of these opportunities, archaeologists must develop digital literacy skills and learn how to lead digital projects. Here, we describe seven digitally-based projects we have undertaken at the University of Pennsylvania in order to create new tools for archaeological data collection and sharing, as well as to test collaborative models for the digital humanities programming process. In these projects, archaeology students work directly with engineering students. Through this interface, the students from both areas gain valuable transdisciplinary experience while experimenting with new ways to accomplish programming goals and to collect archaeological data. The learning potential for these students was a key motivation for our initiative. Our projects have already led to several websites and digital applications that are available as open source downloads. We present our impressions of this collaborative process with the goal of encouraging other archaeologists to form similar digital humanities partnerships.