The contents of this Special Issue of Agroforestry Systems are from selected papers presented at the 16th North American Agroforestry Conference of the Association for Temperate Agroforestry held at Oregon State University in Corvallis, Oregon, from June 24–27, 2019. The conference attracted over 150 participants and the event included oral presentations with seven concurrent sessions, poster presentations, a pre-conference tour, one full day of field tours, plenary keynotes, and Agroforestry Working Groups and Regional Meetings. The seventeen manuscripts included in this Special Issue have been derived from temperate agroforestry research projects, outreach, and development. Papers were selected from temperate regions in North America, including the United States, Canada, and Mexico as well as manuscripts from sub-tropical systems in India. Overall, the conference papers addressed multidisciplinary topics in agroforestry including, accessing resources, accessing markets, managing risks, advances in technology applications, production science, environmental benefits, adoption, implementation, evaluation, education, outreach and community engagement, policy practice, climate change opportunities and challenges, and special forest products.