Place names are important markers of the history, identity, ecology and character of the landscapes they exist in. Renaming places may occur in response to social, political or other factors that drive the re-evaluation of what types of place names should be used in contexts. Trail names are one type of landscape feature that also merits evaluation to understand what types of meanings they represent. In this paper, we analyze the social, historical, and ecological aspects of trail names in the state of Maryland, USA. Compiling and tagging over 900 Maryland trail names (largely from state-level land manager databases) we found that many names referenced the type of trail, water features, man-made or built environment features, and landforms. In addition, we found some spatial clustering of trail name themes, such as that many names surrounding Baltimore city reflect an industrial past, conveying a unique sense of place for that region that is rooted in a specific historical period of settler colonial industrialism. We also found that the meaning of and history behind some trail names is not immediately apparent without additional understanding of local historical or cultural contexts. To better communicate these results back to the public, we created an online interactive map that discusses some of the meanings of trails in this region and shares our tagging code. Finally, we argue that future work be conducted on trail names that both expands the spatial scope and types of protected land areas examined as well as considering using crowdsourcing platforms or engaged social research to better understand how trail users and their communities perceive and experience the meaning of various types of trail names.