We consider trails to be a document type of growing importance, authored in abundance as locative technologies become embedded in mobile devices carried by billions of humans. As these trail documents become annotated by communities of users, the resulting data sets can provide support for a host of services. In this paper we describe our sociotechnical exploration of the devices, scenarios, and end-user interactions that will come into play as these tools become widespread. We couch this work in a discussion of the sociological impact of a shift from hyperlinks to hyperties -links that bridge the gap between computational media and physical world interactions. We describe a prototype hardware device for location and other sensor data capture. This device links to a complementary website for querying, sharing, and distributing the resulting route datasets. The web application allows users to find related community members via shared attributes of their contributed or annotated routes....