With the rise of web 2.0, initiating and coordinating digital activities in local territories depends less and less on public authorities. The point can be illustrated by the practice of geocaching, a collaborative free-to-play game which connects a private company acting as the organizer, with a community of gamers. New relations to the local territory then emerge between Internet surfers, organized as a collective, and their living space. It is not essentially a matter of existing bandwith or 3G access, but of users being able to participate spontaneously and durably in simple digital services, which are co-constructed and self-regulated. Among the consequences on contemporary territorial dynamics, can be detected a beginning process of spontaneous designation of sites and objects as grass roots everyday heritage and visitable sites, potentially attractive for tourists. This calls for revisiting the definition of "connected territories". Geocaching shows that a territory can become connected, even if it is under-equipped in terms of telecommunications, if those who live in it pass through and discover it, reestablish contact with the local sites through digital services. In this case, geocaching is acting as the vector of this re-connection.