More and more Web users ask for contents and services highly tailored to their particular contexts of use. Especially due to the increasing affordability of new and powerful mobile communication devices, they also appreciate the availability of ubiquitous access, independent from the device actually in use. Due to such premises, traditional software design methods need to be extended, and new issues and requirements need to be addressed for supporting context-aware access to services and applications. In this paper we propose a model-driven approach towards adaptive, context-aware Web applications, accompanied by a general-purpose execution framework enabling active context-awareness. Whereas conventional adaptive hypermedia systems address the problem of adapting HTML pages in response to user-generated requests, in this work we especially stress the importance of userindependent, context-triggered adaptivity actions. This finally leads us to interpret the context as an active actor, operating independently from users during their navigations.