Given the rapidly changing skills needs of post-industrial economies, lifelong learning forms an integral part of government policy within the UK and abroad. However, like the UK, most economies are faced with the problem of how to reach those sections of the community that have traditionally not embraced learning and educational opportunities. In this paper, the development and evaluation of a system designed to address this problem is described. The Lifelong Learning in London for All (L4All) project has investigated the concept of trails as a way of organising lifelong learning opportunities. The L4All pilot system combines a set of web services to provide the functionality needed to support this central idea. The development process was outlined, and the findings of an empirical study were used to confirm proof of concept.