Techniques that support trail-based exploration by a user of a repository of documents are described herein. In one embodiment, trail definition data that specifies a trail is received. The trail includes an ordered series of waypoints including a trailhead, intermediate waypoints, and one or more trailends. In some embodiments, deadends may also be defined in the trial. A particular waypoint in the ordered series of waypoints is established as a current waypoint. Search terms can be received from a user to cause a search to be performed. It is then determined whether the search satisfies matching criteria associated with a waypoint that immediately follows the current waypoint in the ordered series of waypoints. If so, the user advances to the next waypoint. Otherwise, the user remains at the current waypoint. Finally, if a trailend is reached, then an action such as rewarding the user in some way may be performed.