OpenMTBmap of Gibraltar
This map of Gibraltar is based on data from the OpenStreetMap Project. The Openmtb map focusses -as its names suggests- mainly on mountain bike but also on hiking trails. Autorouting is possible with a preference for trails and offroad ways. The focus of this map is on outdoor related features and ways, however the maps do not feature contour lines but they are available separately. The maps are updated weekly and come with a Mapsource installer but unfortunately not with a RoadTrip installer.
OpenStreetMap works that way, that everybody can upload their GPS tracks from which maps from all over the world are being created. This means that the quality of the map depends on the tracks uploaded by the users (you're welcome to contribute to the project by uploading your tracks as well) and therefore the quality differs greatly from country to country, region to region and city to city. As there are continuously new tracks being contributed the maps are getting better and better every day, so if a map of a region is not as detailed as you had expected either join the community and help by contributing and/or come back in a few weeks or months and you will most likely find a better map with more data and information than there was before.