When starting this site I organized pictures along “walks”, “rambles” or “strolls”: roughly the path I’d walk while taking the pictures. Increasingly I tended to organize pictures of particular sights as sub-galleries in these “walks”.
I now find there are too many of them, they also cross, overlap, some pictures I have moved to other categories. It is becoming a mess. So I first group these virtual routes under one heading, then I’ll take many of the constituting pictures to other galleries. The ones remaining will probably be organized as “general views”, maybe organized along major districts. I start a sub-gallery "dump": pictures of a general nature, taken all over town. I sometimes know where I took them, but for, for instance, pictures of some kids that is not important.
For people who are used to navigating to a particular walk it will be rough, but for most it will be much easier to find a particular image. And there is always google, I often find my pictures using a subject and dosseman as search terms.