Riiight, urban druid! <Smacks forehead> What was I thinking. I'm thinknig he'd spend a lot of time near the water's edge of Crater Lake. There is the Lake Park near the Old Orphanage or we could have him start on Fish Street, taking in the sites and sounds. If you want o be a bit more morbid, he could be in the Graveyard making sure all the tenants are content.
Let's go with Lake Park. I'm thinking he is a true child of the city--an orphan who might well have resided at the Old Orphanage at some time and so this area is as close to him as it gets for him.