Getting Unstuck

I admit it. I got really, really stuck - to the point where I'd stopped working on this for a couple of months (!!) - all because of the beginning of the second sentence to the right. I so wanted to show my characters seeing Castlebar from the hill. I know what road they were riding, and I followed that road on google streetview a million times trying to find a place where the town might've been seen from. 

Okay, there is the matter of 120 years having passed, but basic topography must remain, and given the town today being far bigger, it should've been even more visible. Are there trees or buildings in the way? Or....?  

Eventually I hope to go to Ireland and follow the route and see for myself, but in the meantime I went about it a different way; this is after all only a draft and will all be reviewed later. 

Another issue being the colours of the buildings. I've seen good old photos to base these panels on, but of course all in black and white. Guessing at plausible colours for the time being.