Before 1959 (and the construction of the Matterhorn), the highest point in Disneyland was Tom's Treehouse on Tom Sawyer Island. The tree itself wasn't that tall, but it sat on top of a hill and afforded adventurous guests with some very nice views.
There's the Viewliner! Unfortunately our photographer did not take any other pictures that captured the Train of Tomorrow, so this one will have to do.
I think we're looking to the north and a bit to the east here, and Frontierland was still pretty empty. It helped to give it that authentic frontier ambiance I suppose. There's an interesting detail in this pic as well!
On top of that rock stands our old pal Stormy! That's what I call him anyway. You can call him whatever you want. This proud pony wasn't there for very long. In fact I have a photo from the following year in which Stormy has been replaced with a mountain lion (here's a better shot of him).