A brief follow-up to yesterday's post: I later noticed that in this drawing Sutherland may have included the "treacherous pathway which leads up to the craggy outcropping of black rock". It's marked above in red. The portion at the bottom especially appears to be a path, marked by Sutherland with horizontal lines, which curve behind the rocks with the stump. Past these rocks it may then continue up the cliffside to the top. On the other hand, the treacherous pathway is supposed to lead to a cave opening to the first level of the dungeon rather than the watch tower. Perhaps the cave is right behind the rocks with the stump.
By the way, the watch tower is not detailed in the module, but attempts have been made to flesh it out, for example the one here on Dragonsfoot by Shadowshack.
Update: The crevasse to the right might be another location for the entrance cave. I've circled this on the picture.
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