Thank you so much for your helpful information, Pete. Since posting my original questions, a friend informed me that the Wiscasset wharf depot did in fact have three windows facing the river. These were lower down at ground floor, likely due to the elevated position the structure enjoyed atop the wharf.
I recall that within the W.W. & F. Ry. Museum archives is a collection from the late Fourtin Powell. I remember him being a dedicated fan of the Kennebec Central Railroad and his correspondence collection bears that out. He wrote back and forth with the late "Dick" Andrews of Waterford, Maine and there were letters well illustrated with both mens artistic talents. The two had a love of sailing in common as well.
Pete, I enjoyed your mention of observing the flag to gain information on the wind. Having done a little sailing myself, I know how critical that observation can be. One can picture a Schooner Captain coming up on the docks in Randolph or Wiscasset and how surely wind and weather could make a difference.
I remain curious about night time docking, docking in snow squalls or fog and if any type of lantern might have been used, hung up or hand held during such events.
That same curiosity remains in regards to the Lakes steamers operating into Rangeley (Marbles) and on the Long Lake steam boat destinations of North Bridgton and Harrison. I'm assuming most if not all trips were run in daylight, but do not know for certain.
Again, thank you for your help.