Pilots have always worked in pilothouses. On very early steamboats, there was barely a pilothouse but a kind of a pilotstand with sunshield above. Even if you find pictures e. g. from the New Orleans with a big pilothouse it's more likely that there was no such big pilothouse, as the pictures were painted in a later time when pilothouses were common already, so the artists added the pilothouses to the boats instead of painting the boats in their original shape. Later, when the pilothouse high up on the roof came up, they had an open forward window area, even in winter times. That was required for the pilots could see and 'sense' the smell of the wind, hear the sounds of the river. Also, tha quality of glass at this times was to weak to have a clear view throug it. There were no electronic navigation systems then and all depended on keen eyes, ears and noses combined with training/experience.