We are just completing a small addition with a gambrel roof. One side of the addition has two dormer windows and one "wall dormer" which has no slope (vertical, less than 3 feet wide, located where gambrel roof joins existing house). The wall dormer is currently covered with facia board and painted to match the dormer window trim, but we think it would blend in better if shingled to match the rest of the gambrel roof. Is it possible to put asphalt shingles on this vertical surface? Thanks.
As in here where the facing gambrel's bottom rake edge meets the main house and you see the triangle of shingles? The difference I suppose is you were adding a gambrel to a standard wall, so it doesn't look normal as in the pic below.
If you do install shingles vertically make sure you at least nail them in the right place (there is sometimes a different line for steep nailing, or just make your nail placement as close a possible to being exposed when the next shingle is put on top), and it may require storm nailing (more nails). I'm pretty sure the last time I read the shingle package it also said hand seal every shingle with tar. Like that ever happens.
I agree that it generally looks hokey to have shingles where siding belongs, if that's your case.