Try starting with an actual barred window image. I made this in about 10 minutes in Gimp, starting with this image
, found by doing a Google image search for "barred window" (no quotes, large images only).
The fonts are Chalkduster and Impact. The original image colors are toned down by overlaying the original image on a black and white version of itself, then making the color layer fairly transparent. The "B.A.R Brewing" text has a light drop shadow. The "101" text is underneath the color image layer and has the cloud filter and a slight blur applied.
It's rough. The window/text are not quite centered on the logo, and the "B.A.R." text would probably look better on an arc. Ideally, the original image would have a little more room at the top for the text, as well. However, it took only a few minutes to create what I think is a rather striking effect using some of the more powerful features of Gimp - layers, transparency, filters, etc.
If you think that Gimp should be able to create a particular effect, Google it. Someone else has likely made a tutorial for it. Also, I find it difficult to draw anything more complex than simple shapes from scratch, particularly when attempting photo-realism. It's much easier to start with an existing image or image fragment than to create a completely new, complex design.
EDIT: Oops...it should be "106." But you get the idea.