The carved pipe looks like a nice circa 1890s meerschaum with an amber type stem and a sterling band. Pretty sweet! The bulldog looks like it might be from slightly later. Maybe 1910. Could be a bit earlier or later. Also very nice!
I can't see the calabash very well. If it has an amber stem as well I'd say it's from the same time period.
The brands don't mean anything to me. But there were many, many makers and sellers back then.