Some more painting snippets I've thought of.
'At the sign of the Prancing Pony'
Quote:
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Above the arch there was a lamp, and beneath it swung a large signboard: a fat white pony reared up on its hind legs. Over the door was painted in white letters: THE PRANCING PONY by BARLIMAN BUTTERBUR.
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So Bree at least has painted pub signs, and I strongly suspect that The Green Dragon and other Shire pubs had similar.
As Mith says heraldic art is often mentioned, eg the devices of the Noldorian princes in the First Age. But there's also the use of more representational devices, like the white horses painted on the shields of the Rohirrim. Another area is that of flags and banners. We are told that Aragorn's standard was embroidered by Arwen, but as far as I'm aware embroidered battle flags are quite rare in our reality, more often they were painted. So Rohan's horse, Dol Amroth's swan and Harad's serpent may well have been painted.