A lot of the that has to with the game itself. But the excellent people on this forum have earned just as much praise. Unfortunately, I am more of an avid lurker than a steady contributor, always ready to read the most recent discussion on lore and house rules or pick up excellent fan supplements like Mythic Battles, but not as willing to jump into the discussion or bring up the effort to create supplements of my own. There is, however, one way in which I might be able to contribute and my guess is there might be others who could to that too.
I have always liked drawing and since I got an IPad, it has become my favourite medium, because it allowed me to explore new techniques and even make some first steps in digital painting or colouring. My most recent experiments have been inspired by Jon's fabulous art for TOR. His paintings have a very down-to-earth feeling that stands in contrast to other, more epic Middle-Earth artwork. The way I see Wilderland has been strongly informed by all the illustrations of TOR and Hobbit Tales.
This made me think that we could have an 'art thread', in which we collect our small experiments and ideas that the larger community might enjoy.
So, for the first post, let me present some characters. First, the Witch of Mirkwood:

My first piece of work was the Witch of Mirkwood, because she is bound to become one of the major antagonist in my campaign. I drew and coloured her in ArtStudio (an app full of features and options, but with a rather slow UI).
[HERE THERE BE MINOR SPOILERS] Watching some video tutorials I encountered the idea of repeating elements to give one's image a certain consistency. So when I thought about the witch I considered her background. As she hails from Umbar, I wanted to use some imagery associated with the depths of the sea. So I thought about the head of her staff and came up with the idea of making it a black squid. The black strands of hair resemble the squid's tentacles, giving the witch a more unwholesome appearance. The squid's eye, a black orb vaguely alluding to the lidless eye, can be also be found in the black jewel on the ring, which is again mirrored in the witch's black pupils. And, of course the crown of spikes has its counterpart in the girdle. I still have some problems with drawing hands, but after some attempts I just got lucky.
So, on to the next character: The Gibbet King

In my campaign, the Gibbet King plays only a minor role and is basically a wight of great power. The imagery, however, is not changed by this. This is another image I drew and coloured in ArtStudio. Here you can see more clearly that hands and feet are still a problem for me. The folds of the gown are also far from perfect. The only thing I am really happy with in this picture is the lighting. My players found the image creepy enough to stay as far away from 'that thing' as possible.
And now to my last character: Valderic of the Erringmen

My players have a somewhat ambivalent relationship with Valderic. They have saved his life and he has helped them on an expedition deep into the Gladden Fields, but they have also had more than one confrontation over the right course of action. Valderic's pride and his interest in forbidden knowledge is something that makes my players rather uncomfortable. He, on the other hands, detests their righteous attitude, claiming that it is easy to do cling to moral absolutes when you are not looking at the larger picture.
Even though I find this image lacks some of the character of the other two I am very happy with it for two reasons.
1) It was painted in ProCreate (now my one and only drawing app because of its responsiveness) and was my first attempt at a new technique I learned from a video tutorial.
2) It was finished within two days using one single brush 90 percent of the time. The other images took me weeks of experimenting with brushes, layers, effects, etc. I really feel like I have been making progress here.
So, what have been your art experiments for TOR? And I don't want this thread to be only about characters. Have you created crests, ornaments, or maps? Maybe some drawings of weapons? If so, show them. This is what the thread is for.