I think "circling the train" is more witty; it paints a great picture of a stereotypical American wild-west film, with American Indians circling a train whilst shooting rifles in a haphazard manner whilst shouting and yelping.

Or perhaps bandits doing the same thing.

In any case, a large collection of bespectacled Microsoft employees circling a train on horses whilst still wearing 1980s software developer outfits (shirts with pinstripes in them but white collars, high-waisted ironed trousers with a slim gold belt buckle, and big glasses, and a bushy moustache) in all the dirt would be witty, whilst dragging green-screen CRTs and big 5.25" floppy discs in their saddle bags with great difficulty.

I know, I know, this is terribly stereotypical but I think it would make for a great film in the style of Mel Brooks; you can contact me if you want obscure and off-the-wall film settings like this...