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The Talmberg horse race is only held during the Talmberg Horse Race quest.

You have to ride on the horse given, no using Warhorse Jenda. The competition is really fast, but luckily, you don't have to use the road. If you get pretty good at running through the woods, you shouldn't have a problem. The shortest distance between two points is always a straight line, and the NPCs always use the curvy main roads. Just watch out for hills and tree branches, because for some reason, Henry still takes leg fall damage from two inches even though he's on a horse.