If you look on your calender at your house, it will show that on fall and spring, there will be a horse festival (the day you can race your horses) go to theadore at the town square and he will ask you what you want to do. go to "start the race" and he will ask you if you want to perticipate. In order to participate your horse will have to be close to that ranking level. If it says you cant participate keep doing the same thing. If its your 4th time doing that and it still says you cannot participate,then you must have not had leveled up your horse with 2 hearts. You have to have 2 or more hearts in order to participate at least one of your horses.If you still don't understand, I'm not shure what you can do.I hope I helped! - Ashlie R.
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Ok, first you save your game before you enter the town square, after that you go in and see which horses win, you write it down - if you think you will forget it - and then relode the game, enter again and bet on the winning horse.
You will need to have a horse you use a lot and ride a lot and it has to have alteast 2 hearts to ride. The more hearts the most likely it is to run.