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When your horse reaches 3 yrs old you can select which style of comps you want to specialise in: Classical or Western. You need to select Classical to enter a dressage event. You can change the style any time up till the horses 5th birthday (or anytime with the appropriate VIP perk).

You can then equip your horse with tack, and the competitions box will be displayed. Select Dressage comps and a list of those available will appear. Pick the one you fancy and press enter.