as long as your warm then you can ride everyday. the horses love the winter way more then summer cuz the codl dosent really effect them and so they get alot more frisky and want to go go go. just watch out for ice patches(if you get those) you dont need to bath your horse very often but cooling it down after every ride in the summer (right up till october) is always good, thats what i did with the horse i part borded before my triggy boo came along, i dont know how the summer is going to be with him , it will be his forst with me, but even in the fall he sweat like a pig lol, his whole body would be like 10x darker