Should I pull shoes in the winter?

My first question back to you is, “What is the horse going to be doing?”.

If turn out in the slop is your answer, then I would pull the shoes. Thrown shoes suck the fun out of everything, no shoes on purpose is much better than no shoes by accident. In the north, the snow and ice building up in their shod hooves can be dangerous. With unpredictable weather, sometimes we can’t even get to your horse in a strictly scheduled manner, and that is much less important for an un-shod horse.

If you have a horse in work and maintained indoors, pulling the shoes can cause problems leading to delays later. I don’t think they “need a rest” from shoes. A well shod horse has much better support.