What is the best way to "over winter" containers I use for annuals?
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Nah not really. Just stack and store. I've left some of mine with soil in. I keep a huge container w good potting soil. The following spring I dump them all into that with some fresh potting soil and compost and mix it all together before refilling. If you had some weird issues with a particular pot you could bleach it real good. I've just never found that necessary.
Just store them, but when spring comes, I would clean them with some bleach and water, because I'm sure some type of insect will make a home of them during the cold months.
I too had a LARGE closed tupper ware storage container that I kept outside. I emptied my used container soil into along with fresh soil and fertilizer and repurposed for new plantings. In the summer or early spring the closed container reached high temps and killed most harmful bacteria leaving almost sterile soil.
I left my plastic made to look like Terracotta outside withe the soil and just refreshed them like the other person suggested. But my beautiful clay pots I kept in garage and emptied. I wasn't going to chance it with the weather we get. I saw that you are in Canada, I would probably empty them all and if you have a basement store them there since the temperature remains stable if not the in garage by an inside wall to keep them in a stable temperature I would consider covering with an old blanket. Plastic cracks if too cold and I wouldn't trust terracotta because clay will crack as well.