Ideally, when roasting beets, the skins should just come right off once they're done and cool. I don't seem to be good at this, though: sometimes they're great, and sometimes the skins are pretty clingy. What should I do to guarantee easy peeling?
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Are you roasting them uncovered in the oven? I always wrap them individually in aluminium foil before roasting and have no problems removing the skin later. – Stefano Mar 08 '13 at 16:19
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@Stefano That generally seems to help some (cooks them faster, too) but sometimes I still have trouble. – Cascabel Mar 08 '13 at 17:15
2 Answers
The trick that works for me consistently is to put the beets in a sealed container while still hot and let them cool down that way, they continue to cook a bit and the steam from them keeps the skins loose. Also, peel them while they are still warm, if they cool too much the skins may adhere again.

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yes, I agree letting them steam a bit AFTER baking. Baking uncovered concentrates flavor, texture – Pat Sommer Mar 08 '13 at 17:12
Blanch them first to remove the skin, then roast them. This method works for tomatoes as well.
Here's an example from ForkBytes
Blockquote Bring a pot of water to a boil. Add the beets and blanch briefly, until skins are loose, 3 to 5 minutes. Remove the beets and immediately plunge them into a bowl of ice water. Peel and cut into bite-sized pieces.
Obviously, you don't have to cut into bite-sized (I recommend not, to keep them from bleeding) and can proceed with your usual roasting method.
Some pro recipes just say cool them slightly at the end of the roast and peel. Again, this keeps the bleeding to minimum. So the above answer is assuming you want the easiest peel.

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Will covering while roasting then be sufficient to avoid drying out the outside of the beets too much? – Cascabel Mar 08 '13 at 17:34
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@Jefromi you're right, removing the skin will slightly increase bleeding, but covering should keep them moist enough. Though not covering will result in more flavour albeit less moist. The idea is to keep the bleeding to minimum. – MandoMando Mar 08 '13 at 17:56