I know at least two of you have posted recently about cooking chestnuts, so I know someone out there must know how to do this properly.
There are no longer venders selling hot roasted tiny chestnuts with the paper thin shells at 99 Ranch Supermarket on weekends. So I had to purchase regular size chestnuts.
I slit each one to let steam escape as I read about once, and baked them in the oven for 20-30 minutes. The shells were difficult to remove and it was even harder to get the papery stuff off each one. Should I have failed to slit them? Would this have kept the moisture in and made them easier to peel once I got the shells off? And how long should I bake them and at what temperature? Or is it better to cook them in a wok the way the Chinese prepare the small chestnuts with the papery shells? How long should I wok them for?
A friend was in the other room while I was thinking over and over to myself, "Never again." She came into the room and said to me something like, "Let me guess, never again on the chestnuts."
Now I want to try it again without slitting them first. But not for a while.
There are no longer venders selling hot roasted tiny chestnuts with the paper thin shells at 99 Ranch Supermarket on weekends. So I had to purchase regular size chestnuts.
I slit each one to let steam escape as I read about once, and baked them in the oven for 20-30 minutes. The shells were difficult to remove and it was even harder to get the papery stuff off each one. Should I have failed to slit them? Would this have kept the moisture in and made them easier to peel once I got the shells off? And how long should I bake them and at what temperature? Or is it better to cook them in a wok the way the Chinese prepare the small chestnuts with the papery shells? How long should I wok them for?
A friend was in the other room while I was thinking over and over to myself, "Never again." She came into the room and said to me something like, "Let me guess, never again on the chestnuts."
Now I want to try it again without slitting them first. But not for a while.

Comments
If you have a microwave, I have to say that if you can do them in the microwave (split the shell, then put them in at full strength for a minute--but only do a few at a time), you may have better luck. The ones I did in the microwave peeled with no problem.
Another possibility is boiling them. Again, slit the shell, and boil for ... hmm, I forget how long, but if you search on "processing chestnuts boiling," you should get a time amount. The thing about boiling them is that you have to keep them warm in the water or it's hard to peel them. But so long as they're warm, they slip right out of their shells. And boiled, they taste as good as roasted, and you can use them for all sorts of things (stuffings, bread, as well as eating out of hand).
You MUST slit the chestnuts or you risk having them explode (either doing cooking or when you pull them out). Most suggest the flat side, but some say X them on the rounded side. Regardless, roasting with the X side up is a must.
I've seen different times and temperatures. 425 for 15-20 mins, or 375 for 20-30 mins. So, I can't remember what I did last...another chef said 400 degrees for 15 minutes. Sounds like the middle is the best bet.
Perhaps yours were just a tough bunch? I've had it happen before (I think if they're older that can tend to happen). If picking them fresh, they're best when they're plump and not hard, unbruised, and with a shiny shell.
The one thing I'm not sure you did is mound 'em up in a towel, wrap it up and squeeze hard so you hear some crackles. Then, let 'em sit in the towel for about 5-10 mins before peeling. I think this step would've helped you a lot.
Another suggestion I just found in researching was to soak them after scoring in cool water for about 15 minutes. This same chef suggested 400 degrees for 15 minutes. I think the higher heat tends to help make the shell and skin more brittle. He also suggested the towel trick above. But, I'm definitely going to try the water trick next time I do mine.
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Best of luck on your next roasting. But please slit them to avoid a serious burn!