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Any tips on when to harvest these two?

  Ive massive plants now, but not sure how you determine when to start harvesting.

they are always at their best when a frost has helped them on their way so you might have to wait until the October full moon - the first frosts often come then

Calendula, Ricado's right â€" October earliest, really. Then keep cutting the smaller leaves throughout the winter. The big ones will get tough. In March, they do these leetle broccoli-like buds which are also pretty tasty.
My winter veg are at all different stages now - some are huge, and some are still very small. All due to being gifted with brassicas at different times of the summer...

Just to put a little weeny spanner in the works  ;)  I harvest as soon as the plants have 6 or so true leaves, just nipping a couple from each plant as and when I want them.  I love my greens, and find that in the autumn and winter, I have masses as I grow chards, kales, spinach, sprouts, cabbage, brocs, chinese greens, etc, so I don't bother to wait from the frost.  On my plot, I don't see frosts until way into January anyhow as we are very sheltered and warm.  The lovely fresh new leaves from the middle are great in salads or steamed for just the briefest time, the bigger tough leaves I adore shredded and braised or again steamed for longer, great with Oyster sauce!  :P

I think I'm I'm a pre-frost man as well (but it is our first year): we ate our first kale 2 months ago!

I'd grown far too many seedlings for the space they were going in to and also had let them go a bit far before transplanting (about a foot high) so we ate the thinnings we didn't give away and jolly nice they were too - hardly needed cooking!

Have to admit only picked the next lot this week :)

PS How do these smiley things work?

My feeling is, if at the end of the day they're edible now, eat 'em!  ;D My problem is with kale is that I never seem to get my act together early - mine are quite petite right now. I ordered plugs from Marshalls and they just arrived a week or two ago. Little midgets.
However, I've been eating some chard I grew from seed and it is delish. That and broccoli raab. Heaven!

I've started picking my Kale now and have had two large batches since 25th August from only 6-8 plants. The rain we had spured them on big time.