How do I know if Winter Squash is ready?

Los Alamos, NM(Zone 5a)

I know this is too early, but I want to be prepared this fall when it is time to harvest. I have planted butternut, kabocha, chioggia di marina, triamble and a couple of French pumpkins that Amy Goldman's book on squashes says are out of this world. We love winter squash, but I often have trouble telling if they are ready. I live at high altitude ( 7,300 ft.) but we do get winter squashes to mature. Summers have many days in the low nineties but rarely does it reach 100, here.
The question is how do you know when winter squashes are ready? I bring in my butternuts at the end of the season -- just before the first frost. Sometimes they don't get tender even if I cook them for a long time -- baking or steaming. I have noticed that if I wait a month or so, they are fine. Is this normal?
In the past I have planted buttercup squashes and acorn squashes. The buttercups were ready early -- or so I thought, but they were dry and tasted like paste or something. They were orange and sweet and not tough inside, but the meat was dry no matter how long I cooked it.
With acorn squash I have picked them when the stem snapped easily -- which is what I have heard is the way to tell when they are ready. They turned out to be very difficult to soften in the oven or by steaming -- which works fine on the ones from the store. Am I picking them too early or too late? My growing season is basically May 20 - Oct. 15. The squashes look great but they don't always taste great.
Any hints?

Augusta, GA(Zone 8a)

Winter squash, when used as winter squash (some can be used as immature summer squash) need get to hard skin stage. Personnaly I pick them as the vines fail or just before the first frost whichever comes first. They need a couple of weeks of curing in a cool dry enviroment before they reach thier best flavor.

Spencer, TN

with all of them we usually just leave them till the vines die, get them up before it frosts hard enough to damage them. never tried eating them right away, probably because about that time we're swamped with green tomatoes, peppers and all kinds of stuff.

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