Summer squash can be eaten at any size, but winter squash are more particular. Harvest winter squash when the rind is deeply colored and thick enough that you can't break it with your fingernail. Make sure you harvest before the first frost, or when you've had more than a week of weather below 50 F (10 C).
How do you know when a squash is ready to be picked?
Press your fingernail through the flesh. If you have to work at it, the squash is ripe; if it's very easy to pierce, the squash is immature. The skin should be full (non-glossy), firm, and rich in color without blemishes or cracks or soft spots. The stem should be dry and firm.
What month do you harvest squash?
Unlike summer squash that is harvested as the squash ripens throughout the season, a crop of winter squash generally ripens and is ready for harvest all at once – usually in late summer or before the first frost in autumn.