Winter squash has a funny way of making gardeners second-guess themselves. One week the vines look like they could drink an entire bathtub, and the next week the leaves start yellowing while those hefty squash sit there looking suspiciously finished. The right time to stop watering winter squash generally comes when the fruit approaches full maturity, but that does not mean gardeners should suddenly abandon the hose several weeks before harvest.
The goal involves gradually reducing water as the squash ripens, rather than forcing the plant through an abrupt drought. Less water late in the season can help reduce fruit rot, especially when the squash sits on damp soil, while keeping the soil reasonably moist until the fruit finishes prevents unnecessary plant stress. The trick comes down to watching the fruit, the vine, the soil, and the forecast instead of following a rigid calendar.