Is there a trick to growing larger winter squash?
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There is, actually. It involves pruning most of the fruits off the squash vine and allowing all the growth to concentrate in just a few (i.e., quality over quantity) . Even, consistent watering is also key.
https://www.gardeningknowhow.com/edible/vegetables/squash/growing-winter-squash.htm
Miracle Grow used twice a month has been a great growth buster for my plants.
you could try putting a strand or two of knitting wool through the plant stem just before the fruit and keeping one end of the wool in a container of water nearby.It should draw the water up the wool and straight into the fruit