Most squashes are at their "driest" immediately after harvest... not in terms of their moisture content, but in their cooked consistency. At this point (provided the squash was fully ripe) the starch content is very high, and the cooked texture will resemble mashed potatoes. So if you cooked a fresh-picked squash, Casey, that was probably the reason for the dryness.
Personally, I prefer squash at this stage, when it can be used as the starch in a meal. I leave them on the vine as long as possible to preserve their starch content, and also to allow the seeds to fatten up for seed saving.
Once a squash has been separated from the vine, the starch begins the process of conversion to sugars. The squash becomes sweeter, and the consistency (when cooked) begins to soften. Some prefer their squash in this stage... and if they have always eaten winter squash after it has aged, it may be that the soft, sweet stage is all they know.
It comes down, I suppose, to personal preference. I like acorn squash when fresh-picked, and hubbards & buttercups after they have aged.
