I've received several questions about when fall squash are ready for harvest. Fall or winter squash should be harvested when fully mature which is more typically in September than August. Immature fruit have a watery flesh, don't store well and if harvested are eaten like summer squash. Not all of them will taste good when eaten immature, hubbard and golden acorn reputedly are O.K.
As fall squash matures, the flesh becomes drier and sugars develop. Both changes contribute to storing quality. Some types will store up to 3 or 4 months when harvested at the right time and stored under ideal conditions (dry and 55 degrees F). One inch of neck should be left on the fruit and it should be hard and dry when harvested.
General signs of maturity are skin that can't be easily dented with a thumbnail, color that is true to mature type, and reaching the proper number of days to harvest.
Certain types of squash have other things to look for. On acorns, the groundspot where fruit touches the ground will change from yellow to orange. Carefully turn fruit over to check being careful not to detach from the stem in case you have to roll it back to let it ripen further (photo acorn above left - still yellow: immature). On golden acorns, the groundspot doesn't show like it does on green acorns. Yellow skin should turn a deep golden yellow at maturity on these.
Butternut squash are ripe when vine growth stops and skin color changes from a light whitish tan to a deep tan (photos below - left photo immature, photo right fruit medium mature and still needs time to turn a deep tan).
Vegetable spaghetti squash are mature when they turn from a light yellow to golden yellow (photos below). Buttercup squash are ripe when dark green fruit are 5 to 6 inches across and stop growth. These are the most common varieties grown by home gardeners because their approximately 80 to 85 days to harvest makes them reliable in our climate.
Blue hubbard (blue-gray) and Boston marrow (reddish-orange) are occasionally grown. They take a full season, 110 and 120 days respectively, and are mature when vines die down.
Photo credit: Rotating acorn to check maturity, Butternut immature and medium mature, Vegetable spaghetti immature and mature - All Carl Wilson