Winter squash is kind of a bitch. It has the whole supertough skin, which requires some serious cleaving action to deal with effectively. Then, once you've gotten the thing split/peeled/seeded of all its stringy little bits, it takes an hour to cook. It's hard to eat squash on a weeknight.
Of course, on the weekend you have hours of laying around available. You can whack that squash in half and leave it in the oven while you go play video games. Then you can either use the flesh right away or stick it in the refrigerator for later. It is an excellent idea.
I like acorn squash, so that's what I'm using.
Baking a winter squash:
Preheat the oven to about 350F. Get out a good knife and whack the squash in half through the stem end. This is not anywhere near as hard with a little acorn squash as it is with, say, a butternut. Butternut squash is awkwardly shaped and can grow into some totally appalling coils if you let it. You'd have to cut a squash like that into lots of big chunks, then halve all of them. Acorn squash, in contrast, is little and squat and only requires one cut. Once it's halved, scoop out all the seeds and chuck them.
If you were going to boil your squash, you'd have to peel each half and cut them into reasonable chunks. So instead of doing that, get out a little baking pan. Stick the squash halves in, cut side up. Add a bit of olive oil or butter to each half. Then chop a quarter of a storage onion into medium chunks and divide them into the two halves. This is clearly for savory squash; if you're going to use your squash for pie or something, don't add any onion. Also make sure to use a flavorless oil instead of olive oil.
Stick it all in the oven and bake. If you want, you can add some water in the bottom of your baking pan; this will steam the top flesh faster and keep the heat uniform at the bottom. It works fine to bake squash without any water, though.
Check back in about a half hour or 45 minutes. This time is going to depend pretty heavily on the size of your squash. If the flesh is tender and there are lots of goldeny brown crusty bits on top, you're done. If not, rotate the pan and leave it another 15 minutes, or however long it takes.
When things are done, pull them out of the oven and let them cool for a couple minutes. Then get a fork and scrape as much flesh as possible out of each piece of squash. I find this easiest when actually holding the squash; make sure to keep your oven mitts on if you do this, since the squash will be pretty dang hot.
Now you have a bowl of squash puree. Squash!
What will you do with it?
*Make delicious squash-onion-sage and marjoram soup
*or squash/black bean/cayenne soup
*or use it instead of pumpkin/sweet potato in a pie of some sort
*or find a pumpkin/squash bread recipe and do that
*or stick it on a plate and eat it with gravy/chunk of meat/seared tempeh/something, plus a green salad
Squash and black bean quesadillas
refried beans (or whole cooked, whatever)
any other vegetables you want
cheese or no cheese
These are super easy.
Get out a tortilla. Spread squash puree down one half, and refried beans down the other. I usually cook a bunch of onions and garlic and hot pepper into my beans, so I don't really need to add any more vegetables. If you have just plain beans though, you can add lots of things: caramelized onions, fresh green onion, cooked corn, hot pepper rings, whatever. Add these to the bean half. If you want cheese, slice it thinly and put a layer of it over the beans as well. Most hard cheeses will work ok here; I had sharp white cheddar. Once you've added everything you want, fold the squash half of the tortilla onto everything else. The result will probably be very thick and exciting.
Prep as many tortillas as you want, then cook, two at a time, in a frying pan over medium heat. Since these are pretty thick, it can take five or so minutes to brown the first side. Check then out every once in a while. When the first sides are browned, flip the quesadillas carefully. It's easiest to just lift one up with a spatula, put your hand on top, flip the entire construction, and lay it back in the pan. Or you can just use the spatula and work quickly.
When both sides are browned, eat with salsa or sour cream or yogurt cheese or guacamole. Or plain.
You can also make these with leftover mashed sweet potato instead of squash! YES.