The trickiest thing about squash, hands down, is cutting it in half. Sometimes the store sells them already split, which is kind of nice. But when I got the above squash from my friend's garden, it was whole. Which turned out okay in the end, as I managed (with a bit of strength, a sharp knife, and the powers of leverage) to get it cut into two pieces. From then, it's easy enough - but I do always forget what temperature to roast it at, and for how long. For that, I turned to the trusty How to Cook Everything by Mark Bittman. I took the above picture just before the squash went into the oven - lining your pan in tin foil is a good idea, as things can get a little sticky.
Here are the details:
Roasting Hard-to-Peel Winter Squash
1 acorn or other winter squash, washed
2 Tbsp butter or olive oil, more or less
salt and freshly ground pepper, to taste
maple syrup or brown sugar
Preheat the oven to 400. Cut the squash in half and scrape out the strings and seeds. In each half, put some butter, salt, pepper and sweetener (I used maple syrup). Place in a baking dish, (I used my 8x8 pyrex, lined with tin foil) cut side up, and bake until tender, about 1 hour. Serve.
(You can scoop the squash and it's flavorings into a serving bowl and mash it all together, or simply serve each individual half a squash, for scooping out at the table.)