This is the best thing I've ever done with a butternut squash. The sweetness of the squash melded perfectly with the roasted garlic. It sounds weird, I know, but if you like squash, you won't be disappointed. This recipe will serve 6 as a side dish, pretty easily.
2 or 3 lbs dry winter squash (Butternut, Blue Hubbard or Kabocha would work well. Use any dry squash, but not acorn or Delicata - they're too wet and won't caramelize enough when you roast it)
6 big cloves of garlic
1/4 c. flour
1/4 c. olive oil
Preheat oven to 325
1. Peel and gut the squash, then cut it into tiny, 1/3 inch cubes. You can be lazy and cut the cubes bigger, but the extra caramelization that happens when you cut it into teeny tiny cubes is worth every knife stroke. Trust me.
2. Peel and roughly chop the garlic. You can use more if you are trying to ward off vampires, or if you're my friend Anna. I would use more next time, for sure.
3. Place the squash, garlic, flour and salt and pepper in a mixing bowl, and stir it all together.
4. Oil the bottom and sides of a large roasting pan. The biggest you can find. Then dump the squash mixture into the pan and pour the olive oil over the top. You can use more oil if you're not watching your girlish figure. It's good with more.
5. Bake/roast for 2 + hours, until the squash is golden brown all over.
6. Serve. Don't expect leftovers, but if you can't eat it all in one sitting, it's very, very good hotted up the next day too.