I love winter squash, just like Josh, and am so excited about it. Below are two recipes that I've used for the past few years. One simple, one less so.
simple maple glazed acorn squash (my own recipe):
Cut them in 1/2, scoop out seeds. Place flesh side down in shallow pan. Prick tops a couple places with a fork. Combine a couple tbs butter with 1/4 cup maple syrup. drizzle over the squash, cover them with tin foil and roast at 425 for 1/2 an hour or longer, til nice and soft. May want to rotate them.
I then serve them straight up with a little added maple syrup poured into the bowl part. Yum. Can always add cinnamon or nuts, too.
Winter squash soup with gruyere croutons.
*addendum: I roast the squash first. 425, Cut in half, covered with tin foil, drizzled with olive oil. Use a fork to prick to see how soft it is... Also, the croutons are sooo good! Don't not make them... and use gruyere. I'm all about using whatever is around... except in the case of gruyere.
Melt butter in large pot over medium heat. Add onion and garlic and sauté until tender, about 10 minutes. Add broth, all squash and herbs; bring to boil. Reduce heat, cover and simmer until squash is very tender, about 20 minutes.
Working in batches, puree soup in blender. Return soup to same pot. Stir in cream and sugar; bring to simmer. Season with salt and pepper. (Can be made 1 day ahead. Chill. Rewarm over medium heat before serving.)
Preheat broiler. Butter 1 side of each bread slice. Arrange bread, buttered side up, on baking sheet. Broil until golden, about 1 minute. Turn over. Sprinkle cheese, then thyme and sage over. Sprinkle with salt and pepper. Broil until cheese melts, about 1 minute. Ladle soup into bowls. Top each with croutons and serve.