Winter Squash Puree with Roasted Garlic and Onions

This dish is nice and rich, perfect as a side dish for a mild meat like chicken. It’s very time intensive, but it’s worth it if you’ve got the time.

Roasted Garlic

3 heads garlic
3 tablespoons olive oil
salt and pepper
2 tablespoons water

Preheat oven to 400 degrees. To prepare the garlic, cut off the top third of each garlic head and discard. Stand the garlic heads upright in the center of an 8-inch square of aluminum foil. Drizzle with olive oil, season with salt and pepper, and sprinkle with the water. Loosely seal the foil closed. Place on oven rack and roast until soft and slightly caramelized, about 1 1/2 to 2 hours (I had to do mine for 2). Set aside.

Squash Puree

3 lbs winter squash such as butternut or acorn, halved lengthwise and seeded
3 tablespoons olive oil
salt and pepper
2 tablespoons butter

Lower oven temperature to 375 degrees. Place squash, cut sides up, on a baking sheet or in a glass baking dish. Sprinkle with olive oil, salt, and pepper. Place in oven and bake until the squashes are soft when poked, about 1 1/2 hours. Set aside to cool.

Caramelized Onions

3 small (I used 2 large) red onions, cut through the root end into wedges
3 tablespoons balsamic vinegar
3 tablespoons olive oil
salt and pepper

Raise oven temperature back up to 400 degrees. Toss onion wedges with the olive oil, balsamic vinegar, salt, and pepper. Pour the onions and liquid onto a baking sheet. Roast until caramelized and the edges are crisp, about 12-15 minutes (I had to do mine for about 20, adding a bit more balsamic vinegar and olive oil). Remove from oven and let cool. With small scissors, snip off the root end holding the layers together on each wedge. Set onion pieces aside.

Puree and Finish

Using a large spoon, scoop the flesh from the squash halves. Put half of the flesh in a food processor and puree until somewhat smooth. Add 2 tablespoons butter and the rest of the squash and puree until very smooth.
If you don’t like chunks of garlic (I don’t), squeeze the roasted garlic out of it’s skin and puree it in with the squash.

Melt a tablespoon of butter in a saucepan over medium heat and add the puree mixture and onions, stirring slowly to heat and incorporate all ingredients.

Serve hot.

Also good topped with blue cheese crumbles!