If you have a microwave, microwave the squash for a minute each, to make it easier to cut. Then stabilize the squash on a cutting board as best you can, stem end down if the stem is short enough, otherwise on the side. Using a sharp, sturdy chef’s knife, carefully cut the acorn squash in half, from tip to stem. If on its side, the squash can rock back and forth, so take care as you are cutting it.
Use a sturdy metal spoon to scrape out the seeds and stringy bits inside each squash half, until the inside is smooth.
Take a sharp paring knife and score the insides of the acorn squash halves in a cross-hatch pattern, about a half-inch deep cuts.
Place the squash halves cut side up in a roasting pan. Pour 1/4 inch of water over the bottom of the pan so that the squash doesn’t burn or get dried out in the oven.
Add the butter, salt, brown sugar, and maple syrup:
Rub 1/2 tablespoon butter into the insides of each half. Sprinkle with a little salt if you are using unsalted butter.
Crumble 1 tablespoon brown sugar into the center of each half and drizzle with 1 teaspoon maple syrup.
Bake at 400°F for about 1 hour to 1 hour and 15 minutes, until the tops of the squash halves are nicely browned and the squash flesh is very soft and cooked through.
It’s hard to overcook squash, it just gets better with more caramelization. Don’t undercook it.
Remove from the oven, cool a bit, and serve:
When done, remove the squash halves from the oven. Spoon any buttery sugar sauce that has not already been absorbed by the squash over the exposed areas. Let cool for a bit before serving.
Make Ahead Tips for Acorn Squash
Bake the full squash recipe up to 2 days ahead of time. Wrap each piece individually in foil and store in the refrigerator. Reheat in the foil at 400°F until just heated through. The foil will help the squash retain its moisture while reheating.
Try This Method With Other Winter Squash
Other winter squashes would work with this method, too. Try these varieties of squash baked in the same way (you may need to quarter large squash).