2 tablespoons butter, plus more for baking sheet
2 medium acorn squash
2 tablespoons light-brown sugar
Coarse salt and ground pepper
Preheat oven to 425 degrees. Generously butter a rimmed baking sheet.
Halve 2 medium acorn squash (about 1 1/2 pounds each) crosswise. Scoop out seeds; discard. Slice a small piece off bottom of each squash half just enough to level.
Set squash halves, scooped sides down, on prepared sheet.
Bake until golden, 20 to 25 minutes. Turn squash; prick insides all over with a fork. Divide 2 tablespoons butter and 2 tablespoons light-brown sugar among halves; season with coarse salt and ground pepper. Continue to bake until flesh is easily pierced with the tip of a paring knife, 25 to 30 minutes. Serve warm.
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