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Preheat oven to 425F.
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Toss butternut squash with 1 tablespoon of the olive oil. Spread into a single layer on a sheet tray. Bake until squash is tender and starting to brown, 35 to 40 minutes. (Squash can be roasted up to 5 days ahead and kept refrigerated. Rewarm before serving.)
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Place the spinach in a large bowl and set aside. In a small skillet, heat the remaining 2 tablespoons of olive oil until just warm. Stir in garlic, remove from heat, and allow to sit until ready to use.
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Place the orzo in a pot and cover with at least 2 inches of water. Bring to a boil, reduce to a simmer, and cook until tender but not mushy, 8 to 9 minutes. Drain and immediately pour the hot orzo on top of the spinach. Let sit for a few minutes to slightly wilt spinach.
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Add butternut squash to the pasta, along with the blue cheese and Garlic olive oil. Toss until well combined and serve warm.