Line a baking sheet with parchment paper. Toss the cubed butternut squash with olive oil, salt, and pepper until evenly coated.
Spread the squash in a single layer on the prepared baking sheet and roast for 25-30 minutes, stirring halfway through, until tender and golden.
While the squash roasts, bring a large pot of salted water to a boil. Cook the pasta according to package instructions until al dente.
In a skillet, heat a bit of olive oil over medium heat. Add the fresh sage leaves and sauté until crispy, about 2 minutes.
Reserve a bit of pasta water (about half a cup) before draining the pasta. In a large pot, combine the roasted squash, sautéed sage, and drained pasta. Toss gently, adding reserved pasta water as needed to loosen.
Serve topped with freshly grated Parmesan cheese and an additional drizzle of olive oil if desired.
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Notes
Store leftovers in an airtight container in the refrigerator for up to 3 days.