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Alison Roman’s Winter Squash Pasta with Chile & Toasted Garlic  

11/07/25

Alison Roman’s Winter Squash Pasta with Chile & Toasted Garlic

Serves 4

Ingredients

  • 4 tbsp unsalted butter (or more olive oil)
  • 2 tbsp olive oil
  • 6–8 garlic cloves, thinly sliced or chopped
  • 1 tsp crushed red pepper flakes, plus more
  • A few leaves of sage, thyme, rosemary, or oregano (optional)
  • Kosher salt
  • Freshly ground black pepper
  • 1 small winter squash, i.e. kabocha, acorn, or butternut, peeled, seeded, and chopped (about 2 c/12 oz of cut-up squash)
  • 12–16 oz dried pasta, smaller, tube shapes preferred
  • 1 tsp sherry vinegar or white wine vinegar, plus more
  • Parmesan or pecorino cheese, for grating, or ricotta or burrata, for dolloping

NOTE: Your choice of cheese will come down to personal preference.

Instructions

  • Heat butter in large, heavy-bottomed pot (or a large skillet) over medium heat. Let it melt, sizzle, until it’s foamy and browned, 3–4 min. Add olive oil, garlic, red pepper flakes, plus any herbs. Cook, stirring, until garlic is toasted, browned, and crisped, 3–4 minutes. Using a spoon, transfer garlic and about half the fat in the skillet to a small bowl; set aside.
  • With heat still on medium, add squash to pot and season with salt and pepper. Cook, stirring occasionally, until squash is softened and tender, and browned and caramelized in spots, 12–15 minutes. You should be able to easily smash a piece of squash with a spoon; if it’s still a little hard, keep cooking.
  • Boil a large pot of salted water. Cook pasta until it’s al dente (really al dente—you’ll finish cooking the pasta in the squash sauce). Save 2 c of pasta water, then drain pasta. Once the squash is so soft you can easily smush it, add pasta and 1 c of pasta water. Cook, stirring constantly, until squash has melted into a thick puree, starting to coat the pasta. Add more pasta water, ¼ cup at a time, until it’s sauce-like and pasta is fully cooked, a few minutes.
  • Add vinegar and season the pasta with more salt, pepper, vinegar, and red pepper flakes if you like. Grate the Parmesan (if using) directly onto the pasta, and divide among bowls or plates. Grate a bit more cheese or dollop your soft, creamy cheese on top (if using). End with a spoonful of the crispy garlic chile oil and another grind of pepper.

 

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