Winter Squash Pasta with Chile & Toasted Garlic
One of the more wonderful parts of squash is its ability to turn into utter mush with little to no effort. Impossibly hard when raw, it becomes effortlessly soft with just a bit of heat and time. No blender or food processor required. Magical. Though I’m not usually a fan of squash, I make an exception here because it turns into such a gorgeous sauce with which to coat little pieces of pasta that it would be a shame not to take advantage. While the squash will very clearly start to fall apart as it cooks, it’ll still rely on the addition of (quite a bit of) pasta water to turn it into a sauce loose enough to coat, so be prepared to add more water than you’d expect. While it can be made a little fancier with a dollop of burrata or ricotta or a handful of toasted nuts, feel free to resist: It’s tough to beat the delight of something so fabulous made with so few ingredients.
2 tablespoons olive oil
4 tablespoons unsalted butter(or more olive oil)
6–8 garlic cloves, thinly sliced or chopped
1 teaspoon crushed red pepper flakes, plus more
A few leaves of sage, thyme, rosemary, or oregano (optional)
Kosher salt
Freshly ground black pepper
11 small winter squash, such as kabocha, acorn, or butternut, peeled, seeded, and chopped (about 2 cups/12 ounces of cut-up squash)
12–16 ounces dried pasta, smaller, tube shapes preferred
1 teaspoon sherry vinegar or white wine vinegar, plus more
Parmesan or pecorino cheese, for grating, or ricotta or burrata, for dolloping
Heat the butter in a large, heavy-bottomed pot (or a large skillet) over medium heat. Let it melt, then sizzle, until it’s all foamy and browned, 3–4 minutes. Add the olive oil, then add the garlic, red pepper flakes, plus
any herbs. Cook, stirring, until the garlic is nicely toasted, browned, and crisped, 3–4 minutes. Using a spoon, transfer all the garlic and about half the fat in the skillet to a small bowl; set aside.
With the heat still on medium, add the squash to the pot and season with salt and pepper. Cook, stirring occasionally, until the squash is totally softened and tender, while also nicely 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.
Meanwhile, bring a large pot of salted water to a boil. Cook your pasta until it’s al dente (really al dente—you’ll finish cooking the pasta in the squash sauce). Save 2 cups of pasta water, then drain the pasta. Once the squash is so soft you can easily smush it, add the pasta and 1 cup of pasta water. Cook, stirring constantly, until the squash has melted into a thick puree, starting to coat the pasta. Add more pasta water, ¼ cup at a time, until
it’s decidedly sauce-like and the pasta is fully cooked, a few minutes.
Add the 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). Regardless, end with a spoonful of the crispy garlic chile oil and another grind of pepper.

Something from Nothing by Alison Roman
Something from Nothing Copyright © 2025 by Alison Roman. Photographs copyright © 2025 by Chris Bernabeo. Published by Clarkson Potter, an imprint of the Crown Publishing Group, a division of Penguin Random House LLC.
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