Roasted Winter Squash With Citrus Chile Crisp
Updated Nov. 18, 2025

- Total Time
- 50 minutes
- Prep Time
- 5 minutes
- Cook Time
- 45 minutes
- Rating
- Comments
- Read comments
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Ingredients
- 4pounds winter squash, such as butternut, honey nut, kabocha or red kuri
- ¾cup extra-virgin olive oil
- Salt and freshly ground black pepper
- 2medium shallots, thinly sliced into rings
- 4large garlic cloves, thinly sliced
- 2tablespoons toasted sesame seeds
- 2teaspoons hot smoked paprika
- ½teaspoon crushed red pepper
- 1lemon
- 1small orange
- 2teaspoons honey
- 2cups full-fat Greek yogurt
Preparation
- Step 1
Adjust oven rack to center position and heat oven to 425 degrees. Cut each squash in half through the root end, then use a spoon to scoop out the seeds. Cut each half into 2-inch-thick wedges.
- Step 2
Spread out the squash on a large rimmed baking sheet and drizzle with ¼ cup of oil. Season with salt and pepper and toss until well coated. Roast, flipping once, until golden brown and very tender, 25 to 30 minutes.
- Step 3
Meanwhile, combine the shallots, garlic and remaining ½ cup olive oil in a small saucepan or skillet over medium heat. Cook, stirring often, until the shallots begin to shrivel, crisp and turn golden brown, 4 to 6 minutes. Immediately remove from heat and sprinkle in the sesame seeds, paprika, crushed red pepper and ½ teaspoon salt. Let cool for 10 minutes.
- Step 4
Using a microplane, zest the entire lemon and half the orange directly into the chile crisp, then stir in the honey. (The chile crisp can be made 5 days ahead without the citrus zest; cover and chill. Bring to room temperature and stir in the zest just before serving.)
- Step 5
Cut the lemon and orange in halves and squeeze the juices into a medium bowl. Add the yogurt, season generously with salt and stir until smooth.
- Step 6
Spread the yogurt on a large platter, arrange the squash on top and drizzle with the chile crisp (or serve it on the side).
Private Notes
Comments
Top w/ pomegranate seeds and toasted pine nuts
Some squash peels, like honeynut or delicata, are quite edible. Others, like pumpkin, are unpleasantly thick and fibrous. For a pumpkin or butternut, I might peel before serving, but probably ot before roasting.
Don’t you need to peel the squash? If not, are the shells edible or do you eat the the rest and leave the shell on the plate?
Made as written with delicata squash. Tasty and a nice foil to a richer side like risotto or mac and cheese. Yogurt felt too plain, however -- maybe some herbs would liven it up?
I think next time I will reduce the oil quantity before adding the spices, as I found the final dish too oily. Otherwise fun and delicious.
The squash is still roasting, so can't comment on the dish as a whole, but the chili crisp is so easy easy to make, and so delicious! It's the bomb. That is all.
