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Twice-Roasted Squash With Vanilla, Maple, and Chile

4.6

(18)

TwiceRoasted Squash With Vanilla Maple and Chile recipe
Photograph by Emma Fishman, food styling by Susie Theodorou, prop styling by Sophie Leng

The undisputed worst part of roasting squash is laboriously hacking apart a rock-hard gourd. Skip that entire process by roasting a kabocha squash whole, then tearing the cooked flesh into pieces to roast again under a fragrant and slightly spicy glaze. The result is tender squash with a sticky-sweet sheen in boats of crispy skin. If you want to work ahead, roast the whole squash a day before you need it and store it in your refrigerator; before serving, simply tear the squash, drizzle it with glaze, and pop it back into the oven for the final roast.

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What you’ll need

Recipe information

  • Yield

    8 Servings

Ingredients

2

2½–3½-lb. kabocha squash

2–3

Fresno chiles, thinly sliced

½

cup pure maple syrup

1

Tbsp. vanilla extract

Kosher salt

cup extra-virgin olive oil

3

Tbsp. toasted sesame seeds

Preparation

  1. Step 1

    Preheat oven to 425°. Poke each squash a few times with a sharp knife, then place on a foil-lined rimmed baking sheet. Roast until a fork easily pierces through skin, about 1 hour. Let sit until cool enough to handle, then cut each squash in half. Scoop out and discard seeds. Tear squash into large pieces and arrange, flesh side up, on same baking sheet.

    Step 2

    Increase oven temperature to 450°. Bring chiles, maple syrup, vanilla, and a big pinch of salt to a boil in a small saucepan; reduce heat and simmer until thickened, 8–10 minutes. Remove from heat and stir in oil.

    Step 3

    Generously season squash with salt, then spoon maple syrup mixture over each piece. Roast squash until darkened slightly and jammy in spots, 20–25 minutes.

    Step 4

    Transfer squash to a platter and sprinkle sesame seeds over.

    Do ahead: Squash can be roasted 1 day ahead. Let cool. Wrap in foil (leave whole) and chill.

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Reviews (18)

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  • Where did you do with the 1/3 cup of olive oil?

    • Lulu

    • 10/15/2022

  • Great as a side dish or as a healthyish snack. Love the vanilla note.

    • Sophy

    • Ashland, OR

    • 7/4/2022

  • I really like the flavors and the simplicity of this recipe. However, my squash dried out so badly. Rather than being soft, it broke apart in dried up chunks. I wish I could see all the reviews to determine if others had this issue and what they did.

    • LynnS

    • Oshkosh, WI

    • 2/1/2022

  • I took Angela's advice and didn’t cook it as long on the first bake which worked well.I thought the recipe called for too much vanilla. I wonder if you could use Trader Joe's chili oil and just add the maple syrup. I did think the sweet and spicy flavors worked well with the squash.

    • Sue

    • Denver

    • 1/19/2022

  • Flavors were really good, but I found that the squash cooked much faster than the time listed in the recipe. This meant my squash got really soft and it was impossible to tear the squash apart and have it sit upright to roast again as instructed. It also meant the skins were too soft to separate, but not really that great to eat with the super soft flesh and it ended up looking like kind of a mess. I would try this recipe again, but I would reduce the initial roasting time.

    • Angela Skrade

    • Minneapolis, MN

    • 12/5/2021

  • Perfection! Tasty balance of sticky sweet and spice. Texture of this particular squash is velvety and not stringy or chalky.

    • Laura Esposito

    • Nashville

    • 11/26/2021

  • Can’t access other reviews

    • Jan

    • Bellingham, WA

    • 11/23/2021