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.
All products featured on Bon Appétit are independently selected by our editors. However, when you buy something through the retail links below, we earn an affiliate commission.
2½–3½-lb. kabocha squash
Fresno chiles, thinly sliced
cup pure maple syrup
Tbsp. vanilla extract
cup extra-virgin olive oil
Tbsp. toasted sesame seeds
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.
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.
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.
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.