For the Squash:
4 pounds Winter squash, cut according to the type of squash*
3 tablespoons olive oil
Freshly ground black pepper
Preheat the oven to 425°.
Place the squash on a large, rimmed baking sheet. Drizzle with olive oil and season with salt and pepper. Roast for 35-40 minutes until browned and tender.
Drizzle the agro dolce over the squash and set aside until you are ready to serve.
Preheat your broiler to HIGH. Place squash under the broiler for 1-2 minutes or until the agro dolce starts to caramelize.
Transfer to a platter and serve.
For the Agro Dolce:
2 Fresno chiles, thinly sliced
1 clove garlic, smashed
1 sprig fresh oregano
1 teaspoon fennel seeds
¾ cup sherry vinegar
¼ cup honey
½ teaspoon black pepper
½ teaspoon sea salt
Place all ingredients into a sauce pot and bring to a simmer. Cook for 8-10 minutes until reduced by about a quarter.
Notes on fall squash:
I have very specific feelings about how different type of winter squash should be cut. Seeing all squash cut the same way makes me moody. Each squash has a different set of beautiful textures and flavors and I want to honor those by not just cutting everything the same old way. Lets make all squash feel special!
Acorn: I like to follow the indentations of this squash, cutting into wedges and removing the seeds.
Delicatta: For this type of squash I like to cut it into ¼ “ thick rounds, leaving the seeds intact. They cook up extra crispy and add great texture to any dish you add them to.
Kabocha: There are two different ways that I like to break down this squash. Either way begins with cutting the squash into wedges, along the natural indentations. In some cases I stop here. Others, I like to cut each wedge into smaller triangular shapes. If the kabocha is smaller the seeds cook up beautifully in the beginning of the harvest. As the squash get bigger the seeds tend to be very very chewy.
Butternut: I tend to use butternut for soups, purees, mashes and the like. In that case, I peel it and cut into 1-2” chunks. For roasting, I prefer to peel and cut into half moons as it can feel a bit water and stringy to me when in big chunks.
Pumpkin: Here I like to go with the same technique as kabocha. If the skin feels thick I like to peel it on a pumpkin because I find it far more bitter than kabocha skin.