Stuffed Winter Squash with Chili Oil

Happy New Year! Lets get cooking! Fill up colorful, sweet winter squash with my savory mix of greens, ricotta, and spices. Garnish with chili oil as a flavor boost.

If you garden in Alaska, you may have a store of blanched Swiss chard and kale. If you don’t have either of these greens, think about stocking your freezer next summer. I will be posting blanching instructions in summer 2022.

This dish can be a side or a main with a green salad. As a main it serves 2-4, depending on the eaters. As a side it serves 4-6; cut each squash half into thirds for 6 guests.

Complete preparation time is about an hour, mostly for baking the squash.

Gather the ingredients below and get started. You will love the deep colors and flavors.

  • 1 acorn squash or other winter squash, cut lengthwise (stem down) and seeded

  • olive oil

  • salt and pepper

  • 1 red onion, diced

  • 3 cloves garlic, finely minced

  • 2 carrots, peeled and coarsely chopped

  • 1 pound Swiss chard, washed, and coarsely chopped (stems and all)

  • 2 tablespoons tomato paste

  • 1 tablespoon anchovy paste

  • 1/2 teaspoon red chili flakes

  • 1 cup full fat ricotta cheese

  • 1/2 cup grated parmesan

  • 1/4 cup Italian breadcrumbs

  • Chili oil for serving (Italian chili oil or Asian chili oil. I prefer my chili oil but there are many options)

Preheat oven to 400 F. Place squash on a baking dish, cut side up. Drizzle each half with 1/2 teaspoon olive oil, pinch of salt, and a few grinds of black pepper. Roast about an hour or until a fork easily pierces the squash.

In the meantime, heat 1 teaspoon olive oil in a large skillet over medium-high heat. When hot, but not smoking, add onions and garlic. Sauté, stirring until fragrant, 1-2 minutes. Reduce heat to medium-low, add carrots and sauté for 2 minutes, stirring frequently to prevent burning. Return heat to medium-high, add Swiss chard, 1 tablespoon olive oil, 1/2 teaspoon salt, and 1/2 teaspoon black pepper. Sauté for 4 minutes, stirring frequently. Remove from heat.

Add tomato paste, anchovy paste, and red pepper to Swiss chard and stir to combine. Fold in ricotta and parmesan cheese. Set aside.

Once squash is cooked, gently scrape a fork through the flesh to loosen. Add half the swiss chard mixture to each squash and top with half the breadcrumbs and a sprinkle of salt and pepper. Return the baking dish to the oven for 12-20 minutes, until bread crumbs are browned.

To serve, cut each half into two pieces and place on a plate. Drizzle the squash with chili oil and serve immediately.

Bon appetit people!

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Spaghetti Squash with Jammy Tomatoes

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Roasted Squash, Kale, Sage, & Hazelnut Panzanella Salad