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Step 1
Preheat the oven to 400°F (200°C). Line a large baking sheet with parchment paper and set aside.
Step 2
Combine 3 Tablespoons olive oil, maple syrup, vinegar, cinnamon, nutmeg, salt and pepper in a bowl. Set aside.
Step 3
Using a sharp knife cut off the very top and bottom of each squash to create a flat base on each side (being careful not to cut through the center cavity). Slice the squash in half, scraping out the seeds to create individual bowls for the stuffing. Generously brush each squash half with about half of the olive oil mixture. Place cut side up on the prepared baking sheet, make a few slits in the flesh using a pairing knife (this will ensure an even roasting), and roast for 40-50 minutes, or until fork tender.
Step 4
Place the rinsed rice in a pot with 3 times its volume of water. Bring to a boil, then lower the heat, cover, and continue to cook until all water is absorbed, adding the dried cranberries a couple of minutes before you turn off the heat. Remove from heat, add the remaining half of the olive oil mixture, cover again and let sit covered, so the steam will plump the rice and fruits. Taste and adjust the seasoning as needed.
Step 5
In a large skillet, heat one Tablespoon butter on medium heat. Once hot, add the shallots and cook until soft and translucent, about a minute or two. Add the wild mushrooms and sauté for one more minute, until soft. Sprinkle with thyme, stir, and cook for another minute. Add the mushroom mixture to the cooked rice and stir well.
Step 6
Once Squash has finished roasting, remove from the oven and fill each half with prepared stuffing mixture.
Step 7
Bake for about 5-10 minutes, then remove and sprinkle the Parmesan cheese on top. Bake 5 additional minutes, until the cheese is melted. Serve warm.