3 lbs hard squash such as kabocha, acorn, or butternut squash
1 tablespoon olive oil
1 teaspoon fresh thyme leaves
1 cup fresh or frozen cranberries
1/4 cup maple syrup
1/2 cup freshly squeezed orange juice
1/2 teaspoon orange zest
1 cinnamon stick
2 tablespoons unsalted butter
Coarse kosher salt, to taste
Freshly cracked black pepper, to taste
Preheat oven to 300˚F. Spread pecans on a baking sheet and toast until golden and fragrant, about 10-15 minutes. Remove and let cool. If using pecan halves, roughly chop.
Increase oven temperature to 375˚F.
Trim and prepare squash. If using butternut squash, peel, seed, and cut into wedges. If using acorn or kabocha squash, you can leave the skin on; simply remove seeds and cut into wedges. Toss prepared squash with olive oil and thyme and season with salt and pepper. Spread on a foil-lined baking sheet and roast in the preheated oven until golden brown and tender, about 45-60 minutes.
Meanwhile, combine cranberries, maple syrup, orange juice, orange zest, and cinnamon stick in a small pot over medium heat. Bring to a simmer, then reduce heat to low and simmer until cranberries have just burst and liquid starts to thicken, about 10 minutes. Remove from heat and stir in toasted chopped pecans, butter, and ¼ teaspoon salt.
Remove squash from the oven and pile onto a serving platter or bowl. Spoon warm cranberry-pecan sauce generously over the top. Serve immediately with additional cranberry-pecan sauce on the side.