Preparation time: 30 mins
Cooking time: 50 mins
Difficulty: Medium - experience needed
2 tablespoons shelled pumpkin seeds (pepitas)
3 pounds winter squash (such as acorn, kabocha, delicata, or butternut), halved, seeded, cut into 1-inch wedges
5 tablespoons olive oil, divided
Kosher salt, freshly ground pepper
4 1-inch-thick bone-in pork chops
1/2 small garlic clove, finely grated
3 tablespoons coarsely chopped fresh cilantro plus leaves for garnish
2 tablespoons (or more) fresh lime juice
Preheat oven to 425°. Spread out pumpkin seeds on a large rimmed baking sheet. Toast, tossing once, until just beginning to darken, about 4 minutes. Let cool. Coarsely chop; set aside.
Toss squash with 1 tablespoon oil on a large rimmed baking sheet; season with salt and pepper. Roast squash, turning occasionally, until golden brown and tender, 35-40 minutes.
When squash has been roasting for 30 minutes, heat 1 tablespoon oil in a large heavy skillet over medium-high heat. Season pork chops with salt and pepper and cook until brown, 5-8 minutes. Turn over and cook until pork is cooked through, about 3 minutes longer.
Whisk garlic, 3 tablespoons chopped cilantro, 2 tablespoons lime juice, reserved toasted pumpkin seeds, and remaining 3 tablespoons oil in a small bowl to combine. Season vinaigrette with salt, pepper, and more lime juice, if desired.
Divide squash and pork among plates; spoon vinaigrette over. Top with cilantro leaves.