Pork Chops and Squash with Pumpkin Seed Vinaigrette

2 Tbsp. shelled pumpkin seeds (pepitas)
3 lb. winter squash (acorn, kabocha, delicate, or butternut)
5 Tbsp. olive oil divided
kosher salt, freshly ground black pepper
4  1″ thick bone in pork chops
½ small garlic clove, finely grated
3 Tbsp. coarsely chopped fresh cilantro plus leaves for garnish
2 Tbsp. (or more) fresh lime juice

Preheat oven to 425 degrees. 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 and set aside.

Toss squash with 1 Tbsp oil on a large rimmed baking dish; 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 tbsp oil in 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 Tbsp chopped cilantro, 2 tbsp lime juice, reserved toasted pumpkin seeds, and remaining 3 tbsp oil in a small bowl to combine. Season vinaigrette with salt and pepper and more lime juice if desired.

Divide squash and pork among plates: spoon vinaigrette over. Top with cilantro leaves.