Grilled Shrimp Skewers and Plantains

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1/4 cup plus 1 tablespoon extra-virgin olive oil, plus more for the grill

1/2 small shallot, finely chopped

1 tablespoon red wine vinegar

1/2 cup chopped fresh cilantro (leaves and tender stems)

1/2 teaspoon ground cumin

1/4 teaspoon dried oregano

Pinch of red pepper flakes

Kosher salt and freshly ground pepper

1 1/2 pounds peeled and deveined jumbo shrimp

2 Cubanelle chile peppers, seeded and cut into 1-inch pieces

3 ripe plantains, peeled and halved lengthwise