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Put oven racks in upper and lower thirds of oven and preheat oven to 450F. Halve squash lengthwise, then cut off and discard stem ends.
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Scoop out seeds and cut squash lengthwise into 3/4-inch-wide wedges.
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Toss squash with black pepper, 3/4 teaspoon salt, and 2 tablespoons oil in a bowl,
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Then arrange, cut sides down, in 2 large shallow baking pans.
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Roast squash, switching position of pans halfway through roasting, until squash is tender and undersides of wedges are golden brown, 25 to 35 minutes.
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While squash roasts, mince garlic and mash to a paste with remaining 1/4 teaspoon salt.
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Transfer paste to a small bowl and whisk in lime juice, chile (to taste), cilantro, and remaining 1/4 cup oil until combined.
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Transfer squash, browned sides up, to a platter and drizzle with vinaigrette.