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Sheet-Pan Roasted Squash and Feta Salad

['1 large or 2 small acorn or delicata squash (about 1 1/2 lb. total), halved lengthwise, seeded, cut into 1/4" slices', '1/4 tsp. freshly ground black pepper', '1/2 cup extra-virgin olive oil, divided', '1 1/2 tsp. kosher salt, divided', '4 slices country bread, cut into 1" cubes (about 4 cups)', '1/2 lb. Greek feta, cut into 1" cubes', '1/4 cup sherry or red wine vinegar', '1 tsp. honey', '1 tsp. thyme leaves', '1 head of radicchio or 1/2 head of escarole, leaves separated, torn into large pieces', 'Aleppo-style pepper (for serving; optional)']

Arrange a rack in top third of oven; preheat to 400°F. Toss squash, black pepper, 2 Tbsp. oil, and 1 tsp. salt on an 18x13" rimmed baking sheet and arrange in an even layer. Roast until squash is beginning to brown on one side, 10–15 minutes. Turn squash, then arrange bread and feta over. Roast until bread is lightly toasted and feta is soft and warmed through, 8–10 minutes.
Whisk vinegar, honey, thyme, and remaining 6 Tbsp. oil and 1/2 tsp. salt in a large bowl until well combined. Add radicchio and hot squash mixture and toss to combine.
Transfer to a platter and sprinkle with Aleppo pepper (if using).

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