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Preheat the oven to 425°F. Line a sheet pan with parchment or foil.
Prep the delicata squash by cutting it in half lengthwise, scooping out the seeds, and slicing into half-moons about ½ inch thick. Trim the root end of the Brussels sprouts and cut them in half.
Arrange the Brussels sprouts and squash on the prepared pan in a single layer, toss with ¼ cup of olive oil, season with salt and freshly ground pepper, and transfer to the oven to roast until tender-crisp and golden, 15 to 20 minutes. In the last five minutes, add the scallions brushed with 1 tbsp olive oil.
Brush 2 pieces of pita with olive oil, season with salt, and toast in the oven until crisp, about 5 minutes. Once cool, break the pita bread into bite-sized pieces.
Process the cooled scallions in a blender or food processor until smooth, combine with 4 tbsp olive oil, red wine vinegar, and Dijon mustard. Blend or whisk until fully combined, season with salt and pepper to taste.
Pick the mint and parsley leaves and toss the stems. In a large bowl, combine the roasted veggies, herbs, feta, and toasted pita. Drizzle with ⅓ cup of the roasted scallion vinaigrette and turn to coat. Sprinkle with sumac, grind with pepper, and serve.