Twice-Roasted Squash with Parmesan Butter and Grains
['1 (3–4-lb.) kabocha, buttercup, or kuri squash', '3 oz. Parmesan, coarsely grated, plus more shaved for serving', '1/2 cup (1 stick) unsalted butter, room temperature', '1/2 tsp. finely grated lemon zest', 'Kosher salt, freshly ground pepper', '3 Tbsp. fresh lemon juice', '3 Tbsp. unseasoned rice vinegar', '3 Tbsp. extra-virgin olive oil', '1 Tbsp. honey', '2 scallions, thinly sliced', '11/2 cups cooked whole grains (such as barley, farro, and/or black or red quinoa)', '1/3 cup unsalted, roasted pumpkin seeds (pepitas)', '3 Tbsp. golden raisins', 'Shaved Parmesan (for serving)']
Place a rack in middle of oven; preheat to 300°F. Prick squash all over with the point of a sharp paring knife and arrange on a foil-lined rimmed baking sheet. Roast until very tender (knife should slide easily through the flesh), about 3 hours. Tear or cut squash in half and let sit until cool enough to handle.
Remove seeds from squash; discard. Scoop flesh into a medium bowl. Tear skin into 6 large (about 4x4") pieces and set aside on same baking sheet to be refilled later; discard any excess skin. Add grated Parmesan, butter, and lemon zest to bowl with flesh and mash together to combine; season with salt and pepper.
Carefully move rack to upper third of oven and increase oven temperature to 450°F. Divide mashed squash mixture among reserved pieces of skin and roast until top of flesh is beginning to brown, 10–12 minutes.
While the squash is roasting, whisk lemon juice, vinegar, oil, and honey in a large bowl. Add scallions, grains, pumpkin seeds, and raisins to dressing and toss to coat.
Arrange squash on a platter and spoon grain mixture and dressing over. Top with shaved Parmesan.
Whole squash can be roasted 4 days ahead. Keep intact and chill.
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