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Step 1
Heat oven to 425°F and place oven rack in top third. Brush rimmed baking sheet with oil.
Step 2
Melt 2 tablespoons butter in small skillet on medium and cook gently, swirling pan until butter starts to turn golden brown. Add chopped sage and, as soon as butter is evenly browned, transfer to medium bowl and let cool slightly. Once cooled, mash remaining 2 tablespoons butter into browned butter to make paste, then add garlic, maple syrup and a pinch each of salt and pepper.
Step 3
Meanwhile, peel butternut squash and halve lengthwise, then scoop out and discard seeds. Hasselback the squash (see tip below): With sharp knife, make vertical cuts in rounded side of each squash half, 1/8 inch to 1/4 inch apart, being sure to stop at least 1/4 inch from bottom (do not cut all the way through). Place a few small sage leaves and chile slices in slits.
Step 4
Season squash with 1/2 teaspoon each salt and pepper and brush with some butter mixture. Roast, brushing with butter mixture every 10 min., until tender, 65 to 75 minutes. Serve drizzled with additional syrup if desired.