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Step 1
Preheat oven to 425 degrees F. Line one or two baking sheets (depending on the size of your butternut squash) with parchment paper or foil, lightly greased with cooking spray.
Step 2
Spread the butternut squash chunks and halved Brussels sprouts evenly on the tray.
Step 3
Drizzle 2 tablespoons of olive oil over vegetables and sprinkle with salt and black pepper. Toss vegetables with your hands to distribute the oil evenly.
Step 4
Roast the vegetables for 25 minutes, tossing them gently 1 to 2 times during the roasting time to ensure that they caramelize evenly on all sides.
Step 5
Meanwhile, whisk together 1/2 tablespoon olive oil, balsamic vinegar, maple syrup, cinnamon, and cayenne pepper. Add the dried cranberries onto the baking sheet and toss the balsamic vinegar mixture evenly over vegetables. Toss the vegetables gently until they are lightly dressed. Roast for an additional 5-7 minutes until vegetables are tender and nicely browned. Serve warm, lukewarm, or cold.