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Easy Caramelized Roasted Acorn Squash Rings Recipe

roasted acorn squash rings - featured image

These caramelized roasted acorn squash rings are a showstopping side dish with a double-sided caramelization trick that creates a perfect balance of sweet and savory. Easy to prep ahead and always a crowd-pleaser.

Ingredients

Scale
  • 2 medium acorn squash (about 1.5 pounds each)
  • 3 tablespoons unsalted butter, melted
  • 3 tablespoons brown sugar, packed
  • 1 teaspoon ground cinnamon
  • 1/2 teaspoon ground nutmeg
  • 1/2 teaspoon salt
  • 1/4 teaspoon black pepper
  • 2 tablespoons maple syrup (optional, for glaze)
  • 1 tablespoon balsamic vinegar (optional, for glaze)
  • Fresh thyme or rosemary sprigs (for garnish, optional)
  • Flaky sea salt (for garnish, optional)

Instructions

  1. Preheat your oven to 400°F (200°C). Position the rack in the middle of the oven. Line a large baking sheet with parchment paper or a silicone baking mat.
  2. Prepare the squash: Using a sharp chef’s knife, cut off the stem end and bottom tip of each acorn squash so they sit flat. Cut each squash crosswise into 1/2-inch (1.25 cm) thick rings. Use a spoon or small knife to scrape out the seeds and stringy pulp from the center of each ring.
  3. Make the butter mixture: In a small bowl, combine the melted butter, brown sugar, cinnamon, nutmeg, salt, and black pepper. Stir until well combined and the sugar has mostly dissolved.
  4. Arrange the rings in a single layer on the prepared baking sheet, making sure they are not touching each other.
  5. Brush the first side: Using a pastry brush, generously brush the butter mixture onto the top of each ring. Reserve about half of the mixture for the second side.
  6. Roast for 15 minutes.
  7. Flip and brush again: After 15 minutes, carefully remove the baking sheet from the oven. Using a spatula, flip each ring over. Brush the second side with the remaining butter mixture.
  8. Roast for another 12-15 minutes, until the rings are tender and deeply caramelized on both sides. For extra caramelization, switch the oven to broil for the last 1-2 minutes, watching carefully.
  9. Optional glaze step: If using the maple-balsamic glaze, whisk together the maple syrup and balsamic vinegar in a small bowl. During the last 5 minutes of roasting, brush this mixture over the rings.
  10. Rest and garnish: Remove the baking sheet from the oven and let the rings rest for 2-3 minutes. Transfer to a serving platter, arrange in an overlapping pattern, and sprinkle with flaky sea salt and fresh herb sprigs if desired. Serve warm or at room temperature.

Notes

For even caramelization, cut rings as close to 1/2-inch thick as possible. Don’t skip flipping the rings halfway through. If your oven runs hot, reduce temperature to 375°F and extend cooking time by 5-7 minutes. Leftovers can be stored in an airtight container in the refrigerator for up to 4 days. Reheat in the oven at 350°F for 5-7 minutes or in an air fryer at 350°F for 3-4 minutes. Avoid the microwave.

Nutrition

Keywords: acorn squash, roasted squash, caramelized squash, fall side dish, holiday side dish, gluten-free, vegetarian