Ingredients:

  • 2 medium Acorn Squash
  • 4 Tbsp Unsalted Butter, softened (divided)
  • 1/4 cup Dark Brown Sugar, packed
  • 2 Tbsp Maple Syrup (Grade A Dark)
  • 1/4 tsp Kosher Salt (divided)
  • 1/2 tsp Ground Cinnamon
  • 1/4 cup Hot Water or Broth

Instructions:

  1. Preheat the oven to 400°F (200°C).
  2. Prep the Squash: Wash the acorn squash thoroughly. Carefully slice each squash in half lengthwise from stem to tip.
  3. Scoop & Score: Use a spoon to scrape out all the seeds and stringy membranes from the cavity. Lightly score the flesh of the squash halves with the tip of a knife (about 1/4 inch deep).
  4. Initial Seasoning: Place 1 Tbsp of the softened butter into a small bowl. Rub the cut surfaces of the squash halves generously with this butter. Sprinkle lightly with a pinch of salt.
  5. Set up the Pan: Pour the 1/4 cup of hot water or broth into the baking dish. Arrange the squash halves cut-side down in the dish.
  6. First Bake: Roast for 25–30 minutes, or until the squash has begun to soften significantly.
  7. Prepare the Glaze: While the squash is baking, combine the remaining 3 Tbsp of butter, brown sugar, maple syrup, cinnamon, and the remaining salt in a small bowl. Mix thoroughly until a thick paste forms.
  8. Flip and Fill: Remove the squash from the oven. Carefully flip all the halves so they are now cut-side up (cavities facing upwards).
  9. Glaze Application: Divide the glaze mixture evenly among the four squash cavities. Spoon the mixture directly into the center of each half.
  10. Final Roast: Return the squash to the oven for another 15–20 minutes. The squash is done when the flesh is fork-tender and the sugar mixture is bubbling, caramelized, and dark golden brown.
  11. Rest and Serve: Remove the pan from the oven. Allow the squash to rest in the pan for 5 minutes before serving. The glaze will thicken slightly as it cools.