Preheat your oven to 400°F and prepare a baking sheet lined with parchment paper.
Slice the acorn squash lengthwise and scoop out the seeds. Using a sharp knife, score the inside of each half with shallow crosshatch cuts.
Arrange the squash halves on the prepared baking pan. In a small bowl, combine the maple syrup, melted butter, and salt, stirring well. Brush this mixture evenly over the squash.
Roast the squash for 1 to 1½ hours, or until a fork easily pierces the flesh and it begins to crisp slightly. Once roasted, remove from the oven.
Adjust the oven rack so it sits about 6 inches below the broiler, then preheat the broiler.
In a large skillet over medium-high heat, brown the ground beef for about 8 to 10 minutes, breaking it apart as it cooks. Once browned, stir in the rosemary, oregano, and salt until combined.
Fill each squash half with approximately ½ cup of the beef mixture. If using Gouda, sprinkle it evenly over the filling. Drizzle a small amount of maple syrup on top.
Place the stuffed squash under the broiler and heat just until the cheese (if using) is melted and slightly golden.
Sprinkle additional salt to taste, if desired, and serve immediately.
Store any leftovers in an airtight container in the refrigerator for up to 4 days.