Step 1: Preheat your oven to 400°F (200°C). Line a large baking sheet with parchment paper for easy cleanup.
Step 2: Carefully cut each acorn squash in half lengthwise. Using a spoon, scoop out the seeds and fibrous strings from the center. You can save the seeds to roast later for a healthy snack!
Step 3: Place the acorn squash halves, cut-side up, on the prepared baking sheet. Drizzle each half with 1 tablespoon of olive oil, then season generously with salt and black pepper.
Step 4: Roast in the preheated oven for 20-25 minutes, or until the flesh is tender when pierced with a fork but still holds its shape. Roasting it face-up first allows for some caramelization.
Step 5: While the squash roasts, prepare the maple pecan glaze. In a small saucepan over medium-low heat, combine the maple syrup, melted butter, brown sugar, cinnamon, and a pinch of salt. Bring to a gentle simmer, stirring until the sugar dissolves. Remove from heat and stir in the chopped pecans.
Step 6: After the initial roasting time, carefully flip the acorn squash halves so they are cut-side down on the baking sheet. This allows the skin to crisp slightly. Return to the oven and roast for another 10 minutes.
Step 7: Flip the squash halves back to cut-side up. Spoon or brush the maple pecan glaze generously into the hollow of each squash and over the cut surfaces. Make sure those delicious pecans are evenly distributed.
Step 8: Return the glazed acorn squash to the oven and roast for an additional 10-15 minutes, or until the glaze is bubbling and slightly caramelized, and the squash is fork-tender throughout. Keep an eye on it to prevent the glaze from burning.
Step 9: Remove from the oven and let cool slightly before serving. The glaze will thicken as it cools. This roasted acorn squash recipe is best served warm.