Preheat your oven to 400 degrees F. Set a folded kitchen towel on your cutting board to hold the squash steady. Cut each acorn squash in half from stem to tip using a firm, careful motion. A sharp chef's knife makes this much easier. If the squash feels unstable, slice a thin strip off the round bottom first so it sits flat.

Use a large spoon or ice cream scoop to scrape out the seeds and stringy fibers from each half. Discard the seeds or save them to roast separately with salt later. Place the four squash halves cut-side up in a baking dish or rimmed baking sheet.

In a small bowl, stir together the melted butter, 2 tablespoons of the maple syrup, cinnamon, salt, and pepper. Brush this mixture generously over the cut surface and into the hollow cavity of each squash half. Pour the 1/4 cup of water into the bottom of the baking dish around the squash. This creates a bit of steam that helps the squash cook through without drying out.

Place the baking dish in the oven and roast for 30 minutes. The squash should be starting to soften at this point but will not be fully done yet. Pull the dish out carefully.

Brush the remaining 1 tablespoon of maple syrup evenly over each squash half. Return the dish to the oven and roast for another 12 to 15 minutes. The squash is done when a fork slides into the thickest part of the flesh with no resistance and the edges are caramelized and a deep golden color. The cavity may pool slightly with buttery syrup and that is exactly what you want.

Remove the baking dish from the oven and let the squash rest for 5 minutes before serving. Place each half on a plate or serve right from the baking dish. Spoon any pooled syrup from the cavity back over the top just before serving.