Begin by preheating your grill; for charcoal, set up for indirect cooking and aim for 350 to 400 degrees Fahrenheit. For gas, heat on high for 10 minutes, then lower to medium.
In a small bowl, combine chili powder, brown sugar, salt, cinnamon, and black pepper. Melt the butter in a saucepan over low heat, then mix it with the seasoning blend. Apply this mixture to the acorn squash rings by brushing or tossing to coat evenly.
Place the seasoned squash directly on the grill grates and cook for about 7 minutes until grill marks appear; flip and grill the other side for another 3-5 minutes. If they are not tender yet, transfer them to indirect heat and cover the lid until cooked through.
Once finished, brush the warm squash slices generously with maple syrup. Top with pumpkin seeds or pomegranate seeds before serving, and enjoy this delightful dish with loved ones!