Wash squash well and place on rimmed baking sheet. Bake for 1 - 2 hours (depending on size--see note below) until soft and starting to collapse.
When squash is nearly done, prepare topping if using. In a small saucepan, brown pecan pieces in butter, then remove from heat but keep warm. In a small frying pan heat oil until a drop of water sizzles. Place a few fresh sage leaves in hot oil and cook until they stop sizzling. Use a fork to remove to a plate. Repeat with the remaining sage leaves.
Remove squash from oven. Cut open with a large knife and expose inside of squash. Remove and discard seeds. Move squash to serving platter then drizzle with browned pecan butter and top with fried sage leaves and dried craanberries. Serve with brown sugar on the side.
Notes
For a simpler presentation, serve roasted squash with butter and brown sugar on the side.A larger or tougher squash may take longer to cook. Occasionally, I have gotten a squash that never got tender (even boiled for hours).
I am not a health professional and nutrition data is calculated programatically. Accuracy may vary with product selection, calculator accuracy, etc. Consult a professional for the best information.