Preheat the oven to 400°F and coat a shallow baking pan with nonstick cooking spray.
Cut the squash in half crosswise, then trim a small slice from the rounded ends so you have a flat base for roasting. Use a spoon to scoop out the seeds and reserve them for another purpose or discard. Arrange the squash, seeded side up on the prepared baking pan.
Combine the melted butter and maple syrup in a small bowl and brush the mixture into the cavities and onto the cut surface of the squash. Season with salt and pepper.
Roast the squash until very tender, 50 to 55 minutes, basting with the melted butter mixture twice during cooking.
While the squash roasts, prepare the fruit compote. Melt the butter in a large skillet over medium heat. Add the onion and sauté until soft and translucent, 3 to 4 minutes. Add the cider, bourbon and brown sugar and bring the mixture to a simmer.
Add the apricots and cherries and cook over medium heat, stirring occasionally, until the mixture has thickened to the consistency of a light syrup, 8 to 12 minutes.
Add the pears and apple and continue cooking just until tender, 4 to 6 minutes longer.
When the squash are finished roasting, fill each with a portion of fruit compote, then return to the oven for an additional 5 minutes before serving.