Heat oven to 400°F. Set up the fondue pot stand in the Jack-O-Lantern.
Cut end off garlic bulb, exposing the tops of the cloves. Place on a piece of foil then drizzle with EVOO, salt and pepper. Wrap garlic up in the foil and roast 45-50 minutes. Let cool then squish out the garlic cloves from the skins into a food processor.
While garlic is roasting, peel and chop squash into 1/2-inch cubes. Place on a large baking sheet and dress with EVOO to coat lightly. Season with salt, pepper and a drizzle of maple syrup. Roast to golden at edges and very tender, about 35 minutes.
Once the squash is done, place into food processor along with the roasted garlic and purée until smooth. You should have about 2 cups worth or a bit more.