Preheat your oven to 425 F and line a baking tray with parchment paper. Place the squash on the pan and drizzle each half with just enough olive oil to lightly coat the the inside. Rub the oil over the inside of the squash and sprinkle it with salt and pepper. Bake, cut side down, until tender and completely cooked through, about 40 to 50 minutes. Set the squash aside until it’s cool enough to handle, about 10 minutes.
Line an additional baking tray with parchment paper and scatter the bread cubes in a single even layer. Drizzle the melted butter and salt over the bread and toss to coat. As soon as the squash comes out of the oven, turn the oven temperature down to 375 F and bake the croutons until golden brown, about 10-12 minutes, stirring half way through.
Meanwhile, in a large pot or dutch oven melt the butter over medium heat then add the sliced shallot and a generous pinch of salt. Cook over medium - low heat for 10 minutes, or until soft and translucent then add the garlic and cook until fragrant, stirring frequently about 2 minutes.
With a large spoon, scoop out the flesh of the roasted squash and transfer it into the pot, discard the skin. Next, add the chicken stock, maple syrup, thyme, cinnamon, nutmeg and another generous pinch of salt. Bring the soup to a low simmer, cover and let simmer for 10-15 minutes, then turn off the heat, pour in the cream and blend with an immersion blender (or in batches with a countertop blender, see notes below) until smooth. Taste and adjust the seasonings as needed.
To serve, divide the soup between bowls, top with croutons and a drizzle of olive oil. Serve right away.