Preheat the oven to 425 degrees and line a rimmed baking sheet with sprayed tin foil or parchment paper. Shake the chopped butternut squash in a plastic ziplock bag with 1 tablespoon of olive oil or avocado oil until it is evenly coated. Spread the squash out on the lined baking sheet and crack salt and pepper over the top.
Bake for 12-17 minutes or until you can easily pierce the squash pieces with a fork. (Timing will depend on how large you cut your pieces, so just keep checking every few minutes.)
While your squash is cooking, heat 1 tablespoon olive oil, the chopped shallots, 1 teaspoon salt, and the minced garlic over medium heat for about 3 to 4 minutes, stirring frequently, until the shallots start to soften and become fragrant.
Once your squash is done cooking, transfer it all to your blender along with the cooked shallots. Add maple syrup, melted butter, and vegetable broth. Careful not to fill your blender past the maximum fill line (you can work in batches if necessary, and stir in any remaining broth later).
Fasten the lid securely and blend on high, stopping once your soup is ultra creamy and warmed through, pour into bowls and enjoy!
Optional: Top with roasted pumpkin seeds, tyme, and heavy cream. (Use full fat coconut milk if GF.)