Grab the 2 butternut squash and cut them in half, lengthwise. Grab a spoon and gut the seeds and flesh from the squash and place in a small bowl. You're going to use those seeds so don't discard them.
Next, peel the squash and dice into cubes. Make sure you keep the peelings. Do not discard.
Heat large pot or a dutch oven over medium-high heat. Add 1 Tablespoon of Extra Virgin Olive Oil and swirl around to coat. Add in the butternut squash peelings and seeds and saute for about 10 minutes or until lightly brown.
Add in 7 cups of water, whole allspice, Chinese Five Spice, whole black peppercorns, thyme sprigs, whole cloves, cinnamon stick, and fresh whole cranberries. Bring to a boil and then cover, reducing the heat and let simmer for 45 minutes.
After 45 minutes, you're going to strain the squash stock into a large bowl. You can now discard all the solid peelings, seeds and spices.
Return back to your large pot or dutch oven and add the remaining 3 Tablespoons of Extra-Virgin Olive Oil and shallot. Saute on medium heat for about 3- 5 minutes, or until the shallot starts to turn brown.
Add the cubed squash, cover and cook for 10 minutes, stirring occasionally.
Add the reserved squash broth and salt. Grab an orange and zest the peeling into the soup mixture. Bring to a boil, then cover and simmer for about 40 minutes or until the squash is tender.
Once done, place half of the squash mixture in a food processor. Blend until smooth.
Repeat the blending process with the remaining butternut squash. Once all the squash is blended, pour in the apple cider vinegar and stir with a large spoon until well combined.
Ladle soup into bowls. Top evenly with fresh chopped parsley, fresh chopped cranberries and pumpkin seeds.