Preheat oven to 375°.
Toss cubed squash with 3 tablespoons olive oil, 2 teaspoons kosher salt & 1 teaspoon black pepper. Place on a large rimmed baking sheet, making sure all the squash fits in one layer. Top with 6-8 sprigs of fresh thyme (or 2 teaspoons dried). Roast for 60 minutes, or until squash has slightly browned & is tender all the way through. Once cooked, remove thyme stems & set aside.
In a large heavy bottom pot or Dutch Oven, sauté Linguica until crispy & heated through. Remove Linguica from the pan & heat remaining 3 tablespoons olive oil over medium heat (if the Linguica renders a lot of fat, you can use less olive oil). Sauté carrots, celery & onion with ½ teaspoon salt & ¼ teaspoon pepper until soft but not browned, 7-10 minutes, stirring occasionally.
Once veggies are cooked, turn the heat to high & add wine. Let the wine bubble up & using a wooden spoon, scrape up any browned bits from the bottom of the pan. Cook until wine has reduced by half.
Add cooked squash & broth to the pot. Stir to combine.
Bring the soup to a boil, then reduce the heat to a low simmer. Simmer for 5 minutes.
To blend the soup in a blender: pour half of the soup into a high powered blender & blend until smooth. Repeat with remaining half then return soup to the pot.
To blend the soup with a hand blender: place hand blender directly into the pot & carefully blend until smooth.
Taste the soup & if needed, add 1 teaspoon salt. If the soup needs more broth, add extra both 1 tablespoon at a time until you reached your desired consistency.
Finish the soup with 2 tablespoons heavy cream & serve topped with Linguica.
