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Preheat oven to 350 degrees. Cut squash into wedges and arrange on baking sheet. Season with sea salt and pepper and drizzle with oil. Bake 45 minutes.
Meanwhile, in small bowl, whisk together 2 tablespoons olive oil and minced garlic. Season with sea salt and pepper.
Generously brush each Portobello on both sides with oil marinade. Allow to rest 10 minutes.
When squash is ready, remove skin and transfer to large bowl. Using a potato masher, lightly mash until desired consistency and adjust with sea salt and pepper.
Heat skillet over medium heat and cook mushrooms 5-10 minutes on each side, until tender.
Spoon mashed squash onto each portobello mushroom. Top with roasted walnuts, if desired.