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Rub outside of each portabella mushroom cap with 1 tsp. olive oil. Place on a rimmed baking sheet.
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Heat 1 Tbsp. olive oil in a medium frying pan.
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Add onions, mushrooms, sage, and pepper and cook over medium-high heat until onions are tender.
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Add stuffing and butternut squash and cook to heat through.
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Fill each portabella mushroom cap with 1 oz. cream cheese and ¾ c. stuffing mixture.
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Top each with 1 Tbsp. chopped pecans and 2 Tbsp. shredded cheese.
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Bake at 350 degrees for 15-20 minutes.