Line a baking sheet with parchment paper and preheat oven to 375 degrees.
Brush flesh side of squashes with olive oil, salt and pepper. Bake for 50 minutes. Meanwhile, sauté garlic in butter on low for three minutes.
Scoop out the flesh into a large bowl (or blender) and add sautéed garlic and Smoky Sweet Jerk Seasoning. Puree with an immersion blender, food processor or blender adding 1-2 tbsp of heavy cream or chicken broth at a time to reach desired consistency. Add more salt to taste.
*Recommendation: Serve with roasted squash seeds and crème fraiche. This would be perfect side dish for the holidays, or serving it with a rotisserie chicken would be an easy weeknight meal.
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