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Preheat oven to 400℉. Line a baking sheet with parchment paper.Place on baking sheet and rub acorn squash cavities with olive oil. Season with salt and pepper, and a sprinkle of nutmeg. Turn them flesh side down, and bake for 40 minutes or until tender.
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In the meantime, bring a pot of water to boil for the potatoes and season with salt. Boil the potatoes for about 30 minutes or until tender.
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At this point, brown your butter. Melt over medium heat. Once melted, begin to whisk constantly until butter gets foamy and starts to develop brown bits like pictured above. At this point, keep whisking until butter is very fragrant, nutty, and aromatic. Remove from heat because it can burn very quickly! This process can take a good 10 minutes.
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Once potatoes are tender, drain and add back to the pot.
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At this point, the acorn squash should be done. Let cool slightly and scoop out some of the flesh from each cavity, leaving enough flesh so that it remains a "bowl", and not just the skin. Add the acorn squash flesh to potatoes.
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Add the milk, half of the brown butter, maple syrup, a pinch of nutmeg, and half of the chives to the potato mixture. Mash with a potato masher or hand mixer. Season to taste with salt and pepper.
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Scoop potato mixture into acorn squash boats, and top with chopped bacon, remaining chives, and a drizzle of brown butter. Sprinkle top with an extra small pinch of nutmeg and salt and pepper if desired.