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1
Preheat oven to 425 degrees.
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2
Line a baking sheet with parchment.
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3
Place squash on baking sheet and toss with olive oil and salt to taste until lightly coated.
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4
Place apple on baking sheet and rub with oil.
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5
Place about a teaspoon of butter in the cavity where the core was.
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6
Place in oven and roast for 20 to 30 minutes, stirring squash every 10 minutes, until squash is tender and lightly colored and the apple is soft and falling apart.
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7
If the apple is done before the squash, remove it from the oven and set aside on a plate.
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8
Allow apple to cool until you can handle it, then peel and scrape any pulp clinging to the peel into a bowl.
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9
Core and combine baked apple with roasted squash.
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10
Meanwhile, place potatoes in a saucepan and cover by an inch with water.
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11
Bring to a boil, add salt to taste, reduce heat to medium-low and cover partially.
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12
Boil gently until tender, 25 to 30 minutes.
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13
Drain, return to pot and cover pot tightly.
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14
Let steam in the dry pot for 5 minutes.
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15
Heat milk and butter together until butter melts.
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16
Mash potatoes, squash and apple with a potato masher or in a standing mixer fitted with the paddle, or put through a food mill.
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17
Add milk and butter and mix until smooth.
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18
Season to taste with salt and pepper.
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19
Serve hot.
