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1
Roast your apple chunks: Preheat oven to 400 degrees. Spread apple chunks on a baking sheet, toss with 1 T. brown sugar, sprinkle with 2 T. apple cider, dot with 1 T. butter, and sprinkle with a generous pinch of salt. Roast for about 30 minutes (check after 20). They are done when deep golden on one side, and they easily collapse when prodded. Immediately pour an additional 1/4 cup (4 T.) apple cider over the apples to deglaze the pan a bit.
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2
While your apples are roasting, caramelize your onions and carrots: In a large pot, heat 1 T. butter with 1 T. olive oil over medium heat. Add the onions, carrots, and thyme and cook until the onions are deep golden and beginning to brown and carrots are softened. You want some good brown bits on the bottom of the pan as well.
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3
Add the roasted apples to the pan and toss with the onion & carrot mixture. Cook, stirring until all of the apple cider has bubbled away. (If your apples are not done by the time your onions are, wait for them to finish before moving on. Just take the onion & carrot mixture off the heat and wait for those apples).
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4
Deglaze the pan with 2 T. of sherry, stirring and scraping the brown bits on the pan.
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5
When all the liquid is gone, add 1 c. apple cider and 1 1/2 c. water or vegetable stock. Stir to combine. Bring to a boil and then let simmer briefly (5 minutes or so) to combine the flavors.
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6
Shred your sharp cheddar into the soup, stirring to melt the shreds
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7
Transfer to a blender and (carefully!- keep the little hole in the lid of the blender open and cover with a dish towel when blending) blend until smooth. Transfer back to the pan to warm through.
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8
Stir in 2 T. of butter to enrich the soup. Add your spices and season with salt and pepper. Taste, adding more spices as you see fit.