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Pear and Fontina Grilled Cheese
with butternut squash soup

Active: 50 minTotal: 50 min

Adding fresh fruit to a grilled cheese sandwich makes it feel a bit fancy, but this one couldn't be easier. We like mild, quick-melting fontina cheese with the pears in this sandwich, but use another mild cheese if you prefer. Butternut squash soup on the side makes this a comforting meal that the whole family will love.


Roasted Butternut Squash (for 2 nights):
  • Butternut squash - 4 lbs, peeled and cubed
  • Oil, cooking - 2 Tbsp
Butternut Squash Soup:
  • Ginger - 1/2 tsp, grated
  • Shallots - 2 cloves, diced
  • Oil, cooking - 1 Tbsp
  • Sage, fresh - 4 leaves
  • Brown sugar - 1/2 tsp
  • Cumin - 1/8 tsp
  • Nutmeg, ground (opt) - 1/8 tsp
  • Roasted Butternut Squash (ingredients listed separately) - ~3 cups
  • Stock, any type - 2 1/2 cups
  • Yogurt, plain or Greek - 1/4 cup
Pear and Fontina Grilled Cheese:
  • Pears - 2, thinly sliced
  • Butter - 2 Tbsp + 2 Tbsp
  • Sandwich bread - 8 slices
  • Cheese, fontina - 4 slices (sub Swiss, provolone, or brie)

Nutrition Facts

Serving Size: 1 serving
Servings Per Recipe 4
Amount Per Serving
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% Daily Value
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  1. Butternut squash / Ginger / Shallots - Prep as directed. Store squash in one container. Combine ginger and shallots in another container. (Can be done up to 5 days ahead)
  2. Roast butternut squash - (This makes enough for 2 nights.) Heat oven to 425F / 218C degrees. Toss butternut squash with oil (portion for squash) and some salt and pepper. Spread butternut squash out onto a sheet pan. Roast for 20 to 30 minutes, shaking the pan halfway through cooking, until golden and caramelized. (Can be done up to 5 days ahead)
  3. Pears - Thinly slice pears.


  1. Heat a saucepan with oil (portion for soup) over medium heat. Add ginger, shallots, and sage. Saute until shallots are very tender and sage is very dark and tender, 5 to 6 minutes. (Note: It is important to cook the sage until very tender to remove bitterness that is present in the raw herb.)
  2. Add brown sugar, cumin, and nutmeg. Saute for 1 minute.
  3. Add half of the roasted butternut squash (reserve remaining half) and stock. Bring soup to a simmer and simmer for 5 minutes to let the squash get very soft and the flavors come together.
  4. While soup is simmering, heat a griddle or large skillet over medium heat. Melt first portion of butter in the pan and add half the bread. Top with cheese, pear slices (in a single layer), and remaining bread slices. Cook on one side until golden brown.
  5. Add second portion of butter to pan and flip sandwiches with a spatula, moving them around to coat them in the butter. Continue cooking until golden brown on the second side.
  6. While sandwiches are cooking, blend soup until smooth using an immersion blender or standing blender. Taste soup and season with some salt and pepper. If it is very thick, you can thin it out a bit with some water.
  7. Serve soup with a spoonful of yogurt on top and sandwiches on the side. Enjoy!

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This meal has 32 reviews

Made a different version of the soup, but the grilled cheese was excellent!

By: Marin
Posted: Dec 09, 2019
Diet: Original

I went with the maple balsamic pork chop salad and butternut squash soup because of a dairy allergy (wish I could have that grilled cheese sandwich!). The porkchops were delicious with the pears and vinaigrette, but I had to add more stock to the soup to thin it out. All around very tasty and different from what we usually eat.

By: Natascha
Posted: Dec 04, 2019
Diet: Paleo

Love this soup recipe!

By: Jessica
Posted: Nov 27, 2019
Diet: Original

Yummy! I ended up using gouda and was still really good! Though my kids had us take off the pears. I wish I would have used more butternut squash to thicken it up but I will this second time around! And I didn't use any brown sugar and was still sweet. Thanks CS for another yummy one!

By: Carlene
Posted: Nov 24, 2019
Diet: Vegetarian

I always really enjoy Cooksmarts grilled cheese variations, and this was no exception! This meal came together much more quickly than I expected, and had so many great fall flavors.

By: Melissa
Posted: Nov 24, 2019
Diet: Original

Loved it. Used Brie. Was a really nice, comforting meal for a snowy evening.

By: Tiffany
Posted: Nov 21, 2019
Diet: Original