Cozy Acorn Squash Soup & Fancy Schmancy Cheddar, Brie & Apple Grilled Cheese

Like my title? I do.

There’s not much out there more comforting than a hot bowl of soup and some good grilled cheese.

Well, especially when you have just had your wisdom teeth out and can’t chew anything.

Especially, then. 


No, but really soup is one of my favorite things to cook and eat so I decided to take advantage of my lack of teeth and inability to consume anything more solid than baby food and experiment with a new soup! A FALL soup. Because that’s what I’m all about right now on the blog, fall, fall fall. I won’t shut up about it, really.

I see butternut squash soup all over the internet and being my difficult, non-conforming self, I decided to try something radically different than butternut squash……..

…ACORN squash.

I know, I’m a risk taker.


I always loved when my mom would roast acorn squash with a little cinnamon sugar in the oven. We would scoop it right out of the skin and eat it. Delish. Once I get those babies roasting in the oven, the house is consumed with that familiar smell and I am consumed with nostalgia.

To go with my soup creation I figured I would make some fancy grilled cheese. As an ode to the green apple in the soup, I put a thin slice of green apple, cheddar and, my favorite, a little smear of brie on the sourdough bread.

I was able to try the tiniest bite and force it down my gullet so I can attest to the combo working well, but because I was stubborn with my choice of bread and the apple, I couldn’t really eat it thanks to the wisdom teeth situation. That being said, my whole family liked it! Not one complaint from either kid about the sneaky apple on their grilled cheese or the “funny” tasting cheese. WIN!


The soup is really relatively easy once you do some chopping. The rest is mostly letting the oven and stove do it’s job while you sit on your couch and watch The Haunting of Hill House. <– That part is mandatory too for the soup to turn out right.

Ingredients for the Soup

  • 3 acorn squash
  • dash of salt & pepper
  • 1/8 tsp cinnamon
  • 1 large yellow onion
  • 3 carrots
  • 2 garlic cloves
  • 1 and 1/2 Granny Smith apple
  • 1/2 tsp dried ginger
  • 1/4 tsp rubbed sage
  • 1/4 tsp red pepper flakes
  • 1/2 tsp salt
  • 1/4 tsp all spice
  • 6 cups vegetable broth

Instructions for the Soup

  1. Preheat oven to 400 degrees F.
  2. Cut the acorn squash in half from the stem to bottom.
  3. Sprinkle with salt, pepper and cinnamon. Place facing down in roasting dish and bake for 45 minutes.
  4. While the squash bake, do your mis en place! Everything in it’s place. Dice the garlic and chop the onion, carrots and apple into uniform pieces for even cooking time.
  5. Remove squash from oven and allow to cool a bit before handling.
  6. In a large pot, heat about a tablespoon of olive oil. Once pot is hot, add the onion, carrots, garlic and apple. Saute about 7-10 minutes.
  7. Meanwhile, using a spoon remove the yellow flesh of the acorn squash. Spoon it into a bowl and leave behind the green skin of the squash.
  8. Add the ginger, sage, red pepper flakes, salt and all spice into the pot. Stir.
  9. Add the cooked acorn squash into the pot and combine.
  10. Add the vegetable broth and bring to a boil, stirring occasionally.
  11. Reduce heat and simmer for 25 minutes.
  12. Using a blender or immersion blender, puree the mixture to a smooth consistency.
  13. Garnish with fat free, plain Greek yogurt and serve.


Ingredients for the Grilled Cheese

  • loaf of sourdough bread
  • 1 Granny Smith Apple, thinly sliced
  • Aged White Cheddar Cheese (or your favorite), thinly sliced
  • Brie Cheese

Instructions for the Grilled Cheese

  1. Heat a griddle to medium high heat.
  2. Slice your sourdough bread and spread butter on one side of each slice.
  3. Layer your ingredients: slice of bread (butter side down), a smear of brie, apple slice, slice of cheddar, slice of bread (butter side up).
  4. Place on hot griddle and leave it alone 2-3 minutes until golden brown.
  5. Flip with a spatula and repeat until golden brown on the under side & cheese is nice and gooey.
  6. Enjoy!!


Drop a note with your fav fall soup down below so I can give it a go!

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