This is pretty much the best grilled cheese I’ve ever made! Need I say more? So basically, I am just so excited that Thanksgiving is coming up and the grocery stores are filling up with fresh pumpkin again. I’m a huge fan of canned pumpkin for many recipes but sometimes fresh pumpkin really does the trick. That mildly sweet flavor and thick stringy flesh makes this a very filling grilled cheese and the sliced apple adds an extra layer of crunch. What a great way to begin the Fall season!

Pumpkin Grilled Cheese with Apples and Cheddar
makes two sandwiches

4 slices challah bread, sliced white or whole grain bread (Udi’s Gluten Free Bread is great for this also)
1 small pumpkin
1/2 gala apple, thinly sliced
1/4 cup sliced or shredded sharp cheddar
1/2 cup baby arugula
2 Tbsp butter

I bought a small pumpkin, often called a pie pumpkin, and washed the skin with soap and water. I preheated the oven to 350 degrees F.

I carefully sliced the pumpkin in half, from top to bottom, with a very sharp knife.

I scooped out the seeds and threw them away then placed the pumpkin halves in a large baking dish, face down. I filled the dish with 1/2 cup water then baked the pumpkin for 1 hour.

I removed the pumpkin from the oven, carefully flipped the halfs over and checked that the flesh was tender with a fork.

I set the cooked pumpkin aside to cool enough to handle, around 15 minutes. I scooped out the flesh and threw away the skin. You can store the flesh in an airtight container for up to 1 week in the fridge. Next up came the grilled cheese! I slathered butter on the outside of the sliced bread. I scooped some of the cooked pumpkin flesh on the bottom of one slice. I placed a layer of sliced apple on the pumpkin.

I added the sliced cheddar cheese then a handful of arugula.

I warmed a grill pan (you can also use a regular saucepan) over medium heat then added the stacked sandwich, butter side down, to the pan. I topped it with the second slice of buttered bread.

I pushed down on the sandwich with a spatula and listened to that beautiful sizzle. After three minutes on one side, I carefully flipped the sandwich, pressed down again with the spatula and cooked for another three minutes. The bread had beautiful brown grill marks but if you aren’t using a grill pan, the bread should be toasted on both sides. I removed the grilled cheese from the pan and sliced it in half.

I love the way the cheese melted right out of the sandwich and the apples stayed nice and crunchy!

Pumpkin Grilled Cheese with Apples and Cheddar
 
Author:
Serves: 2

Ingredients
  • 4 slices challah bread, sliced white or whole grain bread (Udi’s Gluten Free Bread is great for this also)
  • 1 small pumpkin
  • ½ gala apple, thinly sliced
  • ¼ cup sliced or shredded sharp cheddar
  • ½ cup baby arugula
  • 2 Tbsp butter

Instructions
Cooking the Pumpkin
  1. Preheat the oven to 350 degrees F.
  2. Wash the skin of the pumpkin with soap and water.
  3. Carefully slice the pumpkin in half, from top to bottom, with a very sharp knife.
  4. Scoop out the seeds and throw them away.
  5. Place the pumpkin halves in a large baking dish, face down.
  6. Fill the dish with ½ cup water then bake the pumpkin for 1 hour.
  7. Remove the pumpkin from the oven, carefully flip the halfs over and checked that the flesh is tender with a fork.
  8. Set the cooked pumpkin aside to cool enough to handle, around 15 minutes. Scoop out the flesh and throw away the skin. You can store the flesh in an airtight container for up to 1 week in the fridge.
Pumpkin Grilled Cheese
  1. Slather butter on the outside of the sliced bread.
  2. Scoop some of the cooked pumpkin flesh on the bottom of one slice.
  3. Place a layer of sliced apple on the pumpkin.
  4. Add the sliced cheddar cheese then a handful of arugula.
  5. Warmed a grill pan (you can also use a regular saucepan) over medium heat then add the stacked sandwich, butter side down, to the pan. Top it with the second slice of buttered bread.
  6. Push down on the sandwich with a spatula. After three minutes on one side, carefully flip the sandwich, press down again with the spatula and cook for another three minutes. The bread should be toasted on both sides.
  7. Remove the grilled cheese from the pan and slice it in half.
  8. Follow the same directions for the second sandwich.