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Caramelized Pumpkin Grilled Cheese

Pumpkin Grilled Cheese

Savor all the flavors of fall in one comforting bite. Don’t want dairy? Omit the cheese and enjoy this healthy, earthy- tangy topper with latkes, crostini, or pasta. Use any remaining pumpkin mixture as an addition to Greek yogurt, pasta dishes, eggs, or soups. 

  • Duration
  • Cook Time
  • Prep Time
  • 4Servings


Onion Jam

  • ¼ cup extra virgin olive oil
  • 1 onion, halved and thinly sliced
  • ¼ cup apple cider vinegar
  • ¼ cup maple syrup

Grilled Cheese

  • 3-pound pie pumpkin, or butternut squash, peeled, seeded, and cut into ½-inch cubes
  • ¼ cup extra virgin olive oil, plus more for drizzling
  • ½ teaspoon crushed red pepper 
  • Kosher salt
  • 8 thick slices country or whole wheat bread, or leftover challah
  • Several garlic cloves, peeled but not cut
  • 1 heaping cup ricotta
  • Flake salt
  • ¼ cup chopped mint



1. In a small saucepan, heat ¼ cup of evoo over medium heat. Add onions, stir, and cook for 15 minutes, until they begin to soften and darken.

2. Add vinegar and syrup; reduce for 15 to 30 minutes until it looks like jam and tastes tart-sweet. Place in a container to cool.


1. In a heavy pot or Dutch oven, add pumpkin/squash, ¼ cup of olive oil, crushed red pepper, and pinch of salt. With the lid on, cook over medium-high heat, stirring occasionally for 15 to 20 minutes, until pumpkin is tender. Adjust the heat if necessary so pumpkin doesn’t burn.

2. Add onion mixture to cooked pumpkin, stirring gently to preserve chunky pumpkin texture. Taste, and season with salt or more red pepper, if needed.

3. Drizzle bread slices with olive oil and toast on a griddle, pan, or under the broiler. Rub with garlic clove once toasted.

4. Spread a thick layer of ricotta on bread, then an equal amount of the pumpkin-onion mixture. Sprinkle with flake salt salt and a drizzle of evoo. Top with chopped mint. Serve immediately.

5. Store leftover pumpkin mixture, covered, in the refrigerator for up to 3 days, or freeze for 2 months.

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