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A platter of golden brown pumpkin-shaped grilled cheese sandwiches with bell pepper stems and black olive spiders resting on parchment paper.
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Ultimate Grilled Cheese Halloween Sandwiches

Pumpkin-shaped grilled cheese sandwiches get a crisp, flavorful crust from garlic-herb mayo. Add an olive spider for a fun Halloween lunch or dinner!
Prep Time15 minutes
Cook Time24 minutes
Total Time39 minutes
Course: Main Dish
Cuisine: American
Keyword: grilled cheese, halloween
Servings: 8 people

Equipment

  • Circle cookie cutter
  • Small mixing bowl
  • Mixing spoon
  • Butter knife or spatula
  • Large Skillet
  • Spatula
  • Knife and cutting board for the olive spiders

Ingredients

  • 16 slices of bread such as Seattle sourdough sandwich rounds
  • 8 slices cheddar cheese
  • 4 Tablespoons mayonnaise
  • ½ teaspoon garlic powder
  • ½ teaspoon Italian seasoning
  • ¼ of an orange bell pepper sliced into slivers
  • 8 oz can whole black olives drained
US Customary - Metric

Instructions

  • Cut 8 slices of bread into circles using a cookie cutter, then set them aside.
  • Mix the mayonnaise, garlic powder, and Italian seasoning together in a small bowl.
  • Spread the mayonnaise mixture over one side of all 16 bread slices.
  • Spray a large skillet with nonstick cooking spray.
  • Place the 8 circle-cut pieces of bread in the skillet, mayonnaise-side down.
  • Cook the bread for 2 to 3 minutes, until browned, then remove the pieces from the skillet and set aside.
  • Place the remaining 8 slices of bread in the skillet, mayonnaise side down.
  • Place a slice of cheddar cheese on top of each piece of bread.
  • Place the browned bread pieces on top of the cheese, ensuring the browned side faces outward.
  • Insert a sliver of the orange bell pepper between the slices of bread to create a pumpkin stem.
  • Cook the sandwiches for 2 to 3 minutes until the bottom is browned and the cheese is melted.
  • Repeat until all the sandwiches are finished.
  • Create a spider out of black olives and place it on top of the warm sandwich so it slightly melts into the bread.
  • Serve the sandwiches warm alongside roasted tomato pepper soup.

Notes

  • Refrigerate: Place cooled leftover sandwiches in an airtight container for up to three days.
  • Reheat: Warm leftover sandwiches in a dry skillet over medium-low heat for 3 to 4 minutes per side to restore the crisp crust. Microwaving softens the bread and makes the texture rubbery.

Nutrition

Calories: 508kcal | Carbohydrates: 68g | Protein: 18g | Fat: 18g | Saturated Fat: 5g | Polyunsaturated Fat: 5g | Monounsaturated Fat: 6g | Trans Fat: 0.01g | Cholesterol: 20mg | Sodium: 1369mg | Potassium: 188mg | Fiber: 4g | Sugar: 6g | Vitamin A: 405IU | Vitamin C: 5mg | Calcium: 204mg | Iron: 5mg