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These pumpkin-shaped Grilled Cheese Sandwiches use a garlic-and-herb mayo to give the bread a crisp, flavorful crust. Top them with an olive spider for a spooky, fun Halloween lunch or dinner.
These Halloween Sandwiches are perfect for dipping in a bowl of Tomato Tortellini Soup, keeping you cozy all season long.
Recipe Tips
A few do’s and don’ts to help you make the best Halloween sandwiches ever.
- Be sure to spread the seasoned mayo to the edges. This ensures the entire piece of bread gets golden brown, slightly crispy, and super flavorful.
- Do not be tempted to turn the heat up. Otherwise, the bread can burn quickly. Keep the heat medium-low so the cheese melts without burning the bread.
- Make the olive spiders first. Have the spiders ready before cooking the sandwiches so you can add them while the cheese is still warm without overcooking the sandwiches.
Ingredients
- Bread: You need 16 slices of bread, such as Seattle sourdough sandwich rounds. Bread with a little structure helps, since the shaped pieces need to hold together during cooking. You can use white sandwich bread, wheat bread, potato bread, or another sourdough instead. Choose slices that are large enough for your cookie cutter.
- Cheddar cheese: Eight slices create the gooey center and add the orange color that makes these sandwiches look more like pumpkins. Medium or sharp cheddar both work. American cheese, Colby Jack, or Monterey Jack can replace cheddar when you prefer a softer melt.
- Mayonnaise: Four tablespoons coat the bread and create that crisp golden exterior. Spread it in a thin, even layer rather than piling it on. Softened butter can replace the mayonnaise, though the flavor and browning will differ slightly.
- Garlic powder: Half a teaspoon seasons the mayonnaise without adding pieces of garlic that can scorch in the skillet. Onion powder makes an easy swap, or use a smaller amount of both seasonings for a different flavor.
- Italian seasoning: Half a teaspoon adds dried herb flavor throughout the mayonnaise mixture. A blend with oregano, basil, or thyme works nicely. Dried parsley or oregano can replace it.
- Orange bell pepper: Cut one quarter of an orange bell pepper into narrow slivers for the pumpkin stems. Green bell pepper works too and gives the stem more contrast against the sandwich.
- Whole black olives: One 8-ounce can provides the pieces for the spiders. Drain the olives well, then pat them dry before cutting. Sliced black olives can work when that is what you have, though whole olives are easier to shape into bodies and legs.
How to Make Halloween Grilled Cheese Sandwiches
Shape the bread first, then coat it with garlic herb mayonnaise and toast in batches. Cheddar melts between the bread pieces, orange pepper forms each pumpkin stem, and a small black olive spider finishes the sandwich.
- Shape the Bread: Cut 8 slices of bread into circles using a 3-inch cookie cutter. Set these rounds aside. Keep the remaining 8 slices whole for the sandwich bases.
- Mix the Spread: In a small bowl, stir the 4 tablespoons of mayonnaise, ½ teaspoon of garlic powder, and ½ teaspoon of Italian seasoning together until smooth.
- Coat the Bread: Spread the seasoned mayonnaise mixture over one side of all 16 slices of bread.
- Brown the Top Rounds: Coat a large skillet with nonstick cooking spray and place it over medium heat. Arrange the 8 round bread pieces in the skillet, mayonnaise side down. Cook for 2 to 3 minutes until golden brown, then transfer the pieces to a plate.
- Build the Sandwiches: Place the remaining 8 slices of bread in the skillet, mayonnaise side down. Top each slice with one slice of cheddar cheese. Place the toasted bread rounds on top of the cheese with the browned side facing upward.
- Add the Stems and Cook: Slip one thin sliver of orange bell pepper between the two slices of bread at the top edge of each sandwich. Cook the sandwiches for 2 to 3 minutes until the bottom slices turn golden brown and the cheese melts. Repeat in batches if needed.
- Serve: Transfer the finished sandwiches to plates and serve warm alongside roasted tomato pepper soup.
Recipe FAQs
What if I don’t have a pumpkin cookie cutter?
Just improvise with a round cookie cutter or the rim of a wide glass for a similar look.
How do I make the olive spiders?
Use two olives. Slice one in half lengthwise for each body, then cut the other one into thin strips for the legs.
Can I make these ahead of time?
These are best served warm and fresh. Slice the olives ahead of time and cut the bread, but wait to cook the sandwiches until just before serving.
Ideas for Leftover Bread Scraps
- Cookie cutters leave plenty of bread around the edges, and those pieces do not need to go to waste.
- Toast them with a little olive oil and seasoning for croutons. Freeze the scraps and turn them into breadcrumbs later, or use them for a small batch of bread pudding.
Did you make these Halloween grilled cheese sandwiches? Leave a rating and review in the recipe card below.
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!
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
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
Nutrition information is automatically calculated, so should only be used as an approximation.
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