Created by:

Melinda Strauss — Woodmere, NY

If autumn could talk, it would declare the Oktoberfest as its favorite sandwich. With Wisconsin aged cheddar, fresh pumpkin, apple and arugula on challah bread, this grilled cheese will make everyone wish fall were year-round.


Prepare pumpkin: Heat oven to 350°F. Wash pumpkin with soap and water; rinse and dry. Carefully slice pumpkin in half, from top to bottom, with very sharp knife. Scoop out seeds and discard. Place pumpkin halves in large baking dish, face down. Pour 1/2 cup water into dish; bake pumpkin 1 hour. Remove from oven; carefully flip halves over. Flesh should be cooked fork-tender. Set pumpkin aside until cool enough to handle, about 15 minutes. Scoop out flesh; discard skin. (Flesh may be stored in airtight container and refrigerated for up to 1 week if you are not using right away.)

Prepare sandwiches: Butter 1 side of each slice of bread. Spread a scoop of pumpkin over unbuttered sides of 2 bread slices. Layer apple slices, cheese and arugula on top of the pumpkin. Close sandwiches with remaining 2 slices of bread, buttered-side-up.

Heat grill or skillet over medium heat. Place sandwiches on pan. Push tops down with spatula to close tightly. Grill 3 minutes; carefully flip sandwich, press down again with spatula. Cook another 3 minutes. Bread should be toasted on both sides. Remove sandwiches from pan; slice in half and serve immediately.


  • 1 small pumpkin
  • 2 tablespoons butter
  • 4 slices challah, white or whole-grain bread
  • 1/2 Gala apple, thinly sliced
  • 1 cup (4 ounces) Wisconsin Sharp Cheddar cheese, shredded
  • 1/2 cup baby arugula
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