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An ultra gooey grilled cheese sandwich with sweet raspberries, smoky chipotle and crispy bacon. Easy and incredibly delicious.
Prepare the bacon: Place rack in the center of the oven and preheat to 400 F. Line a large rimmed baking sheet with foil. Arrange bacon slices in a single layer on a flat ovenproof rack, then set the rack atop the prepared baking sheet. Put it into the oven. Bake bacon for 10-15 minutes, until crispy. Once cooked, carefully remove the pan from the oven, set bacon between two paper towels and pat dry. Cut each slice in half and set aside.
Preheat a cast-iron skillet to medium low. Melt half of the butter in the skillet. In a small bowl, gently smash and stir the raspberries, jam, and chipotle powder with the back of a spoon. The mixture should remain fairly chunky.
Assemble the sandwiches (makes 2 sandwiches): For each sandwich, layer one slice of bread with a quarter of the cheddar, a quarter of the berries, four half-slices of bacon (2 full slices), an additional quarter of the berries, then one additional quarter of the cheese.
Carefully set one loaded bread slice down in the buttered skillet. Place one remaining bread slice on top of the stack, then spread half of the remaining butter on the top of the bread.
Cook slowly until the bread is golden and the cheese is hot and melted, flipping once. This will take about 4 to 5 minutes per side. (I find it helps to place a lid or another heavy skillet directly over the pan.) Repeat cooking the second sandwich. Slice and serve immediately.
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