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Preheat oven to 450°F. Coat a large baking sheet with nonstick spray; set aside.
In a large mixing bowl, combine squash, mushrooms, bell pepper and 3 tablespoons olive oil, stirring to coat well. Season with 1/8 teaspoon each salt and pepper. Arrange vegetables on the prepared baking sheet. Roast vegetables for 20 to 25 minutes or until brown and tender, stirring halfway through. Remove from oven and stir in cilantro.
Place a tortilla on work surface; sprinkle 1/2 cup the shredded cheese over the one half of tortilla. Top with about 1/3 cup of the roasted vegetables. Fold tortilla in half over the filling. Repeat with the remaining tortillas, shredded cheese and roasted vegetables. Arrange quesadillas in a single layer on a second baking sheet, baking in batches if necessary. Bake for 2 to 3 minutes. Flip quesadillas over and bake for 2 to 3 minutes more or until cheese is melted and tortillas are slightly browned. Let cool 1 minute; cut into wedges.
Meanwhile, in a large bowl, combine cucumber, cantaloupe, arugula, lime juice, and the remaining 1 tablespoon oil. Toss to coat. Season with the remaining 1/8 teaspoon each salt and pepper; sprinkle with queso fresco. Serve quesadillas with melon-cucumber salad, salsa, guacamole and sour cream.