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Roasted Shallot and Tomato Quesadillas

Why settle for a bum wrap when you can get a great quesadilla?

6 standard quesadillas or 12 rolled quesadillas


About 2 hours


Melted cheese in crisp, flaky tortillas finds bright flavor punctuation in the form of sweet roasted shallots and tomatoes and homemade pickled jalapeños.

Cooking Remarks

New to the experience of homemade pickled jalapeños? Crunchy, searing, ever-so-slightly sweet with soaring green chile notes, these are quick to make and will last forever. Well, forever in theory. In truth, they vanish pretty fast. At the very least, try to keep some on hand for mixing into scrambled eggs or serving with cheese and crackers.

If your tortillas aren’t perfectly round and uniform, make rolled quesadillas instead of standard flat ones. We’ll show you how below.

equipment mise en place

For this recipe, you will need a box grater; a fine rasp-style grater; a sharp paring knife; a chef’s knife; three smallish and two medium-sized mixing bowls; a rimmed baking sheet or small baking dish; an old-fashioned vegetable peeler (one with a narrow swiveling blade and pointed tip); a medium nonreactive saucepan with a lid; a footed colander; a heavy 10-inch square or round griddle, preferably well-seasoned cast-iron; and a metal spatula. To protect your hands from the chiles’ heat, you may also want to have on hand a pair of thin, snug-fitting rubber gloves, such as surgical gloves.

  • for the roasted shallots and tomatoes:

    • 6 to 8
      large shallots
    • 2
      teaspoons olive oil
    • Fine sea salt and freshly ground black pepper 

    • 1
      pint ripe grape tomatoes
  • for the pickled jalapeños:

    • 2
      cups spring or filtered water
    • Fine sea salt 

    • 12
      medium-large jalapeño chiles (about 6 ounces total weight)

    • ½
      cup distilled white vinegar

    • 1
      tablespoon honey

    • 1
      large garlic clove, peeled

  • for the lime-cilantro cream:

    • 8
      ounces (1 cup) Mexican crema or sour cream
    • ½
      teaspoon finely grated lime zest

    • 2
      teaspoons juice from ½ a juicy lime

    • 2
      tablespoons minced fresh cilantro

    • ½
      teaspoon fine sea salt

  • for the guacamole (optional):

    • 2
      ripe Hass avocados

    • 2
      teaspoons juice from ½ a juicy lime

    • 1
      tablespoon minced red or sweet onion

    • Fine sea salt and freshly ground black pepper


    Make the roasted shallots and tomatoes: Adjust an oven rack to the lower-middle position and heat the oven to 300 degrees. Peel the shallots and cut them lengthwise into quarters. In a medium bowl, toss the shallots with a teaspoon of the olive oil and season lightly with salt and pepper. Turn them onto a rimmed baking sheet or into a small baking dish and roast, stirring occasionally, until softened and spotty brown, 35 to 40 minutes. Return the shallots to their original bowl.


    While the shallots are roasting, use a sharp paring knife to halve the tomatoes lengthwise. Squeeze the seeds from each half into the sink and drop the halves into a small bowl. Toss the tomatoes with the remaining 1 teaspoon olive oil and season lightly with salt and pepper. When the shallots are roasted and back in their bowl, turn the tomatoes onto the same baking sheet and roast until softened and shriveled, stirring occasionally, about 45 minutes. Remove from the oven and combine with the roasted shallots (fig. 2.1). Set aside.


    Make the pickled jalapeños: While the tomatoes are roasting, pour 1½ cups of the water into a medium mixing bowl. Add 2 teaspoons fine sea salt and stir to dissolve. Slip on the rubber gloves, if using. Trim off and discard the stem ends and tips from the chiles. Working over the sink or a bowl, use an old-fashioned vegetable peeler to core out the ribs and seeds from each chile (fig. 3.1), rendering it a hollow shell (fig. 3.2). Slice the chiles crosswise into ⅛-inch rounds (fig. 3.3), and then drop the slices into the salted water. Let stand for 30 minutes.


    Pour the vinegar and the remaining ½ cup water into a medium nonreactive saucepan. Add the honey, garlic, and ½ teaspoon salt and bring to a simmer over medium-high heat, stirring to dissolve the salt. Simmer for 2 minutes, and then remove the saucepan from the heat. Drain the chiles in a footed colander and stir them into the hot vinegar mixture. Cover the saucepan and let cool to room temperature.


    Make the lime-cilantro cream: While the chiles cool, in a small bowl, combine the crema, lime zest, lime juice, cilantro, and salt and pepper to taste and stir until well mixed. Set aside.


    Make the guacamole: Using a chef’s knife and working one at a time, cut the avocado in half lengthwise, cutting around the pit. Using both hands, twist the 2 halves in opposite directions to loosen (fig. 6.1), and then pull the halves apart. Thrust the base of a blade of a chef’s knife in the avocado pit and twist to extract it. (To remove the pit from the knife blade, knock it off with a wooden spoon.) Using a paring knife, cut the flesh in a ½-inch crosshatch pattern, taking care not to cut through the skin. Use a spoon to scoop the flesh (fig. 6.2) into a small bowl. Repeat with the second avocado. Add the lime juice, onion, and salt and pepper to taste. Stir and mash with a fork until the guacamole is creamy with a few chunky bits of avocado (fig. 6.3). Taste for seasoning, press plastic wrap directly against the surface to prevent discoloration, and set aside.


    Heat a heavy 10-inch square or round griddle, preferably well-seasoned cast-iron, over low heat for 15 minutes. Place the shredded cheese, the roasted shallot-tomato mixture, the pickled jalapeños, lime-cilantro cream, and guacamole nearby.


    To make standard quesadillas: Place a tortilla on the griddle. Sprinkle it evenly with up to ½ cup shredded cheese, and then dot with the roasted shallot-tomato mixture and pickled jalapeños (fig. 8.1). Place a second tortilla on top and press down on it with a spatula to seal (fig. 8.2). Cook until the bottom tortilla is crisp and spotty brown, 2 to 3 minutes. Flip the quesadilla and continue to toast until crisp and spotty brown and the cheese has melted, 2 to 3 minutes longer. Transfer the quesadilla to a cutting board and cut into quarters. Place on an individual plate or plates, dollop the lime-cilantro cream and guacamole on the side, and serve (quesadillas are best eaten hot of the griddle). Repeat with the remaining ingredients.

    To make rolled quesadillas: Place a tortilla on the griddle and sprinkle evenly with ¼ cup shredded cheese, leaving a ½-inch border around the edge. Dot the half nearest you with the roasted shallot-tomato mixture and pickled jalapeños, again leaving a border. Starting from the filled side, roll the tortilla up around the filling (fig. 8.3) and toast the quesadilla seam-side down for 1 to 2 minutes until the seam is sealed. Once sealed, continue to cook, occasionally rolling the quesadilla, until crisp and brown on all sides (fig. 8.4), 3 to 4 minutes. Transfer to an individual plate, dollop the lime-cilantro cream and guacamole on the side, and serve. Repeat with the remaining ingredients.

    1. 2.1
    1. 3.1
    2. 3.2
    3. 3.3
    1. 6.1
    2. 6.2
    3. 6.3
    1. 8.1
    2. 8.2
    3. 8.3
    4. 8.4