Roast Turkey with Challah Stuffing, Roasted Grape and Chestnut Gravy

Preparation info

  • Difficulty


  • Yield:

    8 to 10


Appears in

Purim food metaphors are pretty straightforward. We eat grains and legumes because that’s what Queen Esther did; in devouring pastries shaped like various parts of Haman, we swallow up our enemy; sweets are the taste of victory over forces that sought to destroy us.

But how did turkey, a bird that began in North America, become a symbol of King Ahasuerus of Persia?

His “bird brain” is one answer. While the chicken is no rocket scientist, the turkey has a reputation as a particularly foolish animal, and so is a fitting stand-in for a king who was duped by his vizier and played the fool in humiliating his first wife, Vashti, in front of his friends. Besides, Ahasuerus ruled over a kingdom that stretched mi Hodu ad Kush (from India to Ethiopia), and the bird is known in Hebrew as tamegol Hodu (Indian chicken; as yet, we eat no Purim foods associated with Ethiopia) because it was thought to have originated in the subcontinent. (In fact, that error has been the source of controversy among some ultra-Orthodox Jews regarding the kosher status of turkey. Because not all the prohibited birds listed in Leviticus could be translated, the custom arose to eat only birds that Jews had a tradition of eating. Believing that Indian Jews had dined on the bird for centuries, the sages deemed it kosher. Of course, the only people who had a tradition of turkey dinner were the unquestionably non-Jewish Native Americans.)

For cooks, though, the problem with turkey is not its feeble brain, but its dry, rather bland flesh. In this recipe I use several techniques to produce an exceptionally moist and succulent bird—most importantly, rubbing a savory flavor paste made with challah under the skin. The bread acts like a damp sponge, continuously replenishing the meat with herby seasoning and moisture. And, separated slightly from the flesh, the skin bronzes and crisps up beautifully.

The rest of the challah loaf becomes a magnificent stuffing for the body and neck cavities. Feel free to eliminate the stuffing if you must cut down on preparation time, but I urge you to try the flavor paste: it’s simple and quick and makes a real difference. (If you do omit the stuffing, decrease the final cooking hour by 2 to 3 minutes per pound.)

There’s no need to prepare a giblet stock or roux for the luscious gravy: its intense flavor and thickening come from the black grapes roasted along with the bird and pureed chestnuts, mingled with the pan juices.

Enjoy this special turkey not just on Purim but Thanksgiving and the Jewish fall holidays as well.

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  • 1 small loaf challah (about ¾ pound), to be divided for the flavor paste and stuffing
  • One 12- to 14-pound fresh-killed turkey
  • 3 to 4 cups chicken broth, preferably homemade or good-quality, low-sodium purchased
  • 1 cup whole black or Concord grapes
  • 2 tablespoons pomegranate molasses
  • Additional grape clusters or herb sprigs, for garnish

For the Flavor Paste

  • ¾ cup mild olive oil
  • cup coarsely chopped garlic (6 to 9 fat cloves)
  • 3 tablespoons fresh lemon juice
  • 3 tablespoons chopped fresh rosemary leaves
  • 2 tablespoons chopped fresh thyme leaves
  • 2 cups toasted challah cubes (from the challah loaf)
  • Salt and freshly ground black pepper

For the Stuffing

  • cup mild olive oil
  • 4 cups chopped onion
  • 1 cup thinly sliced leeks (white and pale green parts only)
  • Salt and freshly ground black pepper
  • 1 tablespoon plus
  • 2 teaspoons balsamic or sherry vinegar
  • 1 teaspoon sweet paprika, preferably smoked
  • Remaining bread cubes from the challah loaf
  • 2 tablespoons plus
  • 2 teaspoons finely chopped fresh sage
  • 1 tablespoon plus
  • 1 teaspoon finely chopped fresh rosemary leaves
  • 1 tablespoon plus
  • 1 teaspoon finely chopped thyme leaves
  • 1 cup chicken broth
  • 1 large egg, beaten

For the Gravy

  • 1 cup coarsely chopped shallots
  • 2 tablespoons mild olive oil
  • ¾ cup coarsely chopped garlic
  • Salt and freshly ground black pepper
  • cups whole chestnuts, cooked and peeled (frozen, vacuum-packed, jarred or canned are fine for peeling raw chestnuts, then simmer the shelled nuts in water until tender)
  • 3 tablespoons Marsala or Cognac
  • 3 cups chicken broth
  • ½ cup black or Concord grapes, halved and pitted
  • 1 teaspoon chopped fresh rosemary leaves
  • 1 teaspoon chopped fresh thyme leaves


Preheat the oven to 325°F. Slice the bread and tear or cut it into 1-inch cubes. Spread the cubes out on a large, rimmed baking sheet and toast, shaking the pan occasionally, for about 25 minutes, until dry and crisp. If necessary, use two pans or work in batches. Turn off the oven for now.

Measure out about 2 cups packed of the toasted challah cubes for the flavor paste; put the remaining cubes into a large bowl for the stuffing.

Make the flavor paste: combine the oil, garlic, lemon juice, rosemary, and thyme in a food processor, and process to a coarse puree. Add the reserved 2 cups toasted challah cubes and process until smooth. Taste and add salt and pepper as needed. Transfer the flavor paste to a bowl.

Prepare the turkey: remove the neck, wingtips, and giblets and reserve for stock or discard. Reserve the liver for chopped liver or broil later for cook’s perk. Remove all visible fat. Separate the skin from the body: Starting at the neck end, gently loosen the skin by sliding your hand underneath the breast and working your way back to the thighs and drumsticks, being careful not to tear the skin. With a tweezer, pull out any quills or pinfeathers left in the turkey skin. Rinse the turkey well, inside and out, and pat it dry. Spoon half the flavor paste under the turkey skin, using your fingers to push it all over the breast and down the drumsticks. Rub all but 3 tablespoons of the remaining flavor paste inside the turkey cavity and over the surface of the bird. Set the turkey breast side down on a V-shaped rack in a roasting pan. Let the flavor paste permeate the meat while you make the stuffing. (If you want to get a headstart—and let the flavor paste perfume the turkey more deeply—slip the bird into a very large plastic bag, tie the bag securely, and refrigerate for up to 48 hours.)

Preheat the oven to 450°F and remove the top rack, if necessary. If you have refrigerated the seasoned turkey, bring it to room temperature.

Start the stuffing: in a 12-inch heavy skillet, warm the olive oil over medium-high heat. Add the onion and leeks, sprinkle with salt and pepper, and stir to coat with the oil. Sauté, stirring, for 3 minutes. Cover, turn the heat down to low, and continue cooking, stirring occasionally, for about 30 minutes, until the vegetables are quite soft. Add the vinegar, raise the heat to high, and boil, uncovered, until the pan liquid is evaporated. Add the paprika, and sauté, stirring, for about 5 minutes, until the mixture begins to brown and the oil separates slightly from the rest of the ingredients. Transfer the mixture to the bowl of reserved challah cubes. Add 2 tablespoons of the sage, 1 tablespoon of the rosemary, 1 tablespoon of the thyme, and the broth, and blend well. Season to taste with salt and pepper. Add the egg and combine well.

Loosely pack the body and neck cavities of the turkey with the stuffing. Fasten the cavities closed: I enlist someone to help, pulling the loose skin over the neck cavity and holding the drumsticks together while I truss and tie up the bird. If you prefer, use turkey lacers or metal skewers. Don’t overstuff the bird; cook any remaining stuffing later, moistened with some of the pan juices, in a greased baking dish for about 25 minutes at 350°F, until lightly browned on top and completely cooked through.

Pour 2 cups broth into the roasting pan. Roast the turkey, breast-side down on the rack, for 40 minutes. Turn the turkey breast-side up and continue roasting for 20 minutes.

Reduce the oven to 325°F. Baste generously with pan juices. Cover the breast with foil (to slow down the cooking of this more delicate section, which otherwise would be overcooked by the time the rest of the bird is done). Add 1 cup broth to the pan. Roast 1 hour more, basting all over (including the breast beneath the foil) occasionally.

Add the whole grapes to the roasting pan, and discard the foil covering the breast. If needed, add another cup of broth to the pan. Mix the pomegranate molasses with the remaining flavor paste and brush half of it all over the bird. Baste one more time with the pan juices, and continue roasting until the juices run clear, and a thermometer inserted in the thickest part of the thigh registers 170°F, about 1 hour longer (the temperature will rise about ten more degrees while the turkey rests). Brush with the rest of the flavor paste-pomegranate mixture once during this final roasting, but do not baste again.

About 15 minutes before the turkey has finished roasting, start the gravy base: in a large, heavy, deep skillet, sauté the shallots in the oil over medium heat for about 3 minutes. Add the garlic, sprinkle lightly with salt and pepper, and continue cooking, stirring occasionally, until softened but not browned. Add 1 cup of the chestnuts and cook for 2 minutes. Add the Marsala or Cognac, raise the heat to high, and bring to a boil, stirring to blend the flavors. When the Marsala has evaporated, turn off the heat and set aside until you have strained and defatted the pan juices.

Remove the turkey to a carving board. Scoop out the stuffing, place it in an oiled baking pan, and stir in the remaining stuffing herbs: 2 teaspoons sage and 1 teaspoon each rosemary and thyme. Turn the oven to 350°F. Bake the stuffing until lightly browned on top (this will eliminate any excess wetness from basting and keep the stuffing hot). Tent the bird loosely with foil and let it rest while you finish the gravy.

Pour the contents of the roasting pan (including the roasted grapes) into a fine-mesh sieve set over a large bowl. Using a wooden spoon, press down hard on the solids to extract as much liquid and flavorful grape puree as possible, making sure that any grape seeds are trapped in the sieve. Discard the solids. Remove as much fat as you can from the pan juices in the bowl.

Transfer the defatted pan juices to the gravy base in the skillet, and add the 3 cups broth. Cook, stirring occasionally, over medium-high heat for 15 minutes to marry the flavors. Let cool slightly, then using a slotted spoon, transfer the solids to a food processor or blender. Add some of the pan liquid and puree, in batches, if necessary, until smooth. Return the pureed mixture to the skillet and bring to a simmer. Stir in the remaining chestnuts, grapes, and herbs, and heat until piping hot. Taste and correct the seasoning. If the gravy is not as thick as you would like, raise the heat, and cook uncovered until reduced to the desired consistency.

Carve the turkey and decorate the platter with the grape clusters and herb sprigs. Pass the stuffing and the gravy boat separately.