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Slow-Roasted Pork Shoulder with Stuffed Squash

A roast can seem dauntingly expensive if you’re trying to feed a crowd. But slow-roasted pork shoulder is one of the most satisfying dishes–so tender and, relatively, very cheap. It also looks magnificent. You can vary the stuffing by using dried fruit instead of mushrooms, or add grated Parmesan or wilted spinach.–Diana Henry

LC Back in the Day... Note

Once upon a time, pork roasts came with a lovely gilding of fat, both marbled throughout the meat and also a pure white layer an inch thick (or more). Savvy home cooks across the land knew that this fat cushioned the underlying pork from a hot oven and bathed it during the long, slow roasting time required to coax the cheap cut of meat to supple, tender doneness. Pork such as this was beauteous to behold–and obscenely satiating to consume. Then for seemingly no reason a darkness came across the land. People were afflicted with an obsessive and woefully misguided fear of fat. Pork was bred to contain less fat, and what fat did remain–ravishing, flavorful layers of fat above the lean meat and beneath the skin– was hacked off, oh horror of horrors, by butchers who feared customers would shudder at the site of it. People settled for bland pork that barely resembled its former self and sadness reigned throughout the land over this bizarre behavior fueled by needless, self-inflicted guilt.

This recipe is best honored by that relic, a proper cut of pork—a fatty fat fat pork roast with that stunning white sheath of fatty goodness beneath the skin that can sometimes still be found via diligent searching at meat cases and butcher shops. As for this tale, its ending is a supple fall-off-the-bone pork experience napped with a faintly apple-y, somewhat sweet sauce made from cider and the fatty fat fat drippings from that roast. Don’t forget to thank your butcher kindly.

Special Equipment: Kitchen string

Slow-Roasted Pork Shoulder with Stuffed Squash Recipe

  • Quick Glance
  • 45 M
  • 3 H, 30 M
  • Serves 8

Ingredients

  • For the pork shoulder
  • 6 pound boneless pork shoulder roast (the fattiest one you can find–trust us, it’s worth making a special request from your butcher) rind scored
  • Sea salt and freshly cracked black pepper
  • 1/4 cup mild olive oil
  • 4 1/2 cups hard cider or white wine
  • For the stuffed squash
  • 2 small winter squash, such as butternut or acorn
  • 4 tablespoons butter
  • 1 smallish onion, finely chopped
  • 3 ounces pancetta or bacon, chopped
  • 8 ounces mushrooms, stems removed, caps quartered
  • 1 cup long-grain rice, preferably a mix of brown rice and wild rice
  • 2 1/4 cups chicken stock or water

Directions

  • Roast the pork
  • 1. Preheat the oven to 400°F (204°C).
  • 2. Place the pork flat on your work surface and season it with salt and pepper. Roll it up tightly and tie it at 1-inch intervals with kitchen string. Rub the entire surface of the pork with the oil and season it again with salt and pepper. Place in a roasting pan, fatty side up. Roast the pork, uncovered, for 25 minutes.
  • 3. Reduce the oven temperature to 325°F (163°C). Pour 2 cups hard cider or wine into the roasting pan. Roast the pork, uncovered, for another 25 minutes per pound (not including the initial 25 minutes), basting the pork with the pan juices and gradually adding 2 more cups of the cider or wine to the roasting pan. This will take about 2 1/2 hours, depending on the size of your pork roast.
  • Make the squash
  • 4. While the pork roasts, halve the winter squash lengthwise and scoop out the fibers and seeds. Score the cut sides with a sharp knife. Place in a roasting pan, cut side up, and smear the surface of each with 1 tablespoon of the butter. Season and roast at 325°F until softened, about 45 minutes. Remove from the oven.
  • 5. Melt another 1 tablespoon of the butter in a saucepan and sauté the onion until quite soft. Add the pancetta, mushrooms, and remaining butter, and sauté until colored. Stir in the rice to coat, season with salt and pepper, and add the stock or water. Cover, bring to a boil, reduce the heat to low, and cook until tender, 20 to 30 minutes or so. Remove from the heat and set aside.
  • Place the finishing touches on the pork and squash
  • 6. When the pork is cooked through—that is to say, when the meat is fork-tender and no trace of pink remains in the meat–place it on a platter. Cover loosely with foil and let rest for 30 minutes.
  • 7. Increase the oven temperature to 375°F (190°C). Spoon the rice stuffing into the winter squash cavities, mixing it with the butter that has collected there. Place in the oven for 30 minutes to warm. The squash should be completely tender and the top should be golden.
  • 8. Pour the cooking juices from the pork into a fat separator or a pitcher and pour or skim off the fat that collects at the top. Deglaze the roasting pan with the remaining 1/2 cup hard cider or white wine, stirring constantly. Add the defatted pork juices and let it bubble away until you have a thin, tasty gravy. Taste and adjust the seasonings accordingly. Serve the pork alongside the squash and pass the gravy on the side.
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