Slow-Roasted Pork Shoulder with Stuffed Squash

Slow-roasted pork shoulder of a cutting board being sliced by a person

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.

Slow-Roasted Pork Shoulder with Stuffed Squash

  • Quick Glance
  • (2)
  • 45 M
  • 3 H, 30 M
  • Serves 8
5/5 - 2 reviews
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Special Equipment: Kitchen string


  • For the pork shoulder
  • For the stuffed squash


Roast the pork

Preheat the oven to 400°F (204°C).

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.

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

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.

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

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.

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.

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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Recipe Testers' Reviews

This was perfect for eight people (and we still had some leftovers). It’s easy enough to prepare on a weeknight, and the recipe timing could not be more perfect. The roast was cooked to perfection—juicy, tender, and extremely tasty. I used white wine and the gravy was OUTSTANDING. The rice was also perfect, even though I used butternut squash and this took longer than the 20 minutes in the oven. Truthfully, I would have used more pancetta. This recipe will definitely be a repeat at our home. Everyone was raving about it, and my daughters, who are the most critical of new recipes, absolutely loved it. Yesterday we had the leftovers in sandwiches and they were amazing.

What a lovely recipe for a fall family dinner. A simple roast and winter squash — what could be better? My butcher was sweet enough to debone, tie, and score the shoulder roast as I needed it. Soon the house was filled with the enticing aromas of roasting pork and squash. Since I didn’t have any pancetta, I had to use bacon for the stuffing. Easy to make, stuff and bake. The results were great. As for the roast, I have noticed that in this day and age of lean meats, finding a roast with the fat and rind is not easy, but it is well worth the search. I didn’t have any hard cider, but I did have fresh apple cider form the local orchard and mixed it half and half with a tasty white wine. I only needed about one cup more of the wine/cider mix to finish basting the roast, making three cups in total. I don’t know if my favorite part was the cracklings on roast (a childhood favorite) or the glaze from the wine and cider. There was no need to call anyone a second time for supper. No-one even noticed I had forgotten the pan juices in the kitchen. All in all a great meal. I do think that the stuffed squash would make a fabulous meal in their own right with a salad.

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  1. When I was in my teens and first really got into Chinese cooking, we’d buy a whole pork loin probably twice a month–roast the big end, a meal with chops, and the rest for stir fries, sweet and sour, etc. It always had a nice thick white layer of fat. Gorgeous. Now, not only is it almost impossible to find that kind of pork, it’s gotten difficult to find a whole loin! Boy, can I relate to the wailing over dry pork. This looks lovely, though, and cooked so nice and slow, and that delicious basting liquid. I’ve got a shoulder roast in the freezer. If I can get up the oomph to bone it, I’m going for this. If not, I’ll try it as a braise with the cider/white wine braising liquid. Also, I can see a bunch of small winter squashes, one per person, as a unique side dish. This is definitely a keeper. Thanks for this slideshow!

    1. You’re so very welcome, ruthie. Inspiration finds us everywhere, does it not? Love how you see the world and tweak it to your needs and desires. Can’t wait to hear what you decide to make next…

  2. Delicious recipe and works exactly as written. I served this up for an early Christmas family dinner tonight and everyone raved about it. Can’t wait for leftovers tomorrow!

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