I first got this idea from Epicurious, who got it from the book Passionate Vegetarian. I also like that this recipe can be made vegetarian or even vegan (use vegetable oil instead of butter, and check that your wine and bread are vegan.) and gives you a centerpiece dish that's accessible to everyone. Keep in mind that this recipe is a ratio, but the amount of stuffing you will need depends largely on the size or number of squash.
This is one of those dishes that sounds more complicated than it actually is; really, the major work is prepping the pumpkin which you do every year for Halloween! I did a lot of the initial prep work, as it's a multi-step recipe and that can be a bit much for a novice cook. First, the bread. I like to buy a loaf of whole-grain French or Italian-style country bread, one that has big holes and a lot of chew - this year I was lucky to find that our local baker had Miche, a large whole-grain sourdough loaf that worked especially well; I used a quarter for this recipe. I removed the crust and cut it into large squares and put it in a 200 degree oven for about 20 minutes, until they were nicely dry and a bit hard.
Next, prepare your squash. If you have room to refrigerate it, you can do this a day ahead (and you can prep all your ingredients ahead and assemble them just before baking,) but it's best to parbake the squash while you're assembling your stuffing. Cut the top off so you have a "lid," and then scoop out the seeds (we usually discard them, but they can be fried or baked if you like.) Place the whole thing on a cookie sheet and set it in a 375 degree oven for about 30 minutes, or until it just starts to cook and your lid is nice and brown (you can put the lid in the fridge after this point and reheat it later.)
Ingredients:
1 large squash
1 loaf wholegrain Italian or French bread, crusts removed, cubed, and dried
2 leeks
2 ribs celery
2 firm sweet-tart apples (fuji, macintosh, cortland, gala, braeburn)
1/3 cup mixed dried cranberries, cherries, and chopped dried apricots
1/3 cup sherry or port
1 medium onion, diced
1/4 cup whole pecans or walnuts
3 tbsp chopped fresh herbs (I use parsley, sage, rosemary and thyme and not just because I'm a fan of Simon & Garfunkel. About 2:1 parsley to other herbs)
1/2 cup apple cider
1/2 cup white wine
1 cup stock (vegetable or turkey, as desired)
4 tbsp light-tasting vegetable oil or butter, as desired
Salt to taste (at least 2 tsp)
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So, Sparky cleaned and diced the celery and leeks, both of which tend to get a little sandy in between the layers and thus need to be washed thoroughly. With both of them, you cut the root end to release the layers. The tough green parts of the leeks are cut off (we slice these off at an angle, because the center light-green parts are tasty) and then they're cut in half and rinsed carefully in between the leaves. Celery stalks are rinsed - and leaves are carefully hoarded for this dish! Both celery and leeks were coarsly chopped and set aside in our largest bowl. Preheat your oven to 375 degrees.
Then the apples were peeled and diced and set aside in a bowl of acidulated (a splash of vinegar, lemon, or other acid added) water.
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The whole thing gets packed into your pumpkin; it's best if you have the pumpkin sitting on a bit of parchment in a large baking dish that can double as a serving dish - sometimes it gets a bit, well, squashy. You want the stuffing to be firm, so that everything is in contact without air gaps, but not so tight that you won't be able to get a spoon in there to scoop it out.
Bake it, uncovered, at 375 degrees for about 40 minutes, or until your pumpkin appears to be about to collapse (you can use your meat thermometer to make sure the center of the stuffing - optimally, it should reach 165 degrees.) You may want to reheat the pumpkin lid for the last 10 minutes of cooking.
You should have a delightfully crunchy top and delicious stuffing that can be served with scoops, or even wedges, of pumpkin flesh. Mmmm.
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