Winter Squash Calzones

October 11, 2010 § 12 Comments

It’s a Monday holiday, which means an already beautifully languorous and relaxed weekend (if you can really call a weekend relaxed when it includes staining a set of cubbies, running a half marathon, going to a parade, and having a dinner party…Hey, that doesn’t sound relaxing at all!! And yet, it was. Something in the air, I think.) is even longer. I think every weekend should be a three day weekend. I’m convinced that it would actually increase everyone’s productivity by oh, at least 5 trillion percent, or so. Saturday allows you to begin to unwind, Sunday allows you to relax and also putter through some odds and ends that need doing, and by Monday you are free to be completely loose and carefree and rejuvinated so that on Tuesday you’re ready to jump back into work. Well, maybe.

Anyway, what I’m dancing around and trying to get at here is that on Monday holidays (however little the person whom the holiday is celebrating actually deserves said veneration, ahem, Columbus didn’t actually discover America, ahem, the Vikings did, ahem. Sorry, something in my throat there.) my mind had reached a state of complete and utter emptiness. Which, I think in Eastern spiritual practices is considered an ultimate goal. In Western practices it’s considered being blonde (hehe, gotta live up to your stereotype sometimes!). And either way, it turns out it makes it very hard to think of something to write, even if you really want to.

Am I allowed to just say these calzones were seriously delicious, you should make them, the end!? Because they were. I think “calzone” might actually be Italian for delicious. Or at least, it should be. Think about it. You take all sorts of delicious seasonal ingredients, add delicious cheeses, stuff it into a delicious dough, and then eat it steamy and crusty and gooey after it comes out of the oven. Overall they’re just a pretty darn good idea. They also make wonderful leftovers for lunch because your food is all neatly wrapped up in a portable little package and they reheat nicely. You can stuff them with whatever vegetables are in season, but even if it weren’t in season I’d say winter squash is one of my very favorite fillings. The combination of warm, sweet squash with pungent, nutty cheese sings songs of fall and coziness and contentment.

When I decide I’m going to make something involving roasted winter squash, I often roast the squash the night before, while I’m making and eating that supper. Then I scrape the cooked squash into a Tupperware while we’re doing dinner clean up and refrigerate it to use the next day. If I determine I’m going to make either calzones or pizza, I usually make the dough for it in the morning, while I’m waiting for my coffee to brew, and let it rise in the refrigerator over the course of the day. That way when I get home and am hungry and not in the mood to wait 2 hours for dough to rise or squash to roast, I don’t have to because they’re already prepared! At this point all that’s required is to mix the squash with some caramelized onion, garlic, and the cheeses – one mild and one potent, it my general rule – and roll out the dough. You can also add other roasted vegetables and spices of course. I considered adding roasted peppers or some spinach and some nutmeg or even tarragon. But, in an Alice Waters moment of wanting to let the squash speak for itself, I decided to let it star on its own. With some salad and maybe a little tomato sauce for dipping your calzone, it’s the sort of meal that makes you feel ridiculously blissful and warm and fuzzy inside. Kind of like a long weekend.

Winter Squash Calzones (serves 4-6)

Dough: (or you can use pre-prepared pizza dough. I won’t tell anyone this time around, I promise)

  • 1 cup warm water (around 90-95F)
  • 1 ½ tsp. active dry yeast
  • 1 Tbs. honey or sugar
  • 1 ½ tsp. salt
  • 2 ½ – 3 cups all purpose flour
  • olive oil


  • Olive oil
  • 1 medium winter squash (I used kabocha, you could also use butternut or pumpkin or buttercup)
  • 1 medium onion, peeled and chopped
  • 1 clove garlic, peeled and minced
  • 1 cup shredded mozzarella or ricotta
  • ¾ cup chevre, or parmesan, or crumbled feta or another pungent cheese
  • about ½ tsp. each salt and pepper
  • tomato sauce for serving, if desired
  1. To make the dough, mix the honey into the warm water, sprinkle the yeast on top and let it sit for about 5 minutes, until the yeast is starting to foam. Stir in the salt and stir in flour a half cup at a time until the dough is thick enough to form into a shaggy ball. Using a floured hand, knead the dough in the bowl for a few minutes, incorporating a little extra flour into the dough if it’s too sticky to handle. Then brush a little olive oil on the dough and cover the bowl with a clean cloth. Either let the dough rise for about 2 hours in a warm place, or place in the refrigerator and allow to rise for 8-12 hours (or even longer is fine). If you have let the dough rise in the refrigerator, take it out and let it sit at room temperature for about half an hour before baking with it.
  2. To prepare the filling, first roast the squash by cutting it in half, scooping out the seeds, rubbing it with a small amount of olive oil and baking it, cut sides down on a baking sheet, in the oven at 425 until it soft and easily pierced by a fork (the time for this varies by squash, but it’s generally around an hour). Allow the squash to cool enough to handle, then scoop the flesh out into a bowl (or storage container if you’re doing this step ahead of time).
  3. In a large frying pan, heat about a Tbs. of olive oil over medium-low heat. Add the chopped onion and cook, stirring occasionally for about 8 minutes, until getting nicely browned, then add the garlic and cook for another 2 minutes. If your squash is cold, stir it in as well and allow it to heat for a few minutes. In a large bowl, mix together the squash, onions, and cheeses until well combined.  Add salt and pepper to taste.
  4. Heat your oven to 450F. Punch down your dough, and using floured hands, divide the dough into 4 or 6 equal pieces (depending on if you’d like slightly larger or smaller calzones). On a floured surface, roll each piece out into a circle about ¼ inch thick. Place about ¾ cup of the filling on one half of each circle, leaving about ½ inch edge around it. Use wet fingers to moisten the edge of the dough circle then fold the empty side over the top to form a half circle shaped pocket and either crimp the edges with a fork or use your fingers to press them together and roll them inward just a little into a rolled edge. Use a fork to make some little pricks in the surface of the dough.
  5. Repeat with the rest of the dough circles. Arrange the calzones on a lightly oiled baking sheet and bake for 15-20 minutes until golden and lightly browned. If desired, brush each with a little olive oil or melted before during the last 5 minutes of baking to make them extra golden brown. Remove from the oven and allow to cool for 5-10 minutes before serving. Serve accompanied by some warmed tomato sauce, if desired.

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