Back when we lived in Los Angeles, I’d tried growing squash in the backyard of our bungalow on multiple occasions. I’m not sure if it was the excessive heat or the soil quality, but they’d get a few feet long and then their leaves would become covered with a pale white powdery mildew and they’d never even get a little squash blossom, let along produce actual squash. So this past spring when I started my seeds for the garden, I decided to only try growing one squash variety since I was used to them failing so often and didn’t want to waste my time and effort. I ended up planting two squash plants from the same heirloom greek variety, and went into it with pretty much no expectations at all. A lot of my heirloom melons succumbed to a powdery mildew really quickly (I think I planted them too early), but surprisingly, the squash hung in there. And then they started to grow, a lot. Then some little squash appeared, and then more squash. At this point, I’ve harvested over 100 pounds of squash from the two plants and there are *still* more baby squash growing on the vines.
Winter Squash Filo Spiral by Eva Kosmas Flores | Adventures in Cooking

 

Winter Squash Filo Spiral by Eva Kosmas Flores | Adventures in Cooking

So with this slightly absurd abundance of winter squash, I decided to make a little fall dessert. Years ago my dad told me about this recipe my yiayia used to make with squash that involved stuffing filo dough with sweetened pumpkin and cinnamon and then folding it into a spiral. I decided to give it a go and see if I could make something similar. The filling here is very simple, just pureed roasted squash, sugar, cinnamon, and a dash of vanilla extract. For the filo, I decided to keep it traditional and used olive oil instead of butter for the brushing. I’d never brushed filo with olive oil instead of butter before, but I am officially a convert. Filo pastries can come out really greasy and heavy with brushed butter, but using olive oil kept the filo really light and crisp as it baked, while still providing it with the fat it needed for flavor and to bind the sheets together.

Winter Squash Filo Spiral by Eva Kosmas Flores | Adventures in Cooking

Like grapes are for wine, different varieties of olives will result in vastly different flavors of olive oil. I used California Olive Ranch’s Arbequina olive oil, it is a very mild and silky oil that’s incredibly buttery in flavor and works perfectly in desserts. I actually reached out to them this year to be their blog ambassador because I am a *huge* fan of their olive oil, so I’ll be posting three more recipes with their tasty stuff next year, too. When I’m cooking with olive oil, purity is a big deal. I want to know that the stuff I’m using is 100% pure extra virgin olive oil, both for flavor purposes and for health reasons, and the thing is that a lot of the “olive oil” that’s brought in from Europe doesn’t have as stringent of standards as the USDA on the percentage of “olive” oil that has to actually be from, you know, olives. So a lot of these imported EVOOs are actually diluted with non-olive vegetable oils, whereas when I use the olive oil from California Olive Ranch, I know I’m getting pure delicious olive oil. The olives they use are non-GMO, and they also have the harvest date of the olives on the bottle so you can be certain of the oil’s freshness. It’s kind of shocking when you compare the difference in flavor between quality EVOO and some of the off brand oils. I’d definitely recommend doing a little taste test sometime, comparing California Olive Ranch olive varietals with whatever you might currently have in your pantry. Delicious, and educational! Also, make sure to store your EVOO in a cool and dark place (like a cupboard) and place the cap back on the bottle as soon as you’re done to keep it tasting fresh; sunlight and oxygen exposure are the two biggest enemies of tasty olive oil.

Winter Squash Filo Spiral by Eva Kosmas Flores | Adventures in Cooking

So, I know the filo spiral looks kind of intimidating. But I promise it is simpler than it looks! You basically just layer a few brushed sheets of filo dough, spread some filling in a line along one side, roll it up into a long tube, and then place the tube in a circular pan, bending it as necessary in places to shape it into a spiral. Just keep repeating this, and there you have it! A beautiful spiral-shaped pastry that tastes insanely good while staying really light and healthy. With no eggs and no butter, I accidentally made a vegan dessert. It isn’t what I set out to do, but it just kind of happened, and honestly if I were to blind taste it I never would guess that it didn’t have any dairy or eggs in it. It just tastes friggin’ delicious. Not to say that vegan desserts don’t taste good (I’ve had a lot of great vegan sweets), but sometimes they don’t measure up to their non-vegan counterparts. But I can say with certainty that here, this is definitely not the case, and it in fact tastes better than if I’d made it non-vegan because the butter would have made it greasy and heavy, and any eggs in the filling would have thinned it out too much to be spreadable (I know this because I originally made a filling with eggs in it, and it came out waaaaay too thin to actually be able to use. Hence the egg shells in some of the photos). It’s the perfect balance of sweet, creamy, comforting, and flakey, and I’m definitely going to be making it again with my dozens of pounds of squash.Like what you see? Pinch pots, panlinen, pastry slab.

Winter Squash Filo Spiral by Eva Kosmas Flores | Adventures in Cooking

Winter Squash Filo Spiral

Author Eva Kosmas Flores

Ingredients

  • 2 cups pureed roasted winter squash or canned pumpkin
  • 1 cup plus 2 tablespoons granulated sugar
  • 1 teaspoon ground cinnamon
  • 1/4 teaspoon vanilla extract
  • 1 lb filo dough thawed if frozen
  • 3/4 to 1 cup California Olive Ranch Arbequina olive oil

Instructions

  1. Preheat the oven to 375 degrees Fahrenheit. For the filling, mix together the squash, 1 cup sugar, cinnamon, and vanilla extract in a medium bowl until smooth. Set aside.
  2. Lightly grease a round baking pan or Dutch oven that’s roughly 10 to 12 inches in diameter and set it aside. When you’ve opened the air-tight package of the filo, lay it flat on a clean working surface and cover it with a clean kitchen towel. Each time you grab a sheet of filo from the pile, make sure to cover the pile with the kitchen towel, otherwise it will dry out very quickly, crumble around the edges, and become impossible to work with.
  3. On a clean flat working surface, lay out one sheet of the filo dough and lightly brush it with olive oil, brushing all the day to the edges. Lay another sheet on top of it, and lightly brush it with olive oil as well. Repeat 4 more times, so you have 6 sheets of filo dough on top of each other. Take a large spoonful of the filling and empty it about 1-inch from the edge of one of the long sides of the filo in a straight line that’s about 1-inch wide and begins and ends about 1-inch from the edge of the dough, refilling the spoon with the filling as necessary to make the complete line. Take the edge of the filo closest to the filling line and roll it over the filling, taking care to keep the filling inside. Keep rolling it until all the filo is rolled up and you have a long cylinder of stuffing. Place the cylinder in the pan, bending it as necessary to shape it to the circular edge of the pan. Brush the placed cylinder with olive oil.
  4. Repeat this process again so you have another cylinder of stuffing wrapped in filo, and line up the end of this cylinder with the end of the last one, forming a spiral shape in the pan. Brush the placed cylinder with olive oil. Repeat until you have filled up the pan with the stuffed filo cylinders and created a spiral, which will take about 4 to 6 stuffed cylinders total.
  5. Sprinkle the remaining 2 tablespoons of sugar over the pan. Place the pan in the oven and bake until the filo turns golden and smells very aromatic, about 35 to 45 minutes. Remove from the oven and allow to cool for 20 minutes before slicing and serving.

 

Winter Squash Filo Spiral by Eva Kosmas Flores | Adventures in Cooking

 

Winter Squash Filo Spiral by Eva Kosmas Flores | Adventures in Cooking
Winter Squash Filo Spiral by Eva Kosmas Flores | Adventures in Cooking
Winter Squash Filo Spiral by Eva Kosmas Flores | Adventures in Cooking
Winter Squash Filo Spiral by Eva Kosmas Flores | Adventures in Cooking

 

Winter Squash Filo Spiral by Eva Kosmas Flores | Adventures in Cooking

 

Winter Squash Filo Spiral by Eva Kosmas Flores | Adventures in Cooking

 

Winter Squash Filo Spiral by Eva Kosmas Flores | Adventures in Cooking
Winter Squash Filo Spiral by Eva Kosmas Flores | Adventures in Cooking

 

 

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