Last week I decided I really wanted to make something with caramelized onions. So I thought a bit, searched online for some foods to go with it, and found a couple things that interested me — paring caramelized onions with butternut squash, and using caramelized onions in a tart. So I decided – hey, I’ve never used phyllo dough, that sounds fun! (Later I would reconsider my choice of adjective.) I also decided to add sun-dried tomatoes for tartness, and goat cheese for a savory element.

I always get excited and envision myself easily conjuring up wonderful, gorgeous, complicated meals with with ease. Well, this was another kind of humorous-looking result, but it did taste good. Since taste is always one of my top goals, I considered it a success, albeit one that I won’t be making for dinner guests without a few changes.

For all the lowfattedness (well, it’s a word now!) of phyllo dough, if you prepare it as advised by nearly all recipes, you’ll more than make up for that with the butter and oil you’ll be brushing on each layer. So future phyllo forays will likely include skipping the step of coating each layer with a half-teaspoon of fat.

Ingredients for Butternut Squash, Caramelized Onions, Sundried Tomatoes and Goat Cheese in Phyllo Dough

Ingredients for Butternut Squash, Caramelized Onions, Sun-dried Tomatoes and Goat Cheese in Phyllo Dough (yes, yes, its called fillo dough on the package, but I really prefer phyllo)

I roasted the butternut squash (and some garlic – more about that later). Then I threw it in the food processor, along with several cloves of roasted garlic and a bit of salt, and puréed it. (I got the idea for puréeing it from a lasagna recipe I have with butternut squash, which I adore). So the garlic. Yeah. Apparently throwing garlic cloves in a pan isn’t quite the same as wrapping a whole head of garlic with the skin still on in aluminum foil and roasting it. They get done really quickly when peeled and just sitting individually in the pan. So I ended up roasting two batches – the first time resulted in hard nuggets of brown garlic, and the second resulted in some mostly lovely roasted garlic.

Butternut Squash Ready to Roast

Butternut Squash Ready to Roast

Making caramelized onions is fun. That pretty much sums it up for me. You start with overly powerful, brash, white onions, and you cook and cook and cook, and you end up with these lovely, browned, sweet tasting onions. I used a bit of salt and pepper, a bit of sugar, and deglazed with both balsamic vinegar and water.

Caramelizing the Onions

Caramelizing the Onions

The sun-dried tomatoes I just threw in a mug of stock which I heated up, let them soak, then drained and chopped them up fairly finely.

Then came assembling the whole thing. I followed the advice on the phyllo dough box, thawing it overnight, only taking out the number of sheets I was going to use, covering it with plastic wrap topped with a damp towel. Hearkening back to my earlier cockiness in thinking I could easily whip up a low-fat pie crust, I cringed (and swore) as I picked up the first sheet, then the second sheet, then the third sheet, only to see them break in half and then crumble in front of me. But then I took a deep breath, pretended I was working with Fabergé eggs, and ended up with just an inch and a half crack in the bottom of most of the next eight sheets. I brushed some olive oil on each sheet as I piled them on, then layered the butternut squash, caramelized onions, goat cheese, and tomatoes on top of that.

Assembling the Phyllo Dough Roll

Assembling the Phyllo Dough Roll

Then, going for broke, I rolled the thing up. That actually didn’t go too badly, but I probably should have been closer to the pan for the transfer. I brushed the top with olive oil, then baked it at 325 degrees for 35 minutes or so. Cutting it into four pieces was pretty amusing (pictures at the bottom). But as I said – it tasted quite good!

Huge Phyllo Dough Burrito-Looking Thing

Huge Phyllo Dough Burrito-Looking Thing

Butternut Squash, Caramelized Onions, Sun-dried Tomatoes and Goat Cheese in Phyllo Dough

1 butternut squash (about 1.5 lbs – the picture above is a 3 lb butternut squash – I had leftover squash for 3 days)
1 large white onion
4 oz goat cheese, softened
3 oz package sun-dried tomatoes
phyllo dough (about 8 sheets – you’ll want some spares!)
1 head of garlic
1 Tbsp avocado oil
4 tsp olive oil
4 tsp balsamic vinegar
4 tsp water
1 tsp sugar
1/4 to 1/2 cup vegetable stock or broth (or water)
salt and pepper

Preheat the oven to 400 degrees. Cut the butternut squash in half crosswise, and then cut each half again lengthwise (see picture above). Remove seeds and pulp. Place cut side down on a pan coated with cooking spray. Cut about 1/2 inch off of the top of the had of garlic, wrap it in foil, and add it to the pan with the squash. Bake 35-50 minutes. Check both the squash and the garlic at 35 minutes. The squash is done when a fork easily pierces the skin and flesh).

While the squash and garlic is roasting, cover the sun-dried tomatoes with some vegetable stock, heat in the microwave for a minute, and then let them soak.

Cut the onion into strips about 1/3 inch wide and about 2-3 inches long. Heat the avocado oil in a skillet on medium-high heat, then add the onions, and cook for 5 or so minutes, stirring constantly. Add a couple shakes of salt and grinds of pepper and a teaspoon of sugar. At this point, I turned the heat down to medium, because things started seeming a bit too brown. Continue to cook for 15-20 minutes more, deglazing with balsamic vinegar and/or water as needed (I added a teaspoon of vinegar and a teaspoon of water four times during cooking). Once the onions are a nice brown color (see picture above), tender and sweet, they’re done. Set aside until the rest of the items are ready.

Drain the tomatoes, and then finely chop them. Set aside.

Once the butternut squash is done, remove the shell, then cut the squash into small pieces. Put them in a food processor with 4-6 of the garlic cloves, and puree. Add salt and pepper to taste.

Layer 8 sheets of phyllo dough, brushing each with olive oil before placing the next one on top (I used 4 teaspoons of oil on the 8 sheets plus the top of the roll). Then add the remaining ingredients in the following order: butternut squash, caramelized onions, goat cheese (just rip this into pieces (globs) and spread them out evenly), and tomatoes. Carefully roll it up starting at one of the short ends. Brush the top with oil and bake at 325 degrees for 30-40 minutes.

Slice into equal sizes, laugh at how sloppy it looks, and serve.

A Couple of Views of My Not So Perfectly Formed Phyllo Dough Roll, Sliced

A Couple Views of My Not-So-Perfectly-Formed Phyllo Dough Roll, Sliced

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