Roasted Garlic and Acorn Squash Strudel

I have been looking for the perfect opportunity to try this recipe for a while now and it finally came.  My inlaws were coming for dinner and they are always up for trying something new. They also don't mind keeping the little one entertained while I work in the kitchen.  Plus they were the ones who grew the squash I used.
This recipe will be a fall staple for me in the future I am sure, especially in years where I have a lot of squash to use up.  I will likely double the recipe and freeze half of the filling for later because it will not add much extra time.  The time consuming part of this recipe is preparing the phyllo for the filling to go into.  Depending on how patient you are and how flakey you like your strudels will be the main determinate in how long the last step takes you.
It is a very versatile strudel that could be use for many different purposes depending on the portion size.  This recipe could easily be adapted to use different types of squash or different spices.

Roasted Garlic and Acorn Squash Strudel

1 head roasted garlic

2 small acorn squash

olive oil

salt and pepper

1/4 cup fresh chopped sage leaves

1/4 tsp grated nutmeg

1 cup ricotta

1/3 cup toasted pine nuts

1/2 box phyllo dough, thawed

1 tbsp butter

3 tbsp olive oil

1. Preheat the oven to 350.  
2. Cut and gut the squash. Place in a baking dish cut side up and sprinkle with olive oil, salt and pepper. Have a quarter inch of water in the dish to help prevent the squash from drying out.  Bake for about an hour or until the squash flesh is cooked through (You can roast the garlic at the same time as you bake the squash).
3. Scrape the insides of the acorn squash out with a fork and mash it well with a fork.
4. Squeeze the garlic cloves out of the paper into a bowl and mash it with a fork.  
5. Place in a frying pan over medium heat and add the sage leaves.  Fry until fragrant and then add the squash.  Once this mixture is cooked through set it aside to cool slightly.
6. In a bowl, combine the squash mixture, nutmeg ricotta and pine nuts.  Stir well and add additional seasoning if desired.
7. Preheat the oven to 400. 
8. Melt the butter and olive oil together.  On a clean working surface lay out your first sheet of phyllo and brush the butter mixture over it.  Alternate the phyllo and butter mixture until you have about 10 layers.  
9. Spread roughly a third of the squash mixture into the centre of the phyllo.  Make sure to leave about an inch on the edges.  Then roll up from the long side and tuck the ends in.  Transfer onto the baking sheet and repeat with the other two.
10. Bake for 20 minutes or until they are golden and crispy.