Acorn and Butternut Squash Pie with Bourbon Whipped Cream

On Saturday I went to my first Chicago Women Cooks-in-Training meetup. I discovered the group through A., a girl I met at my first Spanish meetup, who explained that the group was a bunch of women who were interested in learning to cook. I consider myself a semi-decent cook already, but I’m always down for learning more and sharing dishes with others. The theme for this particular meeting was autumn fruits and vegetables, a celebration of all the wonderful produce that comes at end of the summer season. Once I saw the theme I knew exactly what I would make: an acorn and butternut squash pie.

Now, have you ever made an acorn and butternut squash pie, you may ask? The answer would be no. But wait, have you ever even tried acorn squash, you may also ask? Again, the answer would be no. But how different could the two winter squashes be from pumpkin? Not that I’ve ever made a pumpkin pie, either, but I’ve seen my mother do it a thousand times. And I’ve heard much about how sweet acorn squash can be, so I figured it would probably pair well with the butternut, which I already know and love. And to top it off, I’d make bourbon whipped cream. The idea seemed simple enough to me.

The basis of the pie was JoC’s recipe for pumpkin pie. The first step was to make the crust, which I’ve made before and still have some issues making. Mainly, I can’t seem to roll out the crust evenly. I dealt with this by cutting off some of the thicker part and putting it behind the thinner parts to create the fluted edge (the edge was done just by pressing in on one side with a knuckle and pressing out on the other side with two knuckles). The instructions then said to brush the crust with some egg yolk, then follow the general instructions for pre-baking crusts, which are to dock it with a fork, cover it with foil, and weigh it down with beans or pie weights. I’ve seen this method on TV before, but I thought it was odd that I was being told to brush the pie with the yolk prior to covering it with foil. How would that allow the crust to brown and wouldn’t the yolk just stick to the foil? Yeah…those ended up being good questions because the crust did not, in fact, brown and it did, in fact, stick to the foil. I was sorrowed by the thin layer of what should have been crispy crust adhering fervently to the foil. 

Beautiful, golden, yolkiness that could have been all over my crust

Sigh. But, oh well—that part would be covered by the filling anyway. I had already baked the two squash and run the flesh through my potato ricer (I think the texture you get using a ricer is much smoother than what you get just using a masher). It was at that point that I took my first taste of acorn squash, which I can only say made me a little weak in the knees. It was so good, so sweet, so freakin’ wonderful. Why have I never had acorn squash before? Lord. One cup of the mashed acorn squash met one cup of the mashed butternut squash, joined by a couple eggs, some brown sugar, some white sugar, and some heavy cream. The spices were your standard cinnamon, ginger, nutmeg, and allspice. 

Baked acorn squash

Acorn squash puree

Baked, seeded butternut squash

Butternut squash puree

Upon pouring the filling into the baked crust, I noticed that it seemed like it would be too much. I filled it almost to the top, let it settle, then decided I could fit the remaining filling in. And fit it did, but when I picked up the pie to put it into the oven, the filling sloshed over the crust and started dripping down the foil guards I had placed around the edges. Even worse, once I set the pie in the oven, the rack tilted a little and a little bit of the filling spilled out onto the oven floor. With some quick maneuvering, I managed to put a cookie sheet underneath the pie to catch the drips and wipe up the filling with a paper towel before it started to burn. And I only touched bare skin to oven wall once—pretty good for averting disaster if you ask me.

The pie took forever to bake. It was at least 30 minutes past the suggested baking time before the center stopped trembling whenever I pulled out the rack to check on it. There was definitely too much filling in there and the liquid that had spilled over the crust resulted in a lovely blackened hue. Yeah, it burned. 

 It wasn’t pretty, but it smelled good, and it seemed a shame to waste it. I had planned to make bourbon whipped cream to accompany the pie, so I said to myself: Here’s what we’re going to do. We’re going to pipe whipped cream over the top and no one will ever know. 

And that’s just what I did. I had planned to make the whipped cream at A.’s place since I was going to the Spanish meetup first and couldn’t have whipped cream sitting out for that long. With a fifth of Jack Daniels in my bag, some sugar, a measuring spoon, and my giant star tip, I picked up a half-pint of cream at Jewel before heading over to A.’s where I proceeded to “photoshop” my pie. In the rush to get everything together for the meetup, I forgot to put my camera in my bag so I wasn’t able to get a good shot of the final pie, but you can see it in the group photo below.

That's mine on the left, all covered in whipped cream.

Apparently my photoshop skills were so great that when I introduced myself and my pie, I heard one girl comment that she’d thought it was store-bought. Truthfully, though, piping that whipped cream was the easiest thing I’d done through the entire pie-making process.

But, how did it taste? Fantastic. Fluffy, subtly flavored by the two squashes, and topped by the not-overly-sweet whipped cream with just a hint of the bourbon kick, it was easily one of the best things I’ve ever made. This was a great idea.

Even though this pie wasn’t a 100% success, I decided to share it anyway because I think an important part of any type of cooking is knowing that not everything turns out right the first time you try it. Hell, sometimes things don’t turn out right the tenth or the fiftieth time you make it. What’s important is that you learn from your mistakes and try it again. There were two main things that went wrong here. 1) I thought it was odd to brush the crust with egg yolk, then cover it with foil, yet I did it anyway and ended up with a less than crispy, browned crust. 2) It seemed like there was too much filling to pour into the crust, yet I DID IT ANYWAY, and ended up with ridiculously long baking time and a burned crust. The upside is that these are mistakes I now know not to commit when I make another pie of this nature again; I couldn’t have figured these things out without trying to make the pie.

There are two morals to the story here. 1) Trust your instincts when baking. They probably won’t do you wrong. 2) Don’t be afraid to try new things and share them with others. Not everything will turn out perfectly, but sometimes you just may surprise yourself.