Jelly Toast

chocolate harvest pie

Okay. I am going to warn you now that I have a little obsession fascination with winter squash. You may laugh or think that I’m overstating, but in my house Fall brings with it some widely mixed emotions. It goes a little something like this:

Me: Woo Hoo! Fall is here, baby!! (usually shouted between sips of hot apple cider and multiple fist pumps).

My husband: Please don’t make squash every night. Please. (while casting uneasy glances at the toppling pile of winter squash that has *magically* appeared on the counter)

Yes. Squash is a serious point of tension this time of year. I can’t help myself. I love the stuff. Mashed, roasted, simmered in soups or baked into pies – it’s all good in my mind. Fall rolls around and with it comes an insane urge to wack open a squash, sprinkle it with brown sugar, and pop that bad boy into the oven.

By the way, if you’ve never done that, what are you waiting for?

Every year I promise to try to keep it down to once or twice a week. I usually fail.

 This year the only promise I am making is to attempt to keep variety in our squash filled lives.

 And with that variety comes this incredibly rich and decadent pie. A pumpkin pie in it’s essence but features, instead, my favorite: butternut squash. Topped off with a chocolate studded streusel-y crumble that turns this pie into pumpkin pie’s exotic cousin.

Finish this off with a (generous) dollop of whipped cream and you will be in for a real treat.


Chocolate Harvest Pie Recipe

Yield: 8 servings

Prep Time: 30 minutes

Cook Time: 2 hours

Total Time: 2 1/2 hours


1 large butternut squash, halved and seeded (about 2 1/4 pounds)
Cooking spray
1/2 cup fat-free evaporated milk
3/4 cup granulated sugar
2 large eggs
1 teaspoon vanilla extract
1/2 teaspoon ground cinnamon
1/8 teaspoon ground allspice
1/8 teaspoon ground cloves
1/4 cup all-purpose flour (about 1 ounce)
1/4 cup packed dark brown sugar
2 tablespoons chilled butter, cut into small pieces
3 Tablespoons of semi-sweet chocolate chips
2 Tablespoons of rolled oats
1/2 recipe of pie crust (see notes) or ½ package of refrigerated pie crust such as Pillsbury


Position oven rack to lowest setting. Preheat oven to 400°.

Place squash, cut sides down, on a foil-lined baking sheet coated with cooking spray. Bake at 400° for about 35 minutes or until squash is tender. Let cool slightly and remove skin. Mash the squash pulp and measure out 2 ½ cups. Combine the pulp and evaporated milk in a food processor and process until smooth. Add granulated sugar and next 5 ingredients (through cloves); process until smooth.

Increase oven temperature to 425°

Heat a small skillet over low heat and add rolled oats. Toast the oats, tossing occasionally until lightly toasted, but not burnt. Set aside.

Lightly spoon flour into a dry measuring cup and level with a knife. Combine flour and brown sugar in a medium bowl and cut in butter using two knives or a pastry blender (I prefer a pastry blender). Add chocolate chips and toasted oats and toss to combine.

If using dough that was made the day before, allow dough to sit at room temp for 30 minutes before rolling. Roll the dough into a 13-inch circle and fit into a 9-inch deep-dish pie plate coated with cooking spray. Fold edges under and flute. Pour squash mixture into prepared crust. Place pie plate on bottom rack and bake at 425° for 15 minutes. Remove pie from oven.

Reduce oven temperature to 350°.

Sprinkle the flour mixture evenly over filling and shield edges of pie crust with foil or pie guard. Return pie plate to bottom rack and bake an additional 40 minutes or until center is set and no longer jiggling. Allow pie to cool completely on a wire rack. Slice pie and serve with a generous dollop of whipped cream.

Eat and enjoy!


Not-So-Basic Pie Crust

Adapted from Sarabeth's Bakery: From My Hands to Yours

Not being a fan of traditional, flaky pie crust, I was thrilled to come across this recipe in an amazing baking cookbook, Sarabeth’s Bakery: From My Hands to Yours. The process of making this pie crust, creams the butter, instead of keeping it in small pieces to create flaky layers. The result is a tender, but not especially flaky crust. Feel free to use your favorite crust in place of this recipe (either homemade or store bought).

This recipe makes enough crust for two pies (bottom crusts only) or one pie with a double crust. The dough can be made and refrigerated up to 1 day ahead of time, or double wrapped in plastic and frozen for up to 2 weeks. If using frozen dough, thaw disc in the fridge overnight, and allow to sit at room temp for 30 minutes before rolling out.


14 Tablespoons (1 ¾ sticks) unsalted butter room temperature

1/3 cup of whole milk

2 ½ cups of unbleached all purpose flour (such as King Arthur)

1 Tablespoon + 1 teaspoon of granulated sugar

¼ teaspoon salt


With the paddle attachment of a stand mixer, beat the butter on high speed until smooth and fluffy, about 2 minutes.

With the mixer on medium, slowly add the whole milk and beat until combined, pausing to scrape the bowl as needed. The mixture will be fluffy and shiny, although don’t worry if not all of the milk is incorporated.

Whisk the flour, sugar and salt together in a small bowl. With the mixer on low, gently add the flour mixture and beat until the dough comes together and the bowls sides become clean. Turn the dough out onto a floured surface and knead a couple of times until you have a nice, smooth ball of dough. Divide dough in half and shape each half into a disc. Wrap each disc in plastic wrap and refrigerated for 30 minutes before rolling out.

The dough may be refrigerated for up to 1 day, or double wrapped and frozen for up to 2 weeks. Thaw frozen dough in the fridge over night, and allow to sit at room temp for 30 minutes before rolling out.

Filling adapted from Cooking Light
September 19th, 2012

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4 comments on “chocolate harvest pie”

  1. This pie is just gorgeous and so inventive! It’s barely even spring yet with this pie in mind, I now can’t wait for autumn to arrive again cause I’ll definitely be making this lovely pie.

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