Chocolate Chess Pie

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Chocolate Chess Pie by The Wood and Spoon Bly by Kate Wood. This gooey fudge pie is a take on the classic Southern recipe. Make with a flaky pie crust and a cocoa powder fudgy filling, this pie is topped with chocolate whipped cream and chocolate curls. Definitely the prettiest pie you'll see this holiday season. Make this pie for Christmas or Thanksgiving as it serves a crowd and is great for sharing. Find the recipe and other old South recipes on thewoodandspoon.com

With Thanksgiving just around the corner, I figured y’all might need a sure thing. A dessert that is rich enough, easy enough, pretty enough, and able to feed enough mouths at your dinner soirees. A dessert whose plate gets cleaned and leaves party guests licking their forks and asking, “Who brought that?” This chocolate chess pies is most certainly a sure thing and I can’t wait to tell you all about it!

I’m guessing that a lot of you are puzzled about chess pies right now, and I’d bank that most of the confused folks reside somewhere north of the Mason-Dixon Line. Prior to moving to the South, I didn’t have a clue either. Ten years in Birmingham wasn’t long enough for me to dig up the deep Southern roots of chess pies, but upon marrying into my husband’s Alabama family I learned quickly that chess pies are king.Chocolate Chess Pie by The Wood and Spoon Bly by Kate Wood. This gooey fudge pie is a take on the classic Southern recipe. Make with a flaky pie crust and a cocoa powder fudgy filling, this pie is topped with chocolate whipped cream and chocolate curls. Definitely the prettiest pie you'll see this holiday season. Make this pie for Christmas or Thanksgiving as it serves a crowd and is great for sharing. Find the recipe and other old South recipes on thewoodandspoon.com

Prepared with a single crust and a custardy filling made primarily of butter, sugar, and eggs, chess pies are rich, dense, and ultra-sweet. Although a number of variations of chess pies exist (Buttermilk! Pecan! Citrus!), anyone who is anyone knows that chocolate is the one to beat. If you disagree, we can’t be friends. Just saying.

A few years ago, I ran across my husband’s grandmother’s box of recipes. They were beautiful, worn with stains and torn edges, and spoke to the culture my husband grew up in. Brett’s Nana was a hard worker and spent a lot of time loving her tribe through the food she prepared- fried pork chops, skillet cornbread, and warm banana pudding. One of my husband’s favorites has always been his Nana’s chocolate chess pie, so finding that recipe was nothing short of a treasure. 

Chocolate Chess Pie by The Wood and Spoon Bly by Kate Wood. This gooey fudge pie is a take on the classic Southern recipe. Make with a flaky pie crust and a cocoa powder fudgy filling, this pie is topped with chocolate whipped cream and chocolate curls. Definitely the prettiest pie you'll see this holiday season. Make this pie for Christmas or Thanksgiving as it serves a crowd and is great for sharing. Find the recipe and other old South recipes on thewoodandspoon.com

I adapted her time-tested notes to create this chocolate chess pie recipe. Using a bit less sugar and a tad more cocoa, I wound up with a pie that was nostalgic and special for my hubby, yet suitable for my own tastes. Even better, this chocolate chess pie is a cinch to make and bakes up terrifically every time. 

Chocolate Chess Pie by The Wood and Spoon Bly by Kate Wood. This gooey fudge pie is a take on the classic Southern recipe. Make with a flaky pie crust and a cocoa powder fudgy filling, this pie is topped with chocolate whipped cream and chocolate curls. Definitely the prettiest pie you'll see this holiday season. Make this pie for Christmas or Thanksgiving as it serves a crowd and is great for sharing. Find the recipe and other old South recipes on thewoodandspoon.com

To prepare it, we start with the crust. Sure, you could buy a crust from the freezer section of the store, but GUYS, we are cool and proficient enough to make them ourselves. Check out my favorite recipe here or choose one of your own. A single crust is all that is required for this recipe, so save the other half of your double crust for later. Roll the dough into a shallow 9″ metal pie plate and crimp the edges. Give it a brush of an egg wash for color and gloss, and set it aside in the fridge while you prepare your filling. Cocoa powder, sugar, salt, and the tiniest bit of flour are whisked together in a large bowl before the liquid ingredients are added. Melted butter, eggs, and evaporated milk are stirred in next, whisked in until the mixture is uniform throughout. Pour the filling into the prepared pie pan and allow it to bake in the oven.

Chocolate Chess Pie by The Wood and Spoon Bly by Kate Wood. This gooey fudge pie is a take on the classic Southern recipe. Make with a flaky pie crust and a cocoa powder fudgy filling, this pie is topped with chocolate whipped cream and chocolate curls. Definitely the prettiest pie you'll see this holiday season. Make this pie for Christmas or Thanksgiving as it serves a crowd and is great for sharing. Find the recipe and other old South recipes on thewoodandspoon.com

The hardest part of this chocolate chess pie is identifying when it’s done. After about 35 minutes, you should find that the pie has risen slightly and is only barely jiggly in the center half of the pan. The pie will definitely look underdone when you remove it from the oven, but just cross your fingers, say your prayers, and all will be well. Chocolate Chess Pie by The Wood and Spoon Bly by Kate Wood. This gooey fudge pie is a take on the classic Southern recipe. Make with a flaky pie crust and a cocoa powder fudgy filling, this pie is topped with chocolate whipped cream and chocolate curls. Definitely the prettiest pie you'll see this holiday season. Make this pie for Christmas or Thanksgiving as it serves a crowd and is great for sharing. Find the recipe and other old South recipes on thewoodandspoon.com

Once the pie has chilled to room temperature, you will have created the most perfect chocolate chess pie! Truly, you could stop there. You could give it a dust of powdered sugar or just throw it on the Thanksgiving table and call it a success. But I know you. Like me, you love to take things too far. So lucky for us (read: everyone who eats this pie), we instead go overboard and add a super fluffy, perfectly sweetened chocolate whipped cream. The billowy clouds of cream and air add another layer of flavor and a whole lot of flair to an otherwise dull-looking pie. Who doesn’t like whipped cream!?! Trust me on this one, okay? Chocolate Chess Pie by The Wood and Spoon Bly by Kate Wood. This gooey fudge pie is a take on the classic Southern recipe. Make with a flaky pie crust and a cocoa powder fudgy filling, this pie is topped with chocolate whipped cream and chocolate curls. Definitely the prettiest pie you'll see this holiday season. Make this pie for Christmas or Thanksgiving as it serves a crowd and is great for sharing. Find the recipe and other old South recipes on thewoodandspoon.com

I’m sure you’ve already got a stellar lineup of treats for this Thanksgiving, but I want to encourage you to give this pie a shot. It is excellent and 100% worth the very few minutes it will take to make it. And if you’re in the mood for more pies, be sure to check out the list of my blogger friends below who are sporting pie recipes today. The self-proclaimed #piesquad is back again, ready and raring for action, so give some recipes a try and let me know what you think! Happy Friday to you all!

Cloudy Kitchen

Chocolate Cream pie with whipped peanut butter cream

 

Cook Til Delicious

Pear Cranberry Frangipane Tart


DisplacedHousewife

Five-Spice Cran-Apple Handpies

 

The Farmer’s Daughter

Apple Ginger Pie

 

 

Harvest and Honey

Apple Apple Pies


Lyndsey Eden

Maple Cream Cheese Pear & Pistachio Galette


Salvialimone

Tarta Tine with White Chocolate Caramelized Pears

 

TermiNatetor Kitchen

Brown Butter Chai Pumpkin Pie with Sugared Sage


Topless Baker

Apple & Blackberry Flower Lattice Pie

Chocolate Chess Pie by The Wood and Spoon Bly by Kate Wood. This gooey fudge pie is a take on the classic Southern recipe. Make with a flaky pie crust and a cocoa powder fudgy filling, this pie is topped with chocolate whipped cream and chocolate curls. Definitely the prettiest pie you'll see this holiday season. Make this pie for Christmas or Thanksgiving as it serves a crowd and is great for sharing. Find the recipe and other old South recipes on thewoodandspoon.com

If you like this chocolate chess pie, you should check out:

Mocha Hazelnut Cream Pie

Pumpkin Cheesecake Tarts

Banana Coconut Chocolate Cream Pie

Chocolate Chip Bundt Cake

Chocolate Caramel Crumble Cake

 

Print

Chocolate Chess Pie

Chocolate Chess Pie by The Wood and Spoon Bly by Kate Wood. This gooey fudge pie is a take on the classic Southern recipe. Make with a flaky pie crust and a cocoa powder fudgy filling, this pie is topped with chocolate whipped cream and chocolate curls. Definitely the prettiest pie you'll see this holiday season. Make this pie for Christmas or Thanksgiving as it serves a crowd and is great for sharing. Find the recipe and other old South recipes on thewoodandspoon.com

This chocolate chess pie is a traditional southern favorite, rich and fudgy, with the added oomph of a fluffy chocolate whipped cream. 

  • Author: Kate Wood
  • Prep Time: 15
  • Cook Time: 30
  • Total Time: 45 minutes
Scale

Ingredients

For the pie:

  • 1 recipe for a single unbaked pie crust (not deep-dish)
  • ¼ cup (30 gm) cocoa powder
  • 1 tablespoon flour
  • 11/4 cups (250 gm) sugar
  • ¼ teaspoon salt
  • ½ cup (113 gm) unsalted butter, melted
  • 3 large eggs, beaten
  • 3 tablespoons evaporated milk
  • 1/2 tablespoon vanilla extract
  • ½ tablespoon vinegar

 

For the chocolate whipped topping:

  • 11/2 cups (360 mL) heavy whipping cream
  • ¼ plus 2 tablespoons (75 gm) sugar
  • ¼ cup (30 gm) cocoa powder

Instructions

To prepare the pie:

  1. Preheat the oven to 350 degrees.
  2. Using a rolling pin, roll out the pie dough and transfer it into a 9” pie plate. Gently press the dough into the edges of the pan and trim off any excess. Crimp the edges as desired.
  3. In a large bowl, whisk together the cocoa powder, flour, sugar, and salt until combined. Add the melted butter and sitr just to combine. Add the eggs, evaporated milk, vanilla extract, and vinegar and mix to combine. Pour the filling into the prepared pie crust and brush the crust with a bit of milk, beaten egg, or cream if desired. Bake the pie in the preheated oven for about 35 minutes or until the edges are well set and the innermost circle of pie is still just a bit jiggly. Remove and cool to room temperature.
  4. Once cooled, prepare the whipped topping. Beat the heavy cream on medium speed in the bowl of a stand mixer fitted with a whisk attachment. Whip until frothy and slightly thickened and add the sugar and cocoa powder. Increase to high speed and beat until stiff peaks form. Spread dollops of the whipped cream on top of the pie and serve immediately.

 

43 thoughts on “Chocolate Chess Pie”

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  4. Hi! I made this pie and really like it; however, the chocolate flavor doesn’t really come through. Is there a specific cocoa powder you would recommend? Also, I am having an issue with the amount of time I should bake it because I am unsure of what consistency to aim for…any thoughts? Thank you so much!

    1. It’s not SUPER chocolatey in flavor. Def chocolate, but overall just SWEET. Super Southern. I pull my pie out of the oven when it’s no longer jiggly, the top is firm (but not hard) to the touch, and there are a few cracks beginning to form on top.

  5. 2018 (Wife’s) Family Annual Pie Day Champion!

    The pie was amazing. Not only did it win the regular vote – It even tied for first in the Prettiest Pie category. And I bet I spent a fraction of the time that the other entrants did. Really easy to make.

    I am the only male entrant in this contest every year, and this is the first time I have won. (To be honest, there were a lot of amazing pies there, but my strategy of letting the fruit and pumpkin pies split the votes was a good one!)

    Thanks for the great recipe. Happy Thanksgiving!

  6. This pie is FANTASTIC! Chocolate chess is one of my all-time favorites, and this was the best I’ve ever tasted. Seriously. The actual pie was rich and fudgy and delicious, but with that ridiculous chocolate whip on top, good lord stop me. I took it to a family dinner and everyone kept saying it was the best chocolate chess they’d every tasted. So…I’m now a hero. Thanks Kate! 🙂

  7. This pie tastes amazing! I did have a problem with the pie crust though. When I took it out of the oven, a large air bubble had formed in the crust so very little filling was on that part. Although it’s not a huge deal, I couldn’t serve part of the pie. I was wondering if next time I should poke holes in the crust?

    1. Interesting! You know, this has happened to me one time with another custard-ish pie in the past and I think it may be because the filling isn’t quite heavy enough to keep the pie weighted down. I would be hesitant to poke holes on the bottom with this liquid of filling as it may seep under the crust. If it happens again, I would instead blind bake the pie crust using pie weights for a few minutes, then pour the filling in and continue baking. If the rim of crust gets too brown you could always just make a pie collar with foil to protect it. I hope this helps! 🙂

  8. Found your recipe while searching out chocolate pie recipes. I made this for our Pi Day celebration at work… and won first place out of 14 pies. Awesome!

    I, too, found that the filling separated after baking. No one complained, and it definitely didn’t compromise the flavor. I did stick it in the fridge for a bit after topping and before serving – maybe that has something to do with it. I will definitely make this again.

    Thanks!

    1. Zack! I am thrilled to hear that you won the pie celebration! How fun!

      I am less than thrilled to hear that the pie separated on you. I reached out to some pie experts to try to narrow down why this happens. You are not the only one! I am told that it is really important to use room temperature ingredients to keep the pie filling stable. I guess everything going into the pie the same temp helps to meld it all together.

      I hope you’ll give this pie another try! I’ve never had that happen and am determined to make sure everyone else has success too!

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  10. Made this pie today for Thanksgiving. Omg. This pie is amazing. Maybe best ever. Mine separated into a custard later and a chocolate layer while baking – don’t know why it did that yet, but even so, it looked so lovely and blew everyone’s minds. Thank you for this post!

    1. Hi Kara! I have done some research on the pie separating issue. You are not the only one! I am told that it is really important to use room temperature ingredients to keep the pie filling stable. I guess everything going into the pie the same temp helps to meld it all together.

      Anyways, I hope you’ll try it again and am glad you were able to enjoy it anyways. 🙂

  11. This pie looks fantastic!! Is it possible to bake it a day a head of when I need it and then make the whipped topping right before serving? Or do you think it’s best to make it all on the same day?

      1. Thanks so much, Kate!! I saw this pie and decided it was destined for our Thanksgiving table. I really enjoy your blog and my family requests your Funfetti cookies constantly, they’re on my Instagram feed frequently 😄

        1. Jacqueline- this warms my heart! I’m thrilled that you’re enjoying the recipes. I love making new friends here! Happy thanksgiving!

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  13. Hi Kate

    You have a lovely blog. I’m a fan of the colours and your photos are stunning. I’m a Northerner (North of the Mason Dixie line) but my fiance and his family are from Alabama & Georgia. I think I’m gonna try this recipe as a surprise. Thanks for sharing it. I’ll let you know how it goes 🙂

    1. oh, thank you for the kind words!! i can’t wait to hear how he enjoys the pie. what a thoughtful thing! be sure to tell me about it!

  14. Kate, this pie is absolutely dreamy. I’m in love. Handwritten old family recipes are the best- I have several scanned copies of humble notecards with my grandmother’s writing that look very similar and they are some of my most treasured treats. Thank you for sharing this and I can’t wait to try making my first chess pie!

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