Super simple, super quick, and super delicious. This grain-free chocolate chess pie is all those and more, because it is also allergy-friendly and perfect for modern pioneers who want something sweet but healthier! In my quest to make every kind of pie, chocolate chess pie was on the list even though I didn’t really know what it was. I figured, hey, anything that has butter, chocolate, and sugar has to be good, right? And this pie was! It was perfectly chocolatey, had an amazing moist and smooth texture, and was insanely easy to make!

This post may contain affiliate links. See our Disclosure for more information.

Pioneer Recipe

Chess pie is a pioneer recipe. When I first set out to make a chess pie, I quickly learned that it is a classic southern recipe. The recipe has been around since the 17th century and it very well could have been a pie that the early pioneers whipped up, given its simple ingredients and how quick and easy it is to make. At least, I’m sure the southern pioneers made this pie!

Aside from being a pioneer recipe, this particular chocolate chess pie is a great modern pioneer recipe too! I did a little tweaking on the ingredients to make them more conducive for a low-inflammation, allergy-friendly diet. Traditional chess pie usually calls for a lot of sugar. Instead, I decreased the sugar (although I still used more sugar than I usually do in my recipes) and used a healthier sugar. Coconut sugar is sweeter than most traditional sugars and it does not have a tendency to cause blood sugar spikes since it metabolizes slower.

After editing the sugar in the chocolate chess pie, I also went ahead and made the rest of the ingredients allergy friendly. Since the ingredients are all very simple, it wasn’t very hard to convert this traditional pioneer recipe into a healthier modern pioneer recipe. This chocolate chess pie is…

• grain-free
• gluten-free
• tree nut free
• corn free
• dairy-free option

Sorry egg-free pioneers, unfortunately this pie is not egg free. Instead, I think the eggs are essential to the consistency and texture of this pie, so I’m not sure how using an egg substitute would work.

What is a Chess Pie?

You may still be wondering, what exactly is a chess pie? If you’re from the south, then you can just skip on over this section since more than likely this is all old news to you.

For those of you who have never heard of a chess pie (like I had), this section will give you a good idea of what to expect when you take your first bite of this pie! My well-meaning cousin described this chocolate chess pie in this way: “It tastes like a brownie pumpkin pie”. I said, “You know what, I think you nailed the taste and texture exactly!”. That’s a very accurate description of the taste and texture of this chocolate chess pie. It has the custard, soft, smooth texture of a pumpkin pie with the chocolaty, sweet taste of a brownie pie.

In the history of chess pies, it has been traditionally described as a “cheese’less cheesecake”. Original chess pies are made with simply eggs, butter, sugar, and some flour. Over the years, many variations of the chess pie have been created, including lemon chess pie, chocolate chess pie, and vanilla chess pie.

Personally, if I’m going to have a super sweet pie, I want it to have a dominant flavor, and chocolate was the perfect answer for this chess pie recipe flavor!

Pioneer Pies

I have been actually very surprised to learn about the amount of pies that could be considered pioneer recipes. Apparently the early pioneers had a likening for pies just like I do! Everything from meals to desserts could be turned into a pie. Simple pies with traditional ingredients are what pioneer pies are made out of.

Some unique meal pies that I came across include red bean pie, potato pie, and onion pie. I had never thought of turning white potatoes, beans, or onions into a pie, but they sure sound good! Other meal pies that sounded more familiar to me included chicken pot pie, venison pie, shepherd’s pie, and quiche (basically an egg pie).

Of the dessert-based pies, I was more familiar with those. Some of the ones on the list are even my favorites! Here are some pioneer pies you can try out for dessert:

• Grain-free apple pie
• Dairy-free sweet potato pie
• Lemon pie
• Mincemeat pie
• Chess pie
• Vinegar pie
• Shoofly pie
• Bread pudding pie

Storing & Serving

Chess pie was so rich and sugary, it was said that it could be stored in a pie chest rather than the fridge. Which was good for early pioneers who didn’t have access to a fridge. However, for modern pioneers, we have other options for storing our pie. And thank goodness, since I’m not sure I would want to eat something that sugary!

For this chocolate chess pie, you must make sure it is completely cool before storing it. Once the pie has cooled, you can either store it at room temperature for 2-3 days or in the fridge for 4-5 days. Either way, you must cover it with an air-tight covering. I use plastic wrap but I also try to use an eco-friendly alternative whenever I can. I love these silicon pot covers that stretch and seal over pots, pans, and pie plates!

As for serving the pie, it is generally recommended that you serve the pie when it is cool, however, I think this chocolate version would be delicious served warm too! I think the main reason behind letting it cool completely before serving is so that the pie will hold its shape when it is cut and served.

Traditionally, this pie is not served with any toppings. But, being a modern pioneer, I couldn’t help but add some of my favorite toppings! This chocolate chess pie is delicious with dairy-free coco-whip or dairy-free ice cream! Then again, I had it plain too and it was just as delicious!

Recipe Tips

This recipe is super simple and super easy! I whipped this pie up in one evening when I wanted to make a quick pie that was allergy-friendly for an upcoming family gathering. I was able to make everything, both the grain-free pie crust and the pie filling in just over 30 minutes. Not bad for a pie! To ensure you chess pie making experience is a success, here are a few recipe tips:

• For grain-free pie crust options, check out these two grain-free pie crust recipes. I like the pastry crust the best since it pairs well with the chocolate filling and is super quick and easy to make.
• Having all your ingredients at room temperature will help them all incorporate better.
• You can use coconut oil instead of butter in this recipe to make it dairy-free.
• Any dairy-free milk alternative can be used in this pie. My favorites are coconut milk and oat milk.
• Arrowroot flour and cassava flour are two flours you could probably use as a substitute for the tapioca flour.
• You can use cocoa powder instead of cacao powder. I chose cacao powder since it is basically cocoa in a less-refined state.
• The batter will seem very runny and soupy when you pour it into the pie crust. Don’t worry, it bakes up nicely and leaves you with a perfectly set-up pie.

A pie that uses simple ingredients, is allergy-friendly, can be made in a half an hour, and is super delicious….I’m sure you are just dying to get the recipe! Well here it is, this grain-free chocolate chess pie will make your day (and whoever else you share it with)!

Where to Find the Ingredients

• Bob’s Red Mill tapioca flour
• Nutiva coconut sugar
• Navitas cacao powder
• Simply Organic vanilla extract
• Pacific coconut milk
• Pacific oat milk
• Supplies: 9″ glass pie plate

With a rich, chocolatey taste like a brownie pie and a smooth, creamy texture like a pumpkin pie, this chocolate chess pie is going to be a hit! It is the perfect allergy-friendly dessert that can be thrown together in minutes and has a taste that everyone is sure to love. In my opinion, the best part is that this is a pioneer recipe that is super simple to make and tastes amazing!

Need more amazing pioneer recipes or resources? The make sure you jump on the modern pioneer chuckwagon (aka. our weekly newsletter)! You’ll immediately get our free pioneer cookbook as well as new weekly recipes delivered right to your inbox! That’s what I call pioneer baking and cooking made easy!

by Alexa